What Still Lies Between

Now you have most of the good stuff so it’s time I get through the pieces that are still floating in my head as challenges.

This part I find to be my self -talk-therapy. I’ve got questions to suss through and I often find myself stepping back from Scott to think: can I do this?

Here’s my running list of what lies stuck between my heart and my head ….

Attraction and Sex: The attraction piece is not fully vetted. I do find myself becoming more attracted to him and wonder if that’s from familiarity.

Sex has improved although there is still some sort of missing component for me. I get turned on by Scott, that is never an issue (so there clearly is an attraction) but at some point during the act, I become too aware that I might not like something. We have started talking about this a little more because I believe he senses it as (from me) well. I’m having a hard time with orgasm. He’s gotten me there a couple times, but not enough for the amount of time we are together. I’m afraid because I’m frustrated I’m not asking for more oral sex and he’s not offering. Our sexual styles are very different. He is so very far behind my more skilled partners that it worries me. Perhaps it’s not that he’s less skilled, it’s just less in sync with me? Either way, something is off.

Part of me balks at talking about “how” I like to have sex. I can absolutely say what I don’t like when it happens, but guidance on what I do like I find much harder. It’s not a recipe. I hate being a teacher with such a passion (my baggage from my marriage) and frankly I’m a horrible teacher. He’s not super intuitive and because early on there was way too much I didn’t like about his style that I’m going to guess he’s holding back in some ways.

I think this is the greatest challenge.

Bravado/Bragging/Gossiping: Without writing a novel and being over descriptive (which I know I tend to do) I’m just going to list a few of the consistent behaviors he exhibits:

He can sometimes behave very immaturely for a 46 year old man and he tends to spend too much time with much younger people in a different place in life.

While he thinks he avoids drama like the plague, he in fact, invites it in. It’s the sheer nature of his personality to pretend not to be involved when he is entirely involved. Like not gawking at a traffic accident and perhaps then even causing your own. He attracts drama. This one I understand. I know this because it’s shit I’ve done with men. But he doesn’t just do it with women but also the kids he hangs around with.

He doesn’t think he brags but he does. Pride is ok when it’s subtle. He wants people to know what he’s accomplished and he needs the affirmation. I am not used to anyone talking about themselves in this manner. I find it very off-putting and don’t really know what to make of it.

The gossip – that’s something I’ve never done and it really leaves a bad taste in my mouth. He talks to a lot of people and feels like he keeps his most personal information close to his chest. He just doesn’t realize he reveals all of himself in so many other ways than the actual words. To compound this, his 24 year old daughter is busy telling everyone anything else he hasn’t told them. He does the same thing in his personal and professional life. I have my close friends or family (and of course this blog) that I share personal info with and even then, not always outright. Maybe I’m just not as friendly and open. His job allows him enough down time (breakfast breaks, coffee breaks, lunch breaks) that it’s ripe for water cooler gossip. Again, I’m not used to this amount of free time in an office environment.

I know that sounds demanding and I’m not sorry about it. I want him to act his age with or without me beside him. He is super intelligent but the problem is being surrounded (in his social life) by a different class of people than I’m used to. If you don’t think class systems still exist, you’re nuts. And I’m not talking money. This is only related to behavior. He may have been born a hillbilly but he doesn’t need to act like one at 46.

This is a fine line. Where he lives and where I live are very different. When he’s up here with me he exhibits NONE of this nonsense. He sees it won’t fly here. My concern is seeing how much of this is ingrained in his personality. What’s the saying? You can take the boy out of the country but you can’t take the country out of the boy. Still unsure about the overall impact of this one so I do my best to sit back and absorb what he shares with me with as little judgement as possible.

Socioeconomic: now this is the one related to money. Seeing how he lives was eye opening. He has a great life and does earn plenty for what he wants from his life. This is partially due to location and partly due to ones desire for things/experiences. I’m happy I got to see this first hand. He’s not cheap by any means. The word (we both) came up with for me is Bougie. It’s the same exact word Tony used for me. I have certain ways/things thats I’m Bougie about. I turn my nose up when someone/something isn’t held to whatever that Bougie standard is for me. The good news is I realize the $ is a figure, that’s it, a $ figure. It doesn’t define anything. Sure more money opens more doors but Scott doesn’t care if those doors open for him. I’m still trying to figure out how much it matters to me. Spending time with him in his lovely home, in his life, showed me I really need to evaluate how I truly feel deep down about money. I’ve been spoiled and jaded a long ass time. This remains ultimately unresolved but is no longer a check against Scott if that makes any sense.

That’s pretty much it – not so very different than the initial feelings I identified with him, but softened by the fact he’s such an amazing person and cares for me so much. I need to work through these so they don’t come back to bite me as resentments later – that much I know from my bad marriage.

I do often feel a pull towards him emotionally, I really like him for so many reasons. The negative ones listed above seem to have a pretty firm grasp on me and will certainly require working through. I’m just attempting not to let them override the deeper sense of satisfaction.

Frankly, the biggest red flag in all of this I haven’t even listed because I understand it and think it can be possible, though improbable. Scott fell in love too quickly and already sees our future together. I worry that he’s doing a bit of a dance around my personality because he sees what he wants to see instead of seeing what’s in front of him. Then I question that because he will stop me when he doesn’t like a behavior of mine and I think “oh, he really is taking all of me in and accepting me.” The jury is out on this until we have time under our belt. I hope he doesn’t have too much of a fantasy of me built in his head that, as we spend more time together, comes crashing down into a reality he wasn’t expecting. Only time will tell.

What it Feels Like to Let Go

Since that day in September where I truly decided I was going to give Scott an honest chance, it’s been nothing but easy happiness in our relationship.

As KDaddy rightly suspected, I’ve said some things that are not so nice, and Scott seems to take them in stride and find a way to talk to me about them. One thing that absolutely has not happened is Trixie surfacing. She’s got no place here and no reason to surface, but somehow I also know I’m prone to be crazy. The single most recurring thought I seem to be having is “I would like to see this work” which, in turn, provides my brain with enough pause to keep my mouth (mostly) shut and make better choices. Something has changed in me that is preventing my normal self-sabotage.

Sure, it crosses my mind that I had dating lethargy and little success this last year. The fact that I’m at such a low point emotionally due to my job/financial situation also causes some concern. I don’t think I’m with Scott because I’m settling, bored or lonely. I think I’m with him because he is slowly stitching together the napalm blasted hole in my heart left behind by Tony. Scott makes me feel good about myself and is unencumbered by a marriage. None of the previous men I’ve spent longer amounts of time with were free to pursue me. Each of them took so much from me, and while I felt I was getting something back emotionally from them, the fact was they were taking more than I could ever receive. I truly didn’t realize how damaged I have become, how high the walls were built. I thought I was wide open for relationship and kept making excuses why this one or that one wasn’t right for me.

I really wasn’t ready and didn’t see it. I’m a bit unsure if I’m truly ready now, but Scott is able to somehow see and understand that I’ve been emotionally unavailable and has been patient with me and whatever pace I’m going.

He also says he’s in love with me.

On our first night together at his home, as we fell into bed, the “you know I’m in love with you, right?” came out in such a rush and with such forceful intent that I knew he was really trying to hold back, but the emotion overwhelmed him entirely. I think he was so worried about what I would say or do that he began to sort of shrink back from me. I pulled him close, whispered “I know and I can feel it” and then we “made love” for the first time. He became emotional again during sex and declared a clear “I love you” and we absolutely shared a tender session. Afterwards he sort of offhandedly mentioned he wasn’t used to sex like that. Sex where he was so close to someone and could feel how the other person shared a strong emotion or bond with him. He said he never wanted to feel that close connection before. I didn’t press, I listened and we soon fell asleep. My feeling was he was very anxious about his declaration and then subsequently surprised and pleased with my response.

We had a lot of fun while at his home and I was very comfortable. I’m not going to write about his daughter as there’s still some story there to uncover about how she really felt. Generally speaking she was watching me like a hawk and very angry her cats needed to be locked in her basement apartment the entire time I was there. It’s a beautiful 1 bedroom apartment in a walk out basement. They had plenty of room. She called it animal abuse. He’s told her that’s how it’s going to be when I’m there, full stop, no negotiation. So, like I said, more to uncover there as she separates how she feels about her cats and how she feels about her Dad having a woman in his life.

We didn’t do most of what we planned to do and spent a lot of time just enjoying each other with simple activity. Making dinner together. Sharing coffee on the deck. Taking a lot of walks. Binge watching a show after the half marathon so we didn’t have to get off the couch. Some nights at the bar. Some nights at home. I’m repeating myself by saying it was easy but there’s no better word for it.

I didn’t want to leave when it was time to go. I felt tugging at my heartstrings and I almost cried. By the time I made the 5 hour train ride home and settled in, we had agreed he would come to me in 2 days and spend a long weekend

So we have basically spent the last 2 weeks together full time. I’ve never done that with any man besides my x husband.

I’m sure I’m going to think of a thousand things to write and forget a thousand more, but the real point is we are still smiling and still wanting more time together. Because of the distance we have both explained to our children that they can expect house guests for some time as we figure things out. Talk about a big step for me, the boys only ever bumped into Tony. They are not thrilled about it but they understand why it’s going to be this way.

I did have a conversation with Scott about exclusivity. You just never know these days. I’m pretty sure there hasn’t been anyone else for him since he started seeing me again this summer, but there was for me (though I didn’t say) and I wanted him to know I considered this a monogamous relationship. He “formally” asked me to be his girlfriend as silly as that sounds. I just felt better having a clear Conversational about exclusivity. The reasons are multilayered but include not wanting to take something for granted, wanting to give it proper identification in my own head and, I believe, give him peace of mind as he mentioned “whatever this is” several times to me. I did want him to know that this is a relationship, we are in it. The last night I spent with him at his home I felt like there was a moment where he was about to cry (it was dark and I couldn’t see, but I could sense the change in his voice) when he said he didn’t want me to leave because he was so afraid I would never come back, that it would be the last time. He was almost holding his breath when he said it. I could be very wrong, but I don’t think so – he was scared and the exclusivity conversation gave him a solid foundation. I’m in this with him, I don’t want him thinking that because I’m not in love with him that it doesn’t mean I’m not committed to our budding relationship and seeing how it grows and where this leads us.

That was a bigger step for me than I thought it would be.

Scott is a learning experience for me. A really joyous learning experience. I like how I feel and I like how I’m acting. I feel in control and happy. I don’t blurt out every thing in my head and share every dark secret, and I’m not lying either should he ask a direct question. He is just so very different from me that he takes some getting used to and the more time I spend with him the more I like him. It’s not easy for me to relinquish my imagined control of situations, and he tells me I still do it, but I can feel him gently navigating me and that feels ok to me.

Something Comfortable

I really thought I would have written more by now, but you know how life suddenly fills up the space and the time seems to disappear.

The time with Scott morphed into something other than the full, fun schedule we had planned. Something so much better. The high level view is I arrived on a Tuesday and we went to his local bar (he was so excited about this because no girl has ever been to his watering hole), we ran earlier than anticipated on Thursday, then we were dead on the couch for 2 days after the run so decided to stay home. From Friday until Tuesday we did a whole lot of nothing together. I ended staying until Wednesday. By the time I got home, he was fixing to drive back up to me by Thursday.

Was it the most exciting, heart-pounding never-want-this-moment-to-end time? No. not even once. That excitement isn’t present for whatever reason and I think I am going to have to accept that. I would love to have those butterflies again, but I think I’m just fine without them. More importantly, even without that excitement, I didn’t want to leave him. I found myself in his space fantasizing about how I was going to fit in – which is novel for me – prior to Scott, my feelings have always been how will this person fit into my life. Certainly not the other way around.

The strangest things happened to me during this trip. I let him tease me – like really give me the business (my x teased cruelly so I am very sensitive to teasing). For instance, I’ve been complaining about an extra 10 pounds and he picked me up one day and “oofed” loudly then exclaimed “there’s those 10 pounds!” And promptly cracked himself up. That comment could go way wrong and I found myself shocked in a funny way and then laughing because I knew this man was happy with me just the way I am. He makes jokes and facial expressions I just don’t like and in my head the comment is ready to fly, but it sits in my mouth, unmoving and unwilling to be released into the spoken air. Instead I step back and look at him with wonder at how comfortable he is with himself. Now he tries to crack jokes he knows I won’t laugh at because he finds my absence of reaction even more humorous. This has had the opposite effect on me, causing me to laugh when I don’t think the joke is funny but I think the fact he’s trying to make me “not laugh” is funny. For whatever reason, I do not want to unleash my normal negative commentary and actually find myself thinking before I speak so that I don’t hurt the man who is doing nothing but trying to please me.

This wasn’t a thought with Tony. With him I never had to think about it because he didn’t have characteristics that made me wonder if he was the guy for me. I wanted to be good to Tony because Tony was emotionally good to me. But Tony pales in comparison to Scott’s treatment of me. Never thought I would say that to be honest. I would be a fucking fool not to give Scott my full effort. I think that’s what’s holding back most of my negativity. What I find fascinating is how I recognize it. I see or feel something I don’t normally like and my heart/gut/brain (I don’t know which) have a sort of physical switch I hear in my head that says “don’t” he’s just silly and it’s harmless. A lot of times it says “just who are you trying to impress?”

We made it through 8 days, I went home for 2 nights and he was up at my house again for the past 3 nights.

We are both still smiling.

That’s pretty amazing, right?

Heading towards something new

I wrote this from the train headed towards Scott. It’s a long train ride, almost 5 hours. I would be happier if I didn’t have a migraine.

I have vacillated a bit over what I’m feeling. I want to believe I’m excited to see him but it doesn’t quite feel like excitement. At least, not the kind I’m used to. This isn’t white hot burning butterflies out of control excitement. This is new. I honestly don’t know what to call it. It’s a good feeling. Sort of like knowing what a good meal is going to taste like, comforting.

I am looking forward to being with him for an extended amount of time. I have no doubt we will have fun. I’m pretty sure I’m going to be comfortable. I don’t worry that he will pressure me to behave or do anything I don’t want to do, he won’t even have an expectation. Or, perhaps if he does, he probably won’t let it show. His entire goal will be my pleasure and comfort over the next week.

You heard that right – one week. I knew I was going to need to see Scott on his home turf to begin to understand if this relationship would have legs. I knew we needed some time that wasn’t feeling like vacation time. The opportunity presented itself and I took it.

We will be spending a few days at his home and then a few days in Washington DC. We are running The Virtual Chicago half marathon together on Saturday. This is a good example of how far he’s willing to go for me – the half marathon was something I wanted to do for myself because I needed some focus to pull myself up from a spiraling depression. When he heard I was doing it, he wanted to join me. He is a sincere athlete and will have to hold way back to run with me, but it’s all he wants to do – to do this together and share the experience. I admit, when he said he wanted to do it with me I was really pleased. Then he suggested we run it around the National Mall in DC and, while I’m terrified to run outside (because I just don’t), I love the idea of being somewhere so iconic to mark my first half and being with someone who is going to derive as much joy (and pain) from the experience as I will.

I wish I was the kind of hyper excited I used to get before seeing Tony or Bobby. I wish I felt those butterflies. Once in a while there is a little twinge of something, I wouldn’t call it the butterflies, but it is something. I know without a doubt I will be happy around him – the question remains: is that enough for me? Is it enough for anyone? I just don’t know.

I still consider the fact we are from different socioeconomic classes. I’ve been doing a LOT of reading about that and it’s well written about that it’s a pretty difficult struggle for most couple to overcome this kind of hurdle. I knew I wasn’t imagining things when I feel this way. Socioeconomic diversity is a real thing and a thing that can cause either partner to be unhappy for different reasons. The only way I am going to determine if this is a real-world challenge or a just an in-my-head challenge is to spend time with Scott, especially on his home turf.

I will also be meeting his 24 year old daughter. She is the light in his life and he’s so excited for me to meet her. She’s so happy for him that she’s excited to meet me as well. I think it’s strange and sweet all at the same time. It will be a first for me. They have a very tight relationship. She is lacking a mother figure and I think he sees what kind of influence I could be on his daughter. I don’t feel pressure right now because I don’t know what I want in this relationship other than for us both to enjoy one another.

He went crazy cleaning his house and food shopping for me. His daughter has cats and boy do I hate cats – so there was a big effort in his part to remove all signs of cat hair from the place. I am terrified of all cats so I hope his daughter doesn’t think it’s “cute” to let the cats out of the basement. That won’t go over well for anyone. When someone comes to my home, of course I prepare in much the same way but I have a feeling my home starts in a bit more organized place than his does. He’s been a bachelor for a few years and I know he doesn’t like it. He often hints how he doesn’t bother with things at home because he just assumes his “woman” is going to want to change things. In a way, he’s quite compliant to the traditional roles of man/woman in a relationship which is, in its own way, charming. I like this, it works well for me. He will always care for me.

We started talking about love languages but didn’t get too far other than retaking the quiz and sharing results. I was surprised that acts of service wasn’t his first or second love language as he often comments about the lack of what others have done before me. His top love language is quality time followed by physical touch and then acts of service. Interestingly enough, words of affirmation fell off the top of my list for the first time ever. I suspect this is because I’ve learned to affirm myself in so many ways. I realize I don’t need as much from a partner though I still love to hear it. Also, Scott says so much positive affirmation for me that I find it a little unbelievable. I can’t recall if Tony did it this much or not. I don’t think so. I actually wish he would pull back on the compliments a little so that they felt a little more true. My face, hair, outfit or whatever can’t be perfect every single time but that’s pretty much what he says if I so much as self-flagellate. My traditional go to moniker is usually “handsome” when I’m attracted to someone and I find myself holding this back with him and I feel pretty crappy about it. It doesn’t ring true to me. Little things like this tend to occupy my thoughts when I’m away from him. I’m really trying not to let them consume my thoughts.

In between this nonsense I am happy to be heading his way. As I get closer I am starting to feel a little excitement and I know when I see the happiness on his face I will respond in kind. I know we will have fun, laugh, be silly and enjoy one another. I feel like we can be friends together. I know this is all a great start.

I am so confused …. (part 3)

I think I got most of it all down and out now.

There are more good qualities than challenges with Scott if I was counting. I’m just not sure how the weighted average works out.

After we went away for the weekend and I agonized for a while as well as solicited advice from friends. I dug deep into what I was feeling and tried to explore why I was so predisposed to these thoughts and feelings. I came up with some answers and on some I’m still empty handed.

And it may surprise some of you …. but I firmly decided I was going to give it a go with Scott.

I just needed to wrap my mind around it. I was clear of the potential pitfalls but all of my friends, and I do mean all, unanimously voted for Scott. They know all of the struggles I’ve had and continue to go through and just felt that I deserved someone who adored me with no questions asked. And he does. He really takes me for who I am. Perhaps if there was one quality above all that I treasured in Tony it was this one. Scott has exactly the same quality.

He takes me for who I am knowing I struggle with his job/income and the stereotypes assigned to government work. He doesn’t know about the attraction piece, though we have talked about the disparity in class briefly. He acknowledges we started in very different places and have had significantly different life experiences. He treats me as if I am a prize that he never thought he would win and often seems to be in awe of me.

He has already told me he would move heaven and earth for me if I would just let him.

Scott is a good man. He tells me he has a mean streak that he doesn’t like about himself and I see that coming out as arrogance right now, but I believe him when he tells me, I just haven’t seen it. I can tell his defenses are down around me and I am allowing mine to begin to come down as well. Once I make up my mind about something, I go all in.

I do worry that I’m not always so nice and I can be a bitter pill to take. He seems good at deflecting this quality in me and it tends to have me loosen my reigns – which is very unusual for me. He doesn’t dig in in opposition to me but instead tries to offer alternative viewpoints without pressing me. My need to be right all the time is much less aggressive with Scott and this is unique. A little example of this is when we were walking along on our way to lunch on our weekend away, I stopped suddenly and said “we are going the wrong way!” He said he was pretty sure we were not. As per my usual always-right self I declared “I really think it’s the wrong way!” He asked me to trust him and I looked at him and rather than insist yet again, I just said “ok.” The funny thing was it stopped him in his tracks and he worried that now I would give it to him if he was wrong. I promised him I wouldn’t, that I did trust him and even if he was wrong it was just a little walk on a beautiful day and didn’t really matter. I meant it too. I handed over the reins. I let go. And, of course, he was right. He was also very relieved which was quite funny.

That was the first time I really put my trust in him. The next time was the long ride home in my car. He drove and I was able to fall asleep for a little bit. That’s a sure sign of trust with me. He told me much later how happy this made him because his x-wife and his x-affair partner both hated his driving. I know these are two very little things, but they are important to me. When I don’t need to be in control and I can let go I am happier. I know this for a fact after Bobby and Tony, but it takes a special person to get me to change my behavior. I don’t give up being right all that easily.

I can’t change the job/income situation and have to work towards complete acceptance, and I am trying. I know I’m a snob when it comes to this and part of that is the by-product of living in a wealthy area. Going backwards in income was never a welcome thought before now. I am truly unsure where this lands for me so we will have to see. In an early relationship, this has no bearing so I’m letting it go.

I hold out hope that I will become more physically attracted to Scott. I can’t force this so it’s another thing I’m letting go of. Sex has improved. Our sexual cadence is much, much slower than when I’m very attracted to a man and he doesn’t push me. I only hope he doesn’t feel like I’m not attracted to him. I don’t want him to feel this from me.

After the weekend away and my subsequent decision to give it a real shot with Scott, he came to spend 3 days at my home. We went to a winery one day and the next day we did a bunch of nothing together. He was thrilled I watched football with him and asked a lot of questions about his favorite team (until I fell asleep on his chest!). I made him breakfast and lunch and I think he enjoyed being waited on a little. I don’t think he’s gotten very much positive attention in his life and I get the impression he’s always been the giver. I like to be able to do these small acts of service for Scott because I know how much he appreciates them. We had a fabulous dinner out over the weekend and there’s no shortage of laughter and easy flowing conversation. It really does feel natural with no pretense.

So that’s two long weekends in a month in which things consistently improve. I’d say that’s a win in itself. We text often every day now and talk most nights. A relationship is beginning to form in its own way.

New things I’ve begun to notice and I’m trying to work through:

If I like it, he wants to like it right away too. While this is great, I want someone who maintains their own identity. I decided to run a half marathon and he immediately chose to run it with me. I like a certain type of music and he wants to listen to it all the time with me. I like wine and he will drink it with me. I like shellfish and he will eat it with me. None of this is bad, I just don’t want him morphing into what he thinks is the perfect man for me simply to attract me.

He compliments me constantly. Nothing is ever wrong with me (except he thinks I’m snobby too, who wouldn’t). Again, not sure what I think about this. Of course I want to be all the things to him but it falls flat when every word out of his mouth is how beautiful and special and amazing I am. Again, not really a negative but for some reason it’s overkill?

The last piece: I notice he doesn’t really ask me a lot of open ended questions. He is very in tune to me and pays attention, but he doesn’t seem to try and get to know the way my mind works. Rather, he goes for the outward things like my favorite food, wine, exercise (he joined Peloton because of me) or music. These things he nails because he watches me closely. Tony dug around. He asked about my family, my past, my education, why I liked some things and not others, what I dreamed of, what my sorrows were. Scott seems to be focused on how to please me. He often notes that I ask him a lot of questions and some of them make him uncomfortable to be so vulnerable but he likes opening up to me. But he doesn’t really come up with his own questions. I’m not sure how much this matters right now, we all move at different speeds and Tony’s matched mine exactly in that respect. I think Scott wants to to reveal myself in my own time without his prompting. This has actually made me realize I may not tell him everything (I can actually thanks George for that lesson in fact). Maybe he doesn’t need to buy the cow just to get the milk. I’m not exactly sure what I think of this but there’s a part of me that’s glad he isn’t probing further since I’m not ready to be that far into relationship with him when I’m still tenuous in some respects.

Maybe my reticence is because I may still have walls up. Maybe it’s self-sabotage. I don’t really know. He wants to please me so badly it’s amazing to me, but maybe I don’t want to feel like I’m continuously taking advantage of his crush on me. I don’t have the answers to these questions, but I do feel a certain amount of reticence for an unclear reason.

Next week I will head down to his house for almost a week. With the distance between us (and the cost that brings) it forces longer visits and I think it’s worth seeing Scott in his own surroundings. He’s super excited I offered to come to him and wants me to meet his adult daughter. I have no doubt we will have a great time and I’m looking forward to having more continuous time with him. We will have a mini weekend getaway as well as we’ve decided to run our half marathon around the National Mall in DC. That was his idea and, as hard as it is to impress me, he really doesn’t fall short in this area.

Maybe my lesson is about finding balance. I’m certain there is a lesson in here with Scott. I’ve got a good thing I intend to let run it’s natural course with no preconceived notion of duration or “what’s next.” I’m opening myself up to this pretty great guy and seeing where it takes me.

So there it is, the whole Scott story in a big word dump.

I don’t know what’s next but I can tell you I’m looking forward to seeing him and spending an extended amount of time with him next week and I’m happy to take it slowly for once.

I am so confused….. (Part 2)

For the first time, since Tony, I was so confused about how to move forward. The difference now is that I’m not in love with Scott so the overwhelming emotional component is missing – so why am I so conflicted when my heart isn’t involved?

I finally realized through my reading on intuition that it was because my gut was involved when I didn’t even know it. The battle I had been waging was between my gut and my head, rather than my heart and my head. That’s interesting.

While I’ve detailed so many of his good qualities, there are several that have concerned me from the beginning. I know before I wrote this how shallow some of them sound and all I can say is this: I was raised very differently from Scott, we did not start from the same place and life experiences shape us.

Scott was born into a poor family in the Midwest, the actual backwoods. His family kicked him out in 7th grade and he had to stop school and earn a living. He was married by the time he was 18 and she was pregnant. Knowing he needed to make a change and support his new family, he joined the service for 4 years. Some time after service, he realized he needed more than selling cars or working in warehouses so he went to school and obtained his Bachelors degree. Some time after that he began working for the government and subsequently earned two masters degrees, one being from Columbia. He was in a long and failing marriage that produced two daughters. One who he is very close to and one who doesn’t speak to him. Post his divorce he became involved with a married woman for 3 years. That relationship ended entirely about 6 months before we met. Like me, they were always on and off and he dated during the years of the affair. He owns a home and is stable financially. He has come a long, long way from an uneducated kid from the sticks.

I was raised with everything given to me and my education was expected as well as paid for by my parents. While I made missteps educationally, I fell into management and had pursued a career that was lucrative until 2018. You know I’m spoiled and have been around middle class money for my entire life. I never really struggled to put food on the table the way Scott did. My arguments with my x revolved around how much money I should spend on vacation. I am not frugal and always believed I would earn a pretty decent living. I bought my home post divorce and was going to be able to contribute significantly to my kids college educations. Once I left my role in 2018 and had surgery I never regained my financial or career footing. However, my expectation of my own income and financial situation never faltered, not until very recently. I admire ambition and career success that nets a large financial gain. Since my divorce, that has always been a significant attraction because my x was willing to allow me to bear the financial burden of the lifestyle we were living and I never wanted to feel that way again. Money and earning potential had become much more important to me post divorce because of my experiences during marriage. It actually became a dating qualification. I had grown used to some luxuries that I provided to myself and I didn’t want to give them up. I had fought too hard for status.

Scott works for the government and, as everyone knows, the government caps salaries no matter how good (or bad) you are at your role. Because of this, the government employees also are known to rest on their laurels and do the minimum required work once they pass a certain time in the job. The private sector would fire incompetent or lazy employees, while the public sector tolerates this for some reason and makes it very, very hard to fire someone. The stability associated with a government job as well as lack of incentive breeds a sort of laziness that’s commonly known. This is NOT Scott by any means, I am just trying to set the stage. Government employees also work very standard hours. You put in your 40 hours and not a minute more because there is no incentive to do so. This also creates a fabulous work life balance because the hours are dependable and stable. As long as the employee is willing to sacrifice earning potential, a government role isn’t a bad one to have and why most people never leave them despite their apathy towards their jobs.

Of course I am over generalizing as well as stereotyping. But, based on my experiences, this sort of apathy does exists and breeds a sense of arrogance in government employees. They know they can’t get fired, they know they only need to put in the minimum effort and once they reach the ceilings of their roles, they become big fish in small ponds and that creates a whole other sense of bravado. And this IS Scott. He’s at the top of his game and will likely be in this salary pool and role for quite some time until his boss leaves. He has no desire to go after more because he likes his 40 hours a week and is satisfied with his salary. He has come from nothing so where when is today is a great achievement and it’s ENOUGH for Scott.

But Madeline is wayyyyy more judgmental coming from corporate America and the private sector. Where the harder your work the better potential for financial gain. Where hours and work/life balance are irrelevant. Where you get bonuses, perks and promotions that you and everyone around you equate with success. Where you never assume you are safe or stable so you work harder in the hope it offers some protection when the layoffs come.

With those explanations, the divide between Scott and I becomes evident. He is a big fish in a small pond and definitely has an arrogance and bravado because of it. He also has a lot of time at work to chatter and gossip (I tell him he’s a wash woman and he admits to it). My experience as a leader has taught me not to gossip at work or even be perceived as a friend to all my employees. Scott says the government doesn’t have barriers like this – everyone is friendly with everyone because some people never change level but are age peers. Scott is satisfied with “enough”. The biggest criticism from my marriage and even my children is that it’s “never enough” for me. And that’s true.

I perceive it like this, if Scott is as good as he brags to be (another quality I do not like at all) then why doesn’t he leave and go make double or triple the money he claims he can make in the private sector? He says it’s because he doesn’t want to work any harder – he did it enough when he was young and he’s satisfied with what he’s accomplished. I thumb my nose at this since he’s only 46. I feel he’s too young to be so complacent.

But, that me. He’s happy. He’s satisfied with what he has and what he’s achieved. My fear is that my judgement, which has always existed (it’s not new, I’ve always felt this about people) is never going to go away and I may ultimately resent him the way I resented my x for never wanting “more”. I do feel he should be proud for what he’s achieved from where he started, but I don’t feel a man should be done at such a young age.

That’s the worst of my snobbiness out of the way. It covers almost all the qualities I dislike about Scott: lack of drive or ambition, arrogance/bravado (big fish in a small pond), gossip, braggart and the stereotype of a government job personality.

Unfortunately, there are other concerns.

I am not especially attracted to Scott. I thought he might grow on me but he isn’t. He’s not ugly by any stretch of the imagination and he’s very fit and pretty rock solid. He even has most of his hair! He is a bit short for my taste but still taller than me so I’m trying to let that one go. It’s just his overall appearance isn’t “doing it” for me. Combine this with ok sexual chemistry (not horrible but definitely not great) and I’m worried we have a toxic combination. I don’t find myself wanting to call him handsome or wanting to explore his body. Sex has improved but he has already told me I’m the best sex he’s ever had. He has been patient to learn what I like or don’t because sex in the beginning was close to bad. I’ve had some seriously amazing sexual partners – so should I be worried? My older friends tell me to forget about this. If sex is good enough I should be fine. We are getting older not younger. He never pressures me sexually but he really isn’t intuitive. He fumbles more than I would like for someone who claims to have had many partners. I hate being the leader because it leaves me with no desire. This one combined with the job situation worries me.

We come from different classes. Should this matter in this day and age? I didn’t think so exactly but I can see it pretty clearly with Scott. Being raised in a city or suburb of a city versus the middle of the country just creates a whole different person. Can you change that? Probably. He surprises me with some things like understanding some fashion brands but then there are other things that I just don’t get. Like shooting squirrels and throwing them in the grill. I’m unsure which divides can be crossed and which don’t matter. He’s also just lacking that “cool-factor” because of this. Again, not sure how much it matters except that sometimes he really does come across as a hick and I feel a little embarrassed. Luckily he has never done this in public, only in private.

Scott can also irritate me pretty quickly. He often starts stories in his head and then finishes them out loud, leaving me to decipher what he’s talking about and me getting frustrated with an unclear story. For someone as smart as he is, it’s all book smart. He definitely has trouble getting his thoughts out of his head in a cohesive manner.

His humour is a bit low brow for me. Reminds me of my x but I can manage this. He does come from the middle of the country.

So it’s sort of like 3 big negative buckets:

The job/ambition and the type of behavior a government job has created in him

Attraction

Class

I thought I was getting this out in 2 posts and clearly I can’t. So the rest has to wait for part 3!

I am so confused….. (Part 1)

Let me get out the dilemma very quickly…..I began talking again to Scott who I determined “wasn’t for me” for good reasons. I know this man REALLY likes me. The talking continued, then we met again for a night, then we ultimately spent a weekend together and had sex. You can read out my initial meeting with Scott here.

And now I’m stumped. I’m so confused.

I don’t know how to write this post exactly but I need a word vomit right about now. I have so much stress in my life right now that I have a persistent and near-debilitating headache every day. I’m hoping this will remove at least one stressor.

Do I write a pro and con list? Do I approach this like I would a business problem and remain removed and analytical about it?

My greatest fear is that my predetermined notion of the man I’ve been searching for is not allowing me to give a perfectly good man a chance. I’m also worried I am leading him on if I continue to see him when I already have concerns over certain personality traits.

Recently I was doing some reading on gut feelings and intuition and a little light bulb went off and I acknowledged something. Scott removes a lot of anxiety from me and I don’t know how. I feel safe and loved with him. I’m calm, happy and content. I don’t feel any of the traditional dating pressures to behave a certain way or look a certain way – I am totally myself with him. I believe a lot of this is because I didn’t really care what he thought of me because I didn’t see a relationship with him working out longer term.

Intuition is based on understanding something instinctively without the need for conscious reasoning. Soon after I met Scott, I fell into analysis paralysis regarding the possibility of relationship with him. I thought of so many reasons he wasn’t right for me while ignoring, perhaps, some less obvious natural feelings. It didn’t help that we only had a few dates before Covid quarantine started and the relationship became fully virtual, and there was no physical interaction.

I’m going to try and lay these out to have a bit of a brain dump. I suppose its a pro/con list in a way.

Scott has all the best qualities of what I loved in Tony. Many are even better. With Scott things have been easy and comfortable. He has seen my not so pretty side because, early on, I had determined he wasn’t for me and didn’t care how I presented myself to him or what he thought. We laugh so much over the dumbest things. We can talk for hours about nothing. He is beyond thoughtful. He would do anything for me. He is always focused on me and I can feel how much he cares. Anything I like he is willing to learn about. He wants to please me. He worries about me. He loves my body despite the scars and age. He’s smart. He has very little, if any, pretense. All of these traits were obvious right from the start and kept me wanting to give him a try.

My initial concern about the early relationship was that the combination of these qualities makes me feel amazing, but I wasn’t sure that I had feelings for the person making me feel good about myself. In other words, I liked how Scott made me feel, but I’m not sure I really liked Scott as a person. After about 6 weeks of quarantine it became apparent to me that I didn’t really like Scott well enough to continue speaking to him – and I knew he really wanted more from me. I couldn’t continue to be unfair to him.

So, I broke it off and I felt relief when I did, so I know that was the right decision at the time.

At some point during my surgery he reached out again and we began speaking. Slowly at first, with an up-front conversation in which I was very clear I could not offer him anything beyond friendship. I am not obtuse enough to think that he didn’t believe there was still a chance of more with me, but I convinced myself he’s a big boy and it was his choice to play with fire.

One weekend as we were chatting, and I wasn’t feeling so great about myself and my situation, he said “I will be right there as soon as you ask” and I said “ok”. This is no small ask – he lives 5 hours south of me. But, he jumped in his car and he came to me. We spent an evening laughing and having fun and he slept in my bed with me. He tried once to kiss me and I insisted that couldn’t happen. We remained on opposite sides of the bed for the evening and had a lovely Sunday before he left to return home.

A couple weeks after that, I had to drop my son off at school in his state. I was further west of where he lived, but he wanted to come meet me before I headed home. He came over once I finished with my son and we spent another evening together. Once again, a fun and laughter filled evening, sleeping in the same bed. Absolutely nothing happened this time except that he held my hand everywhere we went.

After this trip, communication increased and once again became daily by text. I was talking about my birthday and complaining about not having any vacation this year. He suggested we do something together and I agreed to spend a weekend with him, away.

The short version of the weekend was we had an absolutely amazing time. We acted like a couple the first two days, despite the fact we were not having any physical interaction beyond hand holding. But, by Sunday morning something changed for me and I initiated sex. When we were done, he said he was so happy because he wanted to be able to have sex with me “just once more” and if it never happened again he would be content because #lifegoals. The day we spent together Sunday was different from the preceding two days, now we were behaving like a couple and I was enjoying it. Where he had previously gotten on my nerves after about 18 hours together, here we were on day 3 and I didn’t want it to end. I was feeling something very different towards Scott, and it truly surprised me.

After we arrived home and parted, the analysis paralysis began. All the reasons I didn’t want to continue with Scott before were still there – they hadn’t changed. But a new feeling had surfaced, one I haven’t felt since I met Tony: contentment. I felt content, at ease, satisfied and low key happy with the time I spent with Scott.

I began an agonizing two weeks of torturing myself on if I should continue with him or not. I did not want to hurt this man twice. He is so good, so kind and so into me that it would be horribly unfair. My headaches grew so bad by this point I needed migraine meds. I was unfocused and becoming increasingly unhappy. Scott isn’t to blame for any of that – my life is in a shambles for some time now and adding the relationship conflict on top of being without a job for a year was beginning to wear me down and create a permanent anxiety I was having trouble ignoring.

The crux of the conflict with Scott is this: I finally met a man who fills almost all of my emotional bucket (maybe actually all of it) and creates some unidentifiable feeling within me, yet there are characteristics and circumstances I am so hung up on that I can’t seem to get past them – and they are not exactly changeable characteristics or circumstances. Even if they were changeable, I’m pretty sure Scott isn’t interested in changing them. We have a disparate view on one very important quality for me: career and ambition.

Where do I go from here?

(Well, we go to part 2 for now lol)

Tentative Maturity

My brain knows (most times) what’s right and when my brain isn’t paying attention my gut generally steps in. I don’t always listen but I have been making a very concerted effort since my breakdown to try my best. I show up for myself most days.

That probably sounds like I did something dumb. I actually didn’t. I’m just feeling a bit (well, maybe a lot more than a bit) melancholy. Dropped my first born off to college, I don’t have a partner and I’m still out of work. The sense of loss or failure is looming large and I’m working really hard to keep myself together.

I met a man online named Peter. He came to my home for drinks – it’s so hard to go out anywhere and I don’t really want to keep inviting men here, but there’s no option for a casual drink anymore. My back deck suits just fine but I hate that the kids know I have company. Going to a park feels really awkward to me and I won’t go to someone else’s home. I think I vet them well enough before they come here but I suppose one never knows.

Peter was a nice guy but I struggled with the laughter again. He looked like his photos but didn’t, hard to explain. He wasn’t unattractive but I found him less appealing in person. I am somewhat critical about how people dress because of my industry, but it’s no dealbreaker. He was just dressed too young for his age. He talked too much about himself and his business. He asked a question and before I could form a complete sentence was interjecting whatever he wanted to tell me about himself. He literally pulled his cock out of his pants as a joke that just wasn’t funny. I didn’t look. I looked him right in the eye and told him he was dumb. He felt chastised but that wasn’t my goal – what is it about me that makes EVERY man lead with sex? What vibe am I giving off and how the he’ll do I stop? The date wasn’t a complete loss, but I wasn’t really feeling great about it.

I should have cut it off immediately after the first date but I know I didn’t because I’m lonely and thought to myself I should give him a second chance. He was good about communicating every day but I began to get frustrated with the same questions. I think he must have asked me if I liked salmon no less than 6 times (I don’t). It felt like a boring Groundhog Day in most every conversation. He is a part time basketball coach so at one point during the last conversation I asked him if he liked basketball. 😂🙄. I was entertaining myself again – I knew it was time to just call it a day. We were due to have our second date this week and he was going to make me dinner (you can guess what he wanted to make).

I really am not sure if this guy was a space cadet or really disinterested. I don’t know, nor do I care. But he didn’t pay attention and he certainly didn’t ask much about me beyond “how are you” or “what are you doing” type of questions. I know this is how you gauge a mans intent. They always show you who they are at some point early on. When I sent the text today to politely decline dinner and moving forward, he replied that he was caught off guard. Probably because he was too focused on his attraction to me and not paying any attention to our actual interaction. Or maybe he just wanted to sleep with me. Doesn’t matter.

I still had a little trouble writing that text to let go in favor of having some company, any company. I knew I should have written it last week but getting my kid ready for college drop off consumed my time and thoughts. I still feel loss today. I suppose the loss is ambiguous- I am not mourning the loss of Peter – just the loss of my child to his adult life and the hope of relationship once again. The general loss of my life as it was pre 2018.

I still can’t help myself to think of each new match as future potential. I don’t know if this helps or harms the dates. I don’t believe I come across as needy, unhappy or depressed but I’m starting to feel the weight of frustration. My x has now been in a relationship for 2 years and the kids have dinner with them once in a while. I suppose this bothers me as well on some level and I think whenever a long term partner gets into another relationship there is some adjustment period. I did have a good laugh this weekend when my son told me that his grandmother no longer thinks of me as the devil and says she preferred me. More like the devil you know with my x-MIL.

The man I started to see before Covid, Scott, lives in the same state as my sons college. We have established a tentative friendship. I know he would like more, he knows I know, but he is willing to be friends.

Then there’s Mike. Why? He never fails to make my heart flutter and I don’t think he’s truly contrived, but I sort of don’t get why he does what he does. On the nights we spent together (a year ago now) one song seemed to be on repeat and he would sing it to me. It was one of the things I found so endearing. He must have been home alone and the video came on and he sent me a clip and said “every time I hear this I think of you”. Why? Why? Why can’t he just date me? Dumbass me responds with “lets have drinks on the deck”. No response. Of course. Delete yet again.

Tony is back stalking my IG. Any attempt at blocking him results in follows from made up names. It does cause “some” kind of feeling but the closest I can identify is sadness. I have no desire to reach out. If he wants to stalk, or if it’s his wife, then so be it. I’m really done now. I know it took 2 years and nearly killing myself but I can say that I am no longer in love with Tony.

I do feel I am making good choices – part of that is the choices are sincerely limited – there are not any good matches coming up for any of my friends. Part of that is the realization that I would rather be alone than with someone I am not ultimately compatible with.

But depression is seeping in much faster than I feel I can control. And this worries me….will I be able to manage the depression without becoming reckless again?

Breaking Quarantine Virginity

I think it was a big deal to decide to have the first post-quarantine kiss with Darren, but I felt pretty confident he was safe. We had spent quite a bit of time talking about where we had been, what we had done and what we were doing to remain safe.

I was probably less cautious the second time with Rich. I certainly didn’t pay enough attention to small alarm bells going off because I was too focused on the “what’s next” instead of the “right now”. That is the first time I thought forward in an effort to remove some of the things I didn’t like about Rich immediately. I allowed myself to ignore some warning signals in favor of moving forward.

It was a mistake that left me baffled to be honest.

Rich lived about 2.5 hours north of me. His profile was equal parts interesting, funny and appealing. One photo (which is always the photo that is MOST accurate) wasn’t particularly attractive to me, but all the others showed a handsome, fit and active man who was 52 years old.

Rather than tell every detail I thought I would split the post into three parts: what happened, what I ignored, and what I was thinking along the way that caused me to ignore the things I ignored!

We met on Bumble in early July and text, talk and video chat until meeting in person about the 3rd week of July. Conversation started easily and at a steady but not overdone pace but really heated up to much more protracted and intense conversation the week leading up to our meeting. He made no qualms about driving down to see me and knowing he was turning around to head home the same day. Initially we planned lunch but it was a 100° day and stormy so the humidity was deadly. I invited him to my home. We enjoyed conversation and moved to kissing. It really heated up and we ended up having sex a few times. It wasn’t great but it wasn’t bad either. He didn’t spend the night and we made immediate plans to see one another again. He would drive back down and spend the night. This entire time, Rich made it immensely clear how he was attracted to me and why. He seemed very excited and hopeful about our connection. He felt very open and genuine to me. I never doubted he was really, really into me. I told him about it surgery before sex and he wasn’t fussed with my new scars. The second time he came we went it to a really lovely and fun dinner and then continued the fun at home. The sex wasn’t much better than the first time, but again, ok. In the morning, we shared coffee on the deck before he left. Conversation remained normal for a few days and then turned to intermittent text with no discussion of a phone call or when we would see one another. He continued to indicate his interest in text but the comments seemed to be contrived now. There were no more phone calls. There were no requests to see me again. After a couple days of this, assuming he was just busy with work, I asked when I would see him again and made a proposal. We had one phone call which didn’t go very well, he just wasn’t engaged and called at a bad time for me. Eventually his text became less and less over the next few days. By Sunday Aug 2, one month after we started speaking and 2 weeks since we first met, he sent one strange text in the morning which I didn’t reply to and I’ve not heard from him since.

That’s the summary of what happened. Ghosted in only one months time for no apparent reason.

Here’s what I ignored – and when I told my friends all of this they looked at me like I had two heads for ignoring so much:

He looked older than 52 in his profile: he was 58. How I figured it out: I couldn’t reconcile his timeline of marriage, kids ages and subsequent relationships. So I asked him directly. Ok, everyone lies about age but 6 years is A LOT. The lie: “is my age wrong?” he claims he didn’t know his age was incorrect on his profile. Oh, come on.

He said he was married once. He wasn’t, he was married twice. How I found out: a friend found an article about him and within the article it indicated he was married with 4 kids while I knew he only had 3 (haven’t met anyone yet who lies about the # of kids they have!). When I asked about how the reporter got it wrong, he then told me he was married for a short time and she had a daughter. The lie: “I was only married for a year or so and it doesn’t really count. No one wants to know a man is married twice.”

He realized we were no longer connected on Bumble. In all honesty, I meant to pause the app. I got distracted by a new feature and deleted all my matches and conversations, including his. How I found out: he asked, supposedly days after he saw I wasn’t there. The lie: “I went into the app for your photos while I was driving down to see you for our second date”. You go into the app for one reason after 3 weeks of constant communication, to check your messages from your matches. He had received plenty of photos of me by that point.

One night he disappeared the entire evening until the morning. We had been chatting normally until 4pm. I sent 3 text after that which went green (iMessages are blue) and I knew he wasn’t out of range. I called and it went to VM. The lie: “I got a new phone and it took all night to transfer the data and phone # over.” How many of you have gotten new phones where it took a whole afternoon/night to transfer over? Never. I need to add why this is so suspicious, it was the day before he was due to come down and not hearing from him for 20+hours (because he didn’t text first thing in the am, it was after noon) made me assume he ghosted me. The funny thing here is he said “I would never ghost you, you must know that’s not my style!” Funny that.

Then there are the things that really didn’t sit well with me:

On his first trip down I realized too late I never have him my address and sent it over. He said he had already googled me and found it. This sort of bothered me but I know we all google each other. It just felt weird that he never asked.

Every significant relationship (he had 3 other than his two marriages) he ended because the woman couldn’t make the decision to move it forward to more (or marriage) after living with them. He claimed he tried everything he could so it wasn’t his fault. At first I felt he had a lot of healthy relationship experience but I began to look at this differently as time went on. One was a narcissist, one just didn’t want to leave her town and hour away and he didn’t want to move to that town, another one was hyper focused on work and wouldn’t talk about the future, and another got pregnant without his consent. Then I found out some doozies: his daughter was the product of the woman who wanted more and he didn’t yet he kept having unprotected sex with her and eventually she got pregnant. She was also extremely volatile and always threatening him and taking away his child. His first divorce was so contentious that he was arrested multiple times. The layers of complexity were brushed away as unimportant details of past relationships.

The first 2/3 weeks we spoke and video chat it was green text (indicating android phone) and Bumble video chat. One time he said let’s face time and I laughed and said he couldn’t do that with an android phone. He then admitted he was using a burner number the entire time and gave me his real phone #. He claimed he had a few women just keep trying to contact him so this felt better to protect his information. The lie: you can google him and his real phone # comes up. I just didn’t catch this until after this happened. He has a very public company in real estate. This is the first and only time in 6 years I’ve met a man using a burner number.

He said he dated 175 women before he found his last relationship that last 4 years. 175 in a year! I looked back and in my best year I dated 35 men. He was looking for his formula. This is why he was still checking his Bumble matches and why he disappeared at the same time every day.

The morning we woke he was very, very ready to have sex and made no moves to do so. Eventually I asked and he declined. I made a silly comment about rejection and got out of bed to start the coffee. Later he told me he didn’t reject me and it had nothing to do with me. That he was trying to change the way he approached dating and not get so hung up on the sex because it made him fall faster and he was already falling for me. I wanted to believe this but it didn’t feel right. Rejection is rejection and we had already had sex multiple times the day before. The way he said the words sounded like a script from a book if that makes sense. Don’t let her think you’re gaslighting her.

He had already gone on multiple first dates during Covid. This should have given me more pause than it did but he claimed there was no connection and therefore no kissing or sex.

He claimed every relationship he ever started had began with first date sex. He spoke about his sex drive often once we addressed the conversation yet he had a little trouble in the beginning. He said he hadn’t had sex in a year after the last breakup and was really waiting to meet the right person to start his next relationship before having sex. If these were “lines” to convince me to sleep with him they had no impact on my decision to be a ho or not! When I type them out they sound like lines. Lol.

Wasn’t all of those small white lies enough to equate to one big red flag that said stop? Nope. Here’s why not:

He had a lot of attractive qualities that I liked for the long run. In particular: he was very fit and active, he liked to socialize like I did, he seemed like a good Dad, he seemed to have a good track record with relationship, he was interested in me and made it known by his communication (that’s a big one for me), he was single, clever, an entrepreneur, and looking for a LTR.

I was never especially attracted to him but when I looked at him I thought “I might grow to like his appearance more.” His body was fucking fine for a 58 year old man, better than most men I’ve been with. Like, really really fine. Damn. Lol. Anyway, I neglected to see I was dating myself with laughter – he wasn’t particularly funny and I carried most conversations once he learned most of what he wanted to know about me. This was suddenly and glaringly obvious on our last phone call.

I sort of knew from the moment we didn’t have morning sex that things were heading downhill. He didn’t let on the first few days, but it soon became apparent. Since I’m trying to listen more and talk less, I caught on to his change in conversational style pretty quickly.

In hindsight I realize Rich was much more contrived than I gave him credit for. I didn’t put stock into his many comments about me being the perfect match for him and his excitement in connecting with me. (See, growth here people!). I know it’s because I never got the butterflies with him – but he said all the right things and stuff I normally would kill to hear.

The strangest thing of all. The last text he sent was “early day for you running.” At 7am on a Sunday. I hadn’t spoken about waking early to run and I double checked that I never posted anything like on social media. At first it stopped me in my tracks like how could he have known. I never answered that text and he hasn’t text since.

So much for never ghosting next, Rich. Cause you’re not that type.

I was a little butt hurt the first week, sure. Mostly because it was pretty drastic that he just stopped texting entirely. Then I just reminded myself that when a man is interested they pursue. They ALWAYS pursue. I recall when I first started dating that I just didn’t believe this. This is a fucking fact.

I do wonder why I am having so much rejection and don’t date anyone longer than a month and generally the ones I choose to sleep with are the ones who ghost me. This fucks with my head for sure. In this case I look back and don’t see anything I did wrong. I’m certain Rich was playing a broad field and lying, I just ignored obvious signs.

At least, that’s what I tell myself.

The Big Quarantine Lesson

Before anyone else says it, let me say it first – I should have learned this sooner and saved myself a whole lot of heartbreak.

I wrote that George and I played a question and answer game that forced deep conversation. It opened doors that normally would never be opened as quickly in any relationship. It exposed raw thoughts and feelings. It highlighted both the individual and couple strengths and weaknesses. It is not a game to be played with anyone you are no serious about having a relationship with.

George was serious. I was not. I was pretty sure George was going to pursue and I was going to flirt. I was initially in the position of power here.

Until the game highlighted things about George that reminded me why I loved Tony. That fucking game. But I can’t just blame the game, it’s the way I played it. That was my big mistake.

Now, it doesn’t matter whether or not I played the game right or wrong in terms of having a dating relationship with George. I know I played it wrong for having a dating relationship with ANYONE. And that’s where the life lesson was found.

There were multiple categories and questions within each category. Some were harmless, some serious, some sexy and some flirty. But some were deep, like really deep getting to know you stuff.

The questions and answers themselves don’t really matter. Nor does it matter what George and I said to one another or how it ended between us (spoiler alert: covid made the decision, not us). What matters was when George said this can’t go on and I realized how I was going to feel about that (because we had created a false sense of deep intimacy) I had to take a good hard look at myself and understand why I was feeling so anxious and depressed over a man I didn’t initially even want (I can still stare at his photo and wonder if I would be attracted and find myself guessing not) and had never met. I lie in bed for a good two days really feeling sorry for myself. Quarantine did not help this overwhelming sense of depression and rejection. I really took this rejection harder than I should have.

George did say if it wasn’t for covid and we had an opportunity to meet, he would want to start talking again with the hopes of potentially building something. On the other hand, he thinks he’s too needy for a long distance relationship so chances are it’s not the right relationship for him. He never said he didn’t want me, didn’t like me – none of that. I can say, in hindsight, that we are not compatible for many reasons which led to him needing to take a break from “us” anyway. He did the right thing I just had a hard time acknowledging it at the time. My vision has become much more clear with introspection.

So here’s what I did wrong when I played the game – I threw out careless answers to shock because I didn’t think I would ever be interested in George. For instance: what is something you would never do again? My answer: go to a swingers club.

Another one: is it ok to have sex on the first date? Me: Abso-fucking-lutely!!

Shocker. George is basically a prude. 😳😂 He could never quite get past those two answers. He did not like sexual banter in general and I had to pull back on this because it’s a go to for me when I don’t care where the conversation will lead.

Does it matter that I shocked George in particular? Nah. This is about what I learned for my long game. When I thought about what I did – I realized I need to keep my mouth shut. I do not need to shock anyone. I don’t even need to tell anyone any of my personal business so quickly. Especially sexual. I play all my cards early on. I run my mouth. I over-share. I want the man to know everything right away. Let’s jump into the deep end! That has to stop. Like immediately.

Even, perhaps, maybe never share some of the things I’ve done. Do we really need to tell the intimate details of our past? Is that a requirement? Jury’s out on this because I like the transparency but maybe it is the right move.

Ok, lesson one. Learned.

George is very polite. He doesn’t argue or disparage. He tries to understand and appreciate differences in people. He values shared activities with his partner. He values compatibility that isn’t solely based on that white hot chemistry. So much so he won’t have sex until the 3rd date night matter what.

How the game played out here – the question was “what is a bucket list item to do with your partner?” George’s answer was to visit every national park. My immediate reaction: I’m not doing that. Why? Why would I have to stomp on his bucket list item with my own opinion? Because I didn’t think I cared about a relationship with him, that’s why. But what it taught me is that I need to keep my mouth shut. Sure, that’s not up my alley. But a better reply would have been: tell me what interests you about doing that? It opens an opportunity to learn more about the person. I just shut him down and disappointed him. And I didn’t do it just once, I did it a few times with a few things. I think in my head I’m trying to be honest and open about my dislikes, but I realize I can accomplish the same by taking a different path. I could add it’s not something that ever interested me before so the jury would be out on if I would enjoy it or not but I was open to new experiences. Perhaps it doesn’t apply to everything, but it can certainly apply to many.

I also learned, through conversation related to the game questions, the types of activities he likes to do with a partner and I was very attracted to this. I realized it’s been a very, very long time since I’ve done anything shared with a man. I’ve literally had one active date ever since divorce. I don’t think my opinion has changed that a first date should not be a shared activity, I prefer a drink, but it made me realize how much I wanted someone to share activity with. When I thought about the men I’ve dated, it was a quality I had long been attracted to and not acted upon for one reason or the other. It made me realize that date 2 should be a shared activity. Of course quarantine compounds the feeling of needing to get out and be active.

Lesson two: learned.

George is by no means some perfect man I let slip through my fingers. He’s set in many of his own ways and was looking for me to fit that mold and ignoring some of the disparity in favor of the things he liked about me. But he is a kind man who was willing to talk about his feelings and share his thoughts. I know for sure I appreciate this in a man. He is communicative and open. He is funny. He is really smart. A dad. He’s working hard to lose weight and be toned and fit and he’s doing a great job. He checked a lot of boxes (like almost every single one) but at the end of the day, he really isn’t my type. The game highlighted this as well and made me think to go back to my list of requirements and evaluate how I actually interpret them because “on paper” George did check the boxes. In actuality, maybe those boxes don’t define what’s truly compatible for me.

Lesson three is an activity for me: go back and think differently about my requirements and how they really impact if someone will be compatible for me or not.

Bottom line, I learned I need to go into dating a little less aggressively. No one needs to know all my darkest dirtiest secrets right away. And when I do choose to reveal them, it shouldn’t be in throw away comments, ever. I need to be more open about a potential partners likes until it actually happens – again, it doesn’t need to be solved right away in the first few weeks. When I think about how I’ve dated, I’ve put my best physical foot forward: I look good, I laugh, I’m smart, I’m sexual etc – but I don’t think I’m actually playing enough of the dating game by keeping my cards close to my chest until the time is right. I don’t mean to create a false impression of myself, just a less obvious one. I need to hold back more, give less, and be less invested. I have always been an all-in person, every time. That’s how I’ve gotten hurt so many times.

Before I had any in-person dates, I put these words into action. I looked for the right kind of connection and tried to focus less on immediate physical chemistry (at least from text and phone). I focused on the persons background, similarities, lifestyle and all the things that would make us compatible. I listened more. I asked more questions and I offered up a whole lot less about myself. I edited information about my past relationships, health and career – not lying l, just not giving up all the details right from the start. For my career, I learned to say “I have had an amazing and robust career and I’m looking forward to the job market opening back up for my next opportunity ” instead of diving into why I’m not working and how I feel about it because EVERYONE thinks they have the answer for how I should be recreating myself and chasing what’s next. For my past relationships I learned to say “Ive had two longer relationships which I valued but the details are best saved for in person conversation.” And, most importantly, I entirely avoid the sexual flirt and innuendo. If a man goes down that path with a gentle innuendo I can give a gentle one back, but don’t allow any lines to be crossed. I can tell almost immediately when this frustrates a man and it shows me where his mind and probably his intentions fall (however some are better at this game and you can’t always tell).

While George and I were not meant to be more than friends, that game and our interaction (and my mind being so quiet during quarantine) really opened my eyes for how I want to show up go forward. It’s time I grow up and realize I’m looking to play a long game here – and need to find a man who can do that with me.