Situations | the Urban Dater

It’s been a couple of weeks since we had our Good Goodbye. I can’t say I miss her… yet. I’ve taken time to think about everything that’s happened this year.

It’s been a calm year for the most part. My dating life has been active and positive. I’ve gone on a lot of dates, and I’ve dated more than I ever have previously. While the quantity of dating I’ve done has been nice, the quality of it has also been nice, even if it hasn’t led me to a committed relationship yet.

What I’ve talked with my therapist about and what I’ve been juggling mentally is the nature of the situations, relationships, and situationships (I guess) that I’ve been involved in. Why didn’t they last? Was it me? Was it them? Both? Is this even the right question?

There was Nora. We went on four dates. Not a kiss to be had among them. After our first date, I could tell this wouldn’t be a thing. While she looked like Anne Hathaway and kinda sounded like her, too, it didn’t feel like there was a draw between us. After a series of one-off dates, I wondered if I wasn’t giving things enough time. I decided to give it more time with Nora, but it didn’t matter. It didn’t work anyway. I’m now staring at two clay pots I was gifted, perhaps for my effort. There was no connection there. Nice person and pretty and funny but with no spark.

Then there was Nikki. Nikki and I dated for a hot minute last year. We had gotten intimate the first time, and she started crying. She wasn’t ready to be intimate with a new partner, fresh off a breakup with a previous partner (or my penis was that horrifying). I held her, and we talked, and then I went home. I called her the day after, we talked some more and agreed that dating wasn’t a great idea.

After a little more than a year, Nikki reached out on LinkedIn. We met up for wine that Friday. While I had an inkling of an idea that she might be reactivating our connection, I assumed platonic vibes. And after we made our way to a dive bar, I walked Nikki back to her car when she shoved me against a brick wall and kissed me (she was tall, and I liked it). And so we went on to date for almost two months. While we had good, healthy conversations, it was difficult to connect with one another. I didn’t feel connected to her romantically; I just wasn’t into it. She’s gorgeous, smart, sweet, and nurturing… But I couldn’t get into it with her. I had platonic feelings towards her.

We had a talk about things; I let her know what I was feeling. We dated another week and talked some more; I told her I didn’t think we should date and that it wasn’t the right fit.

Then there’s Monica. Tiny but mighty. She gave off asshole vibes on our first date. She was verbally punchy with me, demanded to see my credit score on our second date, and said stuff meant to shock me. It was a little showy, but I roll with chaotic behavior well enough, if you know me.

Monica and I had some hot fuckery and dated for over a month. I took a trip to Oregon and pondered whether this was going anywhere or not. She lived on the west side and did not want to go to my part of town. She took my revelations of having a kid, traumatic upbringing, murderous father, etc., with aplomb. But when I revealed that I didn’t have a college degree, her reaction would have you believe I slapped the Pope on the lips! Her reaction was surprising.

She viewed her friends who attend therapy as something of a novelty. The anxious one, the spontaneously sad one… All of my friends are drama queens; she would often proclaim. Now, I’ve got my own mental baggage (that I go to therapy for), and I’m not saying her view of her friends is necessarily wrong, but it rubbed me the wrong way. I suggested that she might not want to refer her friends as exaggerated symptoms. It was met with a chuckle and summarily dismissed. Our views on mental health differed quite a bit.

It was clear to me that Monica and I didn’t connect on an emotional level. Eventually, I told her I needed to end things. Monica agreed saying I feel the same; I just figured you’d say it first since you’re the mature one and all. I don’t think I’m all that mature, honestly, but that was that.

And then, most recently, was the younger gal I’d been seeing. We saw each other as a temporary arrangement, had fun, knocked boots, took liberties with one another’s bodies, and went our separate ways. And that was that.

And here I am. Still single. Taking a break from it all to collect my thoughts, keep doing my work, and try to make sense of the year that’s been thus far.

Was I exiting these situations because I was afraid? Did my unhealthy attachment style get triggered? Or was I just not interested?

I tend to believe that I wasn’t interested and not triggered. I remained present, communicated, and often initiated the dialogue in each situation. We don’t hand out gold stars for this, but it’s good to work on your weaknesses. Yes, I’m giving myself a pat on the back. I’ve never been good about initiating uncomfortable dialogue in romantic situations.

That said, none of the situationships mentioned above lasted more than a couple of months, and time and consistency are key metrics for measuring a person’s behavior. Have I actually changed? Have I made progress? Am I still at the mercy of the bullshit I’ve been working on these past couple of years? In some ways, I feel better about myself and the areas where I’ve struggled. In other ways, I feel like there is so much further to go.

I can say that every conversation I’ve shown up for hasn’t been as bad as I feared they might be. I feel more confident sharing how I feel and expressing what I want, and that’s been freeing. I’ve been able to do this in a romantic context and also in a work context, too. It’s not helpful to say that I wish I had learned how to do these things decades ago, but I wish it anyway.