Casual, Flirty and Fun

As it turned out, the Almost Date guy came through with his phone call and we agreed to meet last week.  Since he lives in San Fran I knew full-on this was simply a casual sex opportunity and I was ok with that.  Maybe that’s even why when he didn’t want to call I was so easy able to walk away from his nonsense.  No investment, it was meant to be light and fun and got all too serious when I asked to speak to him on the phone.

Turns out he was funny and sexy on the phone and I was looking forward to meeting him.  We could only coordinate one night and easily agreed on where to go and what to do.

I met him at his hotel, which is also a large and popular bar.  It’s old city glamour and really pretty and period authentic on the inside.  My girlfriend lives across the street from the hotel so I let her know I was on a first date there, just in case, and also pin dropped my location to my other girlfriends.  I wasn’t worried, it was a popular place in the daylight but I am starting to think more clearly about my own safety.

I thought I did all the right things, checked off my list, asked all the right questions.  But, he lied.

And, of course, I saw it the moment he walked towards me in the bar.

I had specifically asked if his photos were recent and had received a resounding “Yes” along with some dates/locations of each.  Here’s the catch, there were two really good photos of his face/upper body up close, then several photos at a distance (more like action/vacation type shots).  Turns out, even when you ask the right questions if you are not VERY specific, there is a way to lie around it if someone chooses to do so.

The close up photos were at least 5+ years old and 25 pounds thinner.

Why do people think their brilliant personalities will usurp the fact that they had to lie about their physical attributes to get a date?

It’s a hell of a lot less about how he looked – he was still a pretty handsome man for 48 years old.  He was 6’2″ tall and had a gorgeous head of thick, wavy, black hair.  He had two-day old scruff on his face that was salt and pepper and just right.  He was overweight and had a belly, but that generally doesn’t turn me off (Bobby had a huge belly when I first met him and it surprised me then how I still found him appealing).  It’s just more about the fact he purposely skirted the issue of the dated photographs.

His smile was gregarious, but didn’t quite reach his eyes, which always makes me a little suspicious.

We shared a few drinks and his personality began to show – he was a jokester.  I am ok with that to some extent, but when it just. doesn’t. stop. it gets to be a little much for me after a few hours.  And he didn’t stop, all night.

I knew I was there for the sex and was more or less focused on that and disregarding the rest of it.  Jokes don’t really matter until they get irritating (or continue in bed, which they did) and I realized quickly he was the type of person to say something you want to hear instead of what he really means.  That doesn’t work for me.  I am not great at reading into someone and I am super-direct.  To me, that’s all a bit of game-playing.  Perhaps I do a little of it in text and banter, but not in person as a consistent behavior.

We had agreed on a specific spot for dinner that doesn’t take reservations, and I suggested several times we leave the bar and head that way, knowing the wait would be long.  He insisted it wouldn’t be that busy.  I finally gave up the debate because he is the type that knows better.  When we arrived at the restaurant, it was an hour plus wait.  He suggested we grab one more drink, but when we walked about a block away, he suggested we grab a bite to eat elsewhere “if that was ok with me.”  I voiced my opinion that I preferred to wait for the agreed upon restaurant and we kept walking and talking.    We went back and forth with suggestions until I finally said “Look, you clearly don’t want to wait, though you keep offering to wait, and it sounds like we should have just eaten at the hotel – so it that what you want to do?”  I was admittedly frustrated because he kept saying “whatever you want” when he totally didn’t mean it.

He agreed immediately and said he thought he was being polite.  I wanted ot say I thought he was being obtuse, but I figured it was better to keep my mouth shut at that point.

Things balanced out at the hotel when we sat to order.  He asked me if I preferred to eat on my own or could he order and we would share.  You know that I love that style, so I readily agreed.  Same with the drinks, we discussed trying some different and unusual cocktails together.  I landed on a Dark and Stormy which I know is one of ASV’s favorites and I can now count it as one of my new favorites as well.  Very reminiscent of a Moscow Mule.

Dinner was fun and the conversation flowed easily enough.  The only complaint was the jokes were continuous.  I’m not super good at distinguishing all the jokes he was throwing at me, and then that sets me off on the wrong foot or perhaps more defensive.  My x had exactly the same habit and I don’t like it.

The thing is, I am funny and silly, but much more about sarscatic or witty humor than joking.  If you are not looking at my face when I make a joke, you could easily minsontrue it’s meaning, but I make a lot of faces that clue my partner’s into my sarcasm.  I’m unsure how to better describe the difference in our sense of humor, but I would say his was more boy-humor, or more base, small zings.

We made it back to his bedroom and quickly fell to the bed.  We had been kissing on and off during our walk and he was a pretty decent kisser.  I sort of already knew the sexual chemistry was going to be ok as long as he wasn’t lying about his cock and oral skills as well! :/

The good news is that he didn’t lie about his enjoyment in bed.  He was eager to please and find what worked well between us.  We moved around and enjoyed each other for some time.  He wasn’t keen on using a condom and insisted he couldn’t cum with it on.  Oh well, too bad.   Eventually he jerked himself off and it was time for me to leave.

I didn’t hear from him the next day, nor did I text him.  It’s not worth the contact again, even if he is here every month.  The sex was so-so, but the jokes got on my last nerve eventually.  I was hoping he would stop them in bed, but he didn’t.  And they were not the belly laugh kind of jokes either, so I guess it’s just my own personal sense of humor.  I didn’t find him funny or enticing enough to go back for a second round.

Chalk that one up to decent vetting, some initial chemistry and so-so casual sex.  Not a total loss?!


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.

25 thoughts on “Casual, Flirty and Fun”

  1. One of the things I find most attractive about a man is a sense of humor. One of the things I find least attractive about a man is “joking” that is really a crutch 1) they use to belittle someone in order to feel superior (“I don’t know why that bugs you — I’m just joking!”) 2) used because they are uncomfortable carrying on a decent or thoughtful conversation (similar to people who giggle after everything they say — it’s a measure of how uncomfortable they are in a social situation) or 3) used as a pretext for attempting to show how much they “get me” and how “easy” our conversation is — because if we weren’t “clicking” then how could they joke with me the way they do? (Here is a hint — this is only true if I’m joking back. If you are the only one doing the joking, something is wrong).

    To have the joking continue into the bedroom??? Inconceivable! I’m all for having a great time and laughing in bed — but it needs to be a mutual thing — not an awkward thing.

    Liked by 1 person

    1. You’re totally spot on. It became awakes quickly and I think he does use it as a social style crutch. My X used to (still does) make all kinds of inappropriate jokes and they are just not funny…if this dude wore me down in one date, it’s no Wonder he doesn’t have a serious relationship.

      Liked by 1 person

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