Pondering My Last Date

Anthony was my last date before my 2 week hiatus from the dating apps.  He was the first man to meet who worked in my industry, so we had plenty to speak about.  It took about 3 weeks of back and forth to finally meet.  He was consistent in following up, but never spoke for too long as we attempted to make plans.  I was clear I wanted to meet him, but our times were just not lining up.

We finally landed on a date last Friday night.

I was pleasantly surprised when he walked in.  I thought he was good-looking in the photo, but more cute than handsome.  My opinion changed upon meeting him.  He was 6′ tall and solid.  He was very charming and engaging.

We had a lovely dinner that lasted at least 3 hours, then he asked me to the bar for one more drink.  We spent another hour together.  During dinner we chatted about so many subjects and laughed easily.  He was kind, well-mannered, gregarious and easy to talk to.  We shared plates and he was sure to put food on my plate and watch my wine glass.  He knew exactly how much I ate and drank.  You know I love these small things.

He walked me to my car and I admit I leaned in for a kiss…that he didn’t seem too interested in returning!  Oh!  A bit of a surprise there, honestly.

We had spent close to 5 hours together by the time we separated and headed home.  He text to check if I was home.  I replied that I was and thanked him for a lovely evening and he replied he had a nice evening as well.

I would guess I am not going to hear from him again, though I can’t put my finger on just what it was that had him go from interested to not interested. It could have been when he said (again)  “you can call me Tony” and I reeked with “But, I love Anthony!” and he noted “oh, that’s the x?” and I nodded in agreement.    It could have been as he was questioning me about what’s next in life and I said I didn’t know, multiple times, until I finally joked it away saying “perhaps I will just marry a rich man!”  It could have been anything.  I admit I am unsure, but I felt it at the very end and perhaps I missed earlier cues once we were at the bar.

Maybe it’s a vibe I’m giving off during this weird phase I’m in.  When anyone meets me, I am at my best-most-confident-self.  It’s a bit hard to reconcile that with a woman who has been unemployed for almost 6 months.  Clever men pick up on it quickly and also seem to want more direct answers as to “what am I doing next.”  I really went over the date in my mind, but couldn’t pick a point that turned the date in the wrong direction.

Maybe I spoke too much about my kids or my x (kids maybe, didn’t really discuss x though). Not enough chutzpah about finding a job sooner? Men are definitely put off by me not working when they get the vibe that I’m well spoken and educated. The two don’t fit together: being unemployed and bored doesn’t mean with my personality and it’s confounding them. Maybe they don’t want the younger entitled kids to deal with or think my hands are too full. I really can’t pinpoint the last few I’ve lost from the calls and first date.

Oh well, one more week of no dating apps is just fine for me.  The fun can begin next week again!

By the time this posts the apps will be back on after a full 10 day break. So let’s see what happens in the next batch!

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.

6 thoughts on “Pondering My Last Date”

  1. Aw, that’s a bummer. It’s been my experience that so many times, we can have promising first dates, and then… crickets. I do tend to think that in most people’s hustle-and-bustle lives, while they like the idea of dating, the reality is that they are already operating at full capacity and, in practice, don’t have the bandwidth to commit to a new relationship, even a casual one. I’m guilty of that, too! There’s a disconnect between the fun of the moment of that first date, and the reality of adding another person to their lives. At least with most people I’ve online-dated in the last handful of years, there seems to be this understanding that it’s socially acceptable to broadcast one’s change of heart by retreating like this, given that there isn’t enough of a relationship yet to demand greater accountability. We’re maybe too vulnerable to have someone we don’t know that well explain why they are rejecting us. If, however, you are genuinely puzzled as to what you might have done and want some feedback, maybe there is a way you can reach out to Anthony and say something more or less along the lines of, “I had great fun with you. If my intuition is right, you enjoyed our evening, but aren’t looking for anything more. If so, I’m a bit sad, but also totally cool with that. I am just getting back on my feet with dating after a break and am genuinely interested in some feedback and feel ready to receive that non-defensively. Was there anything I said or signaled that gave you reservation? I might not have even been conscious of it. Don’t worry, I wont argue with you about this and use it to barter for another date.” And then you have to be ready to hear his feedback and NOT at all be defensive and release the beautiful fish that he is back in the ocean so you can cast your line again with a stronger and clearer sense of self. If I were him, contemplating a new dating relationship, I would get some reservations about jokes around looking for a rich husband, and more so about you not having clarity yet about where your career is going. I wouldn’t need someone to necessarily have a job, but I’d need to know that there were in a relatively high functioning place with looking for one. xoxoxoxo

    Liked by 1 person

    1. Thanks for such great feedback!

      I do feel that men are put off by my lack of employment. They can’t quite reconcile the personality in front of them compared to someone who just isn’t working at all. I wouldn’t want to date someone unemployed so I get it. And, since the joke stands out to me, I tend to think it was a misstep as well.

      I don’t care “enough” to ask his feedback. But my reasons for that are more because he is in my industry and I want his help. I reached out to him to ask some business questions and he shared his email and asked for my resume. So he’s a good guy and I want zero pressure about the dating if he is going to be a good business connection.

      Liked by 1 person

      1. Totally NOT complaining!!

        I googled him and now realize he absolutely uses Tony for everything so maybe it really was the “I prefer Anthony”
        Comment! Lol. I wrote and addressed him as Tony for work purposes! Need to keep him happy!


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