Date 2 | Results: Partial Fail

I met Peter on Match and he was at the high end of my age range at 55 years old.  He had a very nice background and profile and we seemed to have more than enough in common to start a conversation.

He was chatty and well-spoken in text and we connected easily.

Then the red flags started, one at a time and far to obvious.  I should have stopped when the flags started popping up, but I was curious to meet him.  His job was fascinating and he was really engaging.  I figured, at least, he would be entertaining.

He started talking about his vacation after a particular work project had finished and we exchanged thoughts on places we wanted to visit on our bucket lists.  This was fun as we both liked travel and had a lot to discuss.    Soon after he began sending me photos of the location he choose and I “oohed and aahed” appropriately.  Then he said something along the lines that the vacation would be so much better if a romantic partner came along.  While I agreed, I didn’t actually engage.  He tried multiple times to pull me into a conversation about lounging by the pool and lingering mornings in bed and I simply skirted a full-on discussion that would lead to a sexual interpretation.

Then he began to talk about how we could meet in the city and explore hotels together.  While the conversation was fine because that was how we would meet if we should go further, I once again avoided any discussion of the luxury sheets on the bed or room service.

More than once I mentioned to him he had a once track mind and he would say “I meant watching TV together in bed, silly”  He certainly wasn’t aggressive in his commentary or too pushy, but the undercurrent was there and I wasn’t engaging.  It did eventually begin to annoy me that he couldn’t seem to get off the topic and on to something worth discussing.

We were due to meet Friday after work and I had to cancel due to weather conditions.  I actually got the hint he might be mad that I threw a wrench into his plans.  When he said he was disappointed and then I didn’t hear from him for several hours, I just let sleeping dogs lie.  Eventually he came back around with his flirty self and began to ask what my free nights were over the next week.

While the red flags were there, I could handle them and I figured the flirting would be fun if we hit it off.  He seemed ok, holding the sexy talk at bay.

But there was one big indicator I started to realize and by the time I met him in person it was full fledged verified…..he was so self-involved he could care less about me.  He didn’t ask me questions about anything unless they related to him.  Nothing about my children, my job, my friends, my marriage, my life, my interests, nothing.  Only about pop culture, vacation, hotels and restaurants.

In a last minute decision, we chose to meet for brunch on Sunday in the city.  I chose the place and we met.  It was bitter cold and I was bundled up in a heavy coat and thick clothing, far from sexy.  I figured it was a take-it-or-leave-it deal.  If he didn’t like an average weekend look, then so be it.

He didn’t like me the moment he saw me.  I never know exactly what disappoints these men to be honest.  I look exactly like my photos, but I am not a slender woman.  I’m full all around and perhaps that’s what disappoints them.  In any case, I got the message loud and clear, I can usually tell immediately.

Which is fine.  He was older than his photos, and his stated age.  His hands and neck were very crinkly and I would say he was closer to 60 than 55, if not older.  His face was quite handsome and his shoulders broad, so he made a regal appearance.  But, honestly, he just appeared too old for me.  While I realize I am going to be 50 later this year, I have found very few men who fall into the “younger” looking category and perhaps that’s why I prefer younger men.

I also knew exactly which points of our conversation turned him off.  This became a bit of a silly game for me during the date, to mention going to a Depeche Mode concert with my girls in Stockholm produced a look of disgust across his face – why in the world would I want to travel to another country to stand in a loud concert, especially an 80s band?  His fun meter and mine are clearly different.  I got the feeling he was into “I like to rest and relax with my woman” stage, where I am still all about “let’s go out and have fun!” in addition to the rest and relax.

I don’t think that type of behavior is necessarily related strictly to age, but based on my sampling, men around the 50+ age mark just tend to get “old” and that’s sincerely disappointing.

He also was a braggart and this really was something I couldn’t stand.  He dropped names and wanted to impress me.  While I found much of his job interesting, I am also in a field where I am exposed to certain celebrity – so it doesn’t phase me quite so much.  Nor do I brag about it.  I’ve worked for several famous people.  So what.  He bragged about his job, who he worked for, where he lived and how his son is smart enough to go to Cambridge (at 13 years old).  Enough was enough.  I ordered my third Prosecco cocktail at that point!

In any case, the brunch was lovely, we made nice conversation for 2 hours, then a peck on the cheek and goodbye.  His last words to me, after I thanked him for a lovely afternoon, were “Thanks for making the effort.”

Oh, and no complaints from him about picking up the check.

And so, on to the next.  Because the date itself was ok and I didn’t feel like it was a massive wasted of my time, I consider it a partial fail.

In hindsight, I wouldn’t waste time knowing the red flags too early are still red flags worth staying away from.   But, it was good to see that I can identify the things I don’t like in a conversation well-enough to stay away from them now.  In the past, I would be upset letting a man of his caliber get away, even though I knew he wasn’t right for me.

Now, I just don’t care.


Author: Madeline Harper

My journey through divorce and an emotional and sexual reawakening. Love, laughter, friendships, family and heartbreak included. And there is sex, lots of it, so close your eyes and turn the page if that's not for you! While I started this blog as an endeavor to journal my thoughts and feelings in an attempt to better understand myself, it has become an amazing platform from which I have met some of the most interesting and wonderful people in my life. My path is often crooked, but I hope you will share in the journey with me.

17 thoughts on “Date 2 | Results: Partial Fail”

  1. For all the reasons you mention, my upper limit age cut-off is 52… and sometimes I think even that is too old. Men in general don’t take care of themselves as well as women (so they don’t age as well) and most in their 50s have completely different interests than I do or are else too arrogant for me.

    Liked by 3 people

  2. I find it frustrating, and all too common, that many men seem to struggle with showing actual interest in their prospective dates life and interests. So many times I have engaged in conversations with men where they are totally comfortable answering questions about themselves but they ask nothing in return…the conversations generally go stale if I don’t keep asking about them…unless they manage to turn the conversation sexual..then they are great at participating! I now just give it a bit of a try to get to know the guy….but if he can’t show a bit of interest in me then forget it!

    Liked by 2 people

    1. Yes! Exactly that! I asked him many questions about his life, family, career and he was only interested in the things which he could brag about and never once asked about my life. I think it’s a sure sign when a prospective partner doesn’t ask anything about my children when (of course) they ultimately may have an impact on my dating life.

      Liked by 1 person

  3. I love that you call this only a partial failure. If you only had the narrow objective of finding a compelling prospect, then this would have been a failure. However, you see that you were able to put in practice skills to extricate yourself from further exposure to someone who isn’t worth your time, and you were able to do so without getting hurt, and that is indeed a gold-star kind of success. Congratulations!

    The age-fudging issue is timely for me. I wonder if anyone has any advice here for me? Shortly after the New Year, I started engaging with a new prospect on OkCupid. He says that he is in his late 40s, making him 5-6 years older than me, which is right at my theoretical cutoff. I’ve been guarded with this connection since the get-go for other reasons, like he is inconsistent in his communication (goes dark for a long time, then writes novel-length emails), and he hasn’t honored my request that he send me clearer photos (since the one he has on the profile is blurry). I like what he has to say in his long writings, but I have also learned the pitfalls of opening too much to someone on-line, as it compounds awkwardness if there is no chemistry at the meet-up. Anyway, I finally learned his full name, curiosity got the cat, and I googled him. Three separate data-mining websites returned his name and a birthdate that makes him 6 years older than stated on his profile. He has a unique name, so there can only be one of him.

    I feel a little bummed out by this discovery. Not only is mid-50’s out of my age-preference-range, but misrepresenting age by 6 years seems extremely deliberate. I’ve certainly seen my dating prospects narrow considerably in the 7 years that I have been off-and-on the market, so I can see why someone in their mid-50’s would be tempted to fudge their age younger, but 6 years is a big chunk of time. I wonder if he obscures his image to also hide his age?

    I can’t confront him on this since he doesn’t know I looked up his age, and it can be argued that I shouldn’t trust a data-mining website (one of those background check sites…) but its taken the wind out of my sails with communicating with him.

    Given the infrequency of our communications, we had yet to even talk about planning a meet-up. But, I feel like we’ve opened up to a level of intimacy in our communications that it would be awkward for me to just go silent. I don’t even know what I am asking for here. I guess that I am just bummed to have been misled like this. I am not so bummed to lose a prospect, but it was a waste of my time and my emotional energy.

    Liked by 1 person

    1. If I might comment on this….during my on-line dating days, I regularly discovered men in their 60’s lowering their age to…55. That seemed to be the magic #.

      As for your on-line pen pal, I think he’s just that. Not someone for the real world but a lovely friend for the virtual one. He’s not being 100% truthful about who he really is which means perhaps he has other secrets. Just keep him in the netherworld where he apparently prefers.


      1. Thank you, maggiemay. Yes, I think that I will keep him in that department, especially as there are a few other inconsistencies with this person (goes radio silent for a long time, then writes novel-length emails, also has yet to follow up with my request to please send current photos). The irony is that I am an open-relationship person, I work hard (and understand how hard the work is) to represent myself honestly, and there are few things in another person’s life that would shock me. The most shocking thing to me is when someone needs to lie. I had a long chapter in my relationship-history where I let myself slip down that slippery slope and I am burned out both by my behavior and the behaviors of others.

        Liked by 1 person

    2. Hi Nich – I am sorry I missed to comment on this sooner. The age thing bothers me. I am ok with lying by 1-2 years because these search engines are only as good as a date. I did it and kind of expect others to do it. But, at least have very recent photos, or list your correct age in the byline/profile part. For sure, I have learned that too much talk before a date is always a bad sign (just as too little). Find a comfortable amount of communication – I would say no more than 1-2 weeks – and then meet or stop talking. I did all of those things when I started dating and it’s very true what you learn from comments on the blog – keep it short and simple with prospects and learn what you need to from a phone call and in person. Unfortunately, people lie for all their own reasons….I know I look like I am 40 or maybe younger to some, but it still wouldn’t encourage me to lower my age by 5+ years. I was guilty about the 2 years! lol Good luck. I think you already know whats right!

      Liked by 1 person

  4. You did great!! You kept your dignity intact, you were yourself and didn’t try to twist yourself into something you aren’t for his benefit, you were aware of the red flags & didn’t dismiss them. Well done!!

    Any man who cannot keep up a 2-sided conversation is just a future disappointment in the making. As for the age, lower it to 53 – the majority of 55+ men fudge on their age in my experience.

    Consider him a successful experiment in culling out the losers!


  5. Looks like I made it to today right? Glad to hear that you are doing well and flourishing in your career. Do not return to Bennet please. I think you always go for affairs because they are so much about fantasy. In the intimacies of a real relationship, a man becomes so mundane and annoying. But there may be ways to push past that and have a nice love even with a normal man who’s not everything you want if you make a commitment to working with him. It’s not as exciting as a fantasy, but there’s a stability and comfort there that could be good. I see a lot of mirrors in you and your blog for myself, as I remember when we were newer to the dating scene and more naive, and how exciting it all was. I don’t think there is any guy that will ever get things exactly right for you and perhaps it’s better to adjust expectations and fine tune things with single men where you can actually work on your relationship. But I know, that’s what I always say right? 😉

    Liked by 1 person

    1. Bennett was less about fantasy than any other man I have met. It’s what I fell in love with – an opportunity to see what a real relationship would look like. He did give me a stability I didn’t have before.

      I’m not disagreeing with you that I need an unmarried man. Just that I really did see partner potential, long term partner potential, in him. I’m most sad about losing him as my friend now which wasn’t something I was expecting.

      Liked by 1 person

      1. It sucks to lose a friend in addition to the lover. Give yourself and Bennett some compassion and think of the realization ASV had; its impossible (and somewhat self-deceptive) to maintain a friendship with someone who you are in love with, who is in love with you, where you can’t reciprocate those feelings. Perhaps that friendship will be possible once the limerence totally fades, once the attachment that is borne of romantic longing fades, essentially, once you stop requiring something of Bennett that he is incapable of giving.

        Liked by 1 person

      2. Oh no, I know I cannot be friends with him, that’s hands down for me. I learned that lesson with Bobby. I only mean it sucks to lose my closest friend and advisor. He was good to me and good for me and provided me with a good balance.


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