I’ve been able to do some new things since I started working with a therapist and learning about attachment theory, understanding how I feel about myself, unraveling my relationship with my mother, etc.

I’ll tell you, dear reader, what I’ve done (and it's been a real twirly let me tell you).

I was dating a gal, who I was genuinely interested in, and I was able to be vulnerable about my feelings towards her and about another matter, early on, that was a problem. The early problems revolved around being sexual with one another, I was having considerable anxiety which prevented me from engaging in the physical act (and I guess prevented the emotional connection as well). Each conversation was healthy, given its context. The sex talk was challenging because, in the past, I would have just walked away and not bothered. But this time I brought it up and I felt such relief after. Now, it’s likely she was turned off and tuned out of our budding relationship as a result. But, you know what? If she doesn’t tell me, it’s not my problem—I can ask and I can provide safety to speak up but I can't make people do what they don't want to do. Vulnerability is the ultimate game of cooperative hot-potato (I know, that’s a weird fucking analogy, it’s the best I got). When I told her how I felt (this was after the sex talk), that conversation was positive but it was clear that she wasn’t down for exclusivity with me. Her actions showed her interest. She broke her foot and had been out of touch, the only interactions we had were when I texted or called. I last saw her a week before Christmas. I bet that she wouldn’t reach out to me if I didn’t contact her. Sadly, I was right. Oh well.

Again, you can’t make people act the way you want them to. You gotta let people do what they’re going to do and sometimes you have to let them go or let them hurt you—I know what I said but trusting people means that sometimes you get hurt in the process.

Back in September, I went out to dinner with this friend I know, we used to work together. We stayed in touch. I always had a feeling that she had a passing crush on me but I never addressed it, nor did I agitate it, or at least I didn’t think I did.

At dinner, my friend and I were catching up. We had a bottle of wine, probably a mistake. I noticed my friend starting to get a little nervous/squeamish. She excuses herself and comes back some minutes later, grabs the stem of her wine glass with intention, and swallows nearly the whole glass. It was a sight to see. She took a deep breath and confided that she had strong feelings for me, that she liked me.

In the past, I have gotten into many of my relationships that way, being passive, letting the other person perform the labor of being vulnerable, and going with it, even if it was someone with whom I didn’t have a strong connection.

I told my friend that I was flattered, honored, really, and I was upfront with her. I told her that I didn’t see her that way and that I was sorry. She cried, and she scurried out. I followed her outside after settling the bill. She didn’t want to talk but leaned on me while she cried. I didn’t have words of comfort—I didn’t know what to say and I already felt like a piece of shit and not just for deflecting my friend’s profession of her feelings for me. Ultimately, I did the right thing. Authentically, I didn't share my friend's feelings of romance and I made that clear.

I don’t mean any of this to read like a humble brag but I guess it does. To hell with it. I knew I had a choice to make and that I had to make better choices and conduct myself in a way that aligns with who I want to be. I want to be truthful, loving, able to be loved and share my life.

An old friend, who had an unhealthy attachment towards me, used to say about me: You’re in love with being in love. That I didn’t really want all that comes with love, I only wanted the in love part of it. There is some truth to that, I think. The guts of a relationship are difficult to hold, especially if you're prone to insecure attachment patterns like I am. Captain Carelli’s Mandolin has some great lines about love, about it being a temporary madness, that being in love is something any fool can do. But love is what is left over when all the other remnants of being in love have burned away. I’m generously paraphrasing but I think you’ll get the gist here. Right?

Managing relationships, managing someone else's concerns and feelings isn't something I've spent a lot of time thinking about. It's not that I don't care, it's that I'm concerned with a lot of other things, things that aren't necessarily real. I worry about things that aren't necessarily a real problem, they're figments of my past unresolved trauma. Specifically, my self-image is problematic, I have a low opinion of myself. I fear financial destitution, from growing up poor. I also fear conflict, letting people down, or upsetting people because I fear what that says about who I am as a person. You see, these things, these fears, can be addressed in communication (and a lot of therapy) and that's something that happens when you get deep into a relationship with someone, after the initial excitement of being in lust or in love with someone has waned a bit.

Since I’ve been doing the online dating thing again, I’ve worked to be more intentional with it. I’ve also worked to be more upfront with how I feel, particularly with women who I go on a date with and don’t feel a connection or just feel like there’s no chemistry ahead of doing a date. Yeah, it’s weird but hear me out.

I’ve gone on a number of dates since October (when I jumped back into the dating pool). It was more a quantity over quality situation. I went on one date that I felt like I should have bailed on but I went anyway. I can’t tell the future. Needless to say, the date was a miss. It wasn’t bad but there wasn’t a desire for a part two and I’m sure my date felt the same way. We messaged later and I said as much (with better wording of course) and that was that.

From that point on, I’ve been able to experience less anxiety about letting people down or hurting them, which were reasons why I never bothered to tell women in the past, I would just ghost them instead. I had a couple of women tell me and I have told a few women. Nobody died. One person called me an asshole for telling her I didn’t think we were a fit. Everyone is dealing with stuff, I didn’t take it personally.

After my last series of dates, I think I’ll take it easy for the time being and get back out there after a breather.

Something else I’ve been doing is what I’m not doing. I’m not reaching out to past flings. Don’t get me wrong, I want to but I don’t. It doesn’t serve me (or them). I want something that’s real with someone else. While I don’t have things figured out completely, I know that retreading past relationships won’t yield what I want. Revisiting past flings is a habit, a coping mechanism for dealing with loneliness—it’s an attachment pattern to engage in these activation strategies.

I’m trying. I’m leaning the right way, I feel off, and I think I know why.

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Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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