Greatest Hits: My Head's Favorite Dating Insecurity Tapes
I don’t date much. Never have. I am a gay man in my thirties and I have never been in a relationship. Most days I am fine with it. I am naturally an introvert, so being alone has never really been much of an issue for me. But there are times when the lonely voices in my head start to play their favorite tapes; the greatest hits of my insecurities about dating. In spite of all the work I have done to love and accept myself as I am, these tapes still play in my most vulnerable moments.
As we hit the seventh month mark of the COVID-19 pandemic in the US I had one of those moments. I was swiping away on one of the myriad apps that people use to attempt to find love when I matched with a guy. We started chatting. The conversation flowed very easily, much more so than it had with anyone else in the past couple of years. We spent a few days chatting on the app and then decided to meet at one of the countless walking trails that are scattered around Los Angeles for a socially distanced walk date. It was short because we’d set it up for late in the afternoon, forgetting that November brought with it shortened days. It was nice though, even with the shortened time frame. I felt oddly comfortable as we talked on the route we chose, the darkness descending around us. It was a little awkward, as first meetings sometimes are, but I thought the conversation flowed just as nicely as it had over text. He must have thought so too, because at the end of our twilight walk he asked if he could buy me dinner sometime.
The oldest of the tapes my dating insecurities play is “everybody leaves me.” Even though this is the one that has been broken down and examined the most, both on my own and in therapy, I’m not sure where it originates. The times that come to mind are childhood friends who stopped speaking to me for reasons that were not clear to me. I hate an unanswered question, and every example I can think of someone leaving me, in whatever sense, was always without me knowing why. It got to the point that I stopped calling people my “best friend” because it seemed like whenever that happened, the friendship would dissolve not long after. This continued into adulthood, and was so ingrained that the first time I used that label with the person it now applies to I immediately thought “oh, well, there she goes.” She’s still around after a decade, but that isn’t enough to disprove the theory to the most insecure part of me, which says she is just the exception that proves the rule.
Enter the closest I have come to being in a relationship. It was my second year of college. We’d been friends most of my freshman year before things began to take a turn. It was exciting because it was the first time that I was falling for someone I actually had a chance with (i.e.: someone who wasn’t straight) and someone who showed some interest back. Even so, as much as I wanted it to be, I knew from the beginning it wasn’t a good fit. With a lot of reflection, examination, and analyzation, I’ve determined that a part of me knew that we weren’t compatible, that I would be hurt, and fell for him anyway, hoping that getting hurt bad enough would make me straight. The realization of just how deep the root of my own internalized homophobia goes is was as terrifying as it was enlightening. It has allowed me to begin breaking down some of my fears and issues with and about my sexuality, but means I am constantly finding little ways that it influences things. Probably one more reason that I don’t attempt to date more; because then there will be more opportunities to expose that damaged root in my psyche.
With all of the unknown born out of this, I find myself desperate for definition in so many situations. This led me to ask this guy one night, a few months into the situation, what we were. His response was “we’re just us.” The most rational part of me saw the red flag, but the part desperate for his approval ignored it, saying that it was just modern, we didn’t need labels.
I found out he was leaving town from the invite to his going away party on Facebook. Four months after we were “just us” he had decided to leave, without even a hint that I could see. I wouldn’t be able to attend the party. When I texted him about it he said something to the effect of “oh, that’s too bad.” And then he moved a few hundred miles away without any word about why, or “us”.
“Everybody leaves me.”
A couple of weeks after our walk date the App Guy and I met for dinner at a bar in West Hollywood. We sat near a heat lamp on the patio after shopping for some face shields to prepare for the coming Black Friday at our respective retail jobs (November 2020 after all). The conversation was once again flowing nicely. There was laughter and the nerves I felt were eased by a good feeling in the pit of my stomach that I had so rarely felt in such situations. At some point the topic of past relationships came up. I said I’d never been in one and gave a very truncated explanation of the “we’re just us” situationship, but didn’t dwell on it because I’d spent more than enough time doing so in therapy, and didn’t want the specter of that guy coming on this date. The conversation continued in the easy way it had before. At least as far as I thought.
Once the plates had been taken away he looked at me and said “This has been great,” weighted with a “but” so heavy I could practically hear it hit the floor. He thought we should back up and communicate as friends for a bit, citing my lack of relationship experience as his main concern.
Tape two might be the loudest when I approach a dating scenario. It is a lovely mash up, pairing the classic “what is wrong with you” with a slightly more specific “you’re so bad at this.”
In the decade between “just us” and the App Guy I went on two official dates. Part of that was due to the fact that I lived in a small town in rural Colorado, so the pool of dateable gay men was not very big. Between that, getting my degree, and working after college I didn’t allow myself much time to try.
There were a couple of times that I built up the courage to ask guys out. One came a couple years after “just us.” He was a fellow college student and when I finally decided I would ask him, Winter Break came along and I didn’t see him. Rather than allow my overthinking mind to talk myself out of it completely, I sent him a Facebook message. It was 2010 and it was a more common form of communication than it is today. I never got a response and he didn’t mention it when we saw each other again. “You’re so bad at this.”
Maybe another year later I asked out a different student at the college and he actually agreed. But before we could follow through that cursed Winter Break came along. When classes resumed a month later and I asked when he wanted to go out he said he’d changed his mind. Apparently he was interested in someone else. “What is wrong with you.”
The next couple years were focused on graduation and trying to support myself with my private music lesson business. Still in that same small dating pool with only slightly more time than at the peak of my degree I didn’t bother trying to find anyone. Then came my move to Los Angeles. Designed to intentionally implode the crazy schedule I found myself in, I now had time, so I figured I would give it a shot. I would be in a bigger pool, so my odds would be better. A couple of ghostings after asking to meet only made the tapes louder. Finally after a year or so someone asked me to dinner. I agreed. We met. It went well. He never returned another communication. “You’re so bad at this.” Thinking as objectively as I could I thought that there wasn’t any obvious reason why I should be rejected; I wasn’t bad looking, I was smart, funny. These things said there had to be something else wrong that I couldn’t quite figure out – something that men could see that made them run away, but that I couldn’t. “What is wrong with you?”
I was stunned by App Guy’s proclamation that we should take a step back because I’d never been in a relationship before. I managed to gather myself enough to ask him what his fears were. He said there were a couple of reasons that were more to do with him than me, but the big one was that he had been in relationships with guys in similar situations before and found them too possessive. I assured him that he wouldn’t find that with me. Given my fierce desire for independence, if anything the opposite would be true. I asked him for a chance to prove that I wasn’t what he feared. He said he still wanted to talk, but to not expect more than friends. I offered to give him a ride home in spite of my desire to run and hide from the mixture of vulnerable feelings swirling in my body. We continued talking about other things, but not nearly as easily as before. We got in my car and as I pulled away from the curb he said, “maybe you’re right. Maybe I should give you a chance.” From there the conversation resumed the ease it had earlier in the evening. At one point he even mentioned how excited he was to tell a coworker how well the evening had gone. We made tentative plans to get together again later the next week.
The plans never came to fruition. The spike in LA’s COVID cases took an ax to that. He insisted that he wanted to keep talking and that he would see me on the other side of the new lockdown.
The text messages quickly devolved to him giving me monosyllabic answers to questions like “how was your day.” I spread out such inquiries, paranoid over the thought of seeming “too possessive.” The last time that he texted me may very well have been a mistake; a few texts into the conversation he said, “whoops, wrong person,” which I assumed at the time referred to just one in the string of messages. Looking back though I think he hadn’t meant to text me at all. So I decided that I would not text again. I would respond if he did, but I would not be the first to do so.
Not only did he never message, he unmatched me on the initial app, and unfollowed all social media. It is probably better, because even if we had resumed anything I’m not sure I would have been able to move beyond the “too possessive” and “you’ve never been in a relationship” paranoia. And even though I’ve never been in one before, I’m confident saying that walking on eggshells isn’t the way a relationship should start.
It hurt. It had gone so well in the beginning and to just be dropped like that (“everybody leaves”) hurt. One major frustration was that I know that I have done more work on myself as a person than so many people who have had relationships. It circles right back to “you’re so bad at this. What is wrong with you.”
There is a third tape that gets louder as I get older; “maybe it’s too late for you.” Maybe it’s too late for me to find a first relationship. I can’t decide if the thought is depressing or freeing. It could be incredibly feeing. I mean, think of all the time I could save if I just gave up any notion of a relationship ever happening for me. It could be glorious, the things that I could do. Then there are the lonely days; the days when it would be nice to have someone ask me how I’m feeling when I walk in the door. Days when it would be nice to have another person to help with simple things like laundry when I find myself overwhelmed. Days when it would just be nice to sit on the couch with someone, leaning against each other in a rotating set of positions as we go about shared or individual nothings.
Contrary to what so much of our popular culture tells us, I know that I do not need anybody to complete me; that I am perfectly fine on my own. I also know that there is a difference between needing something and wanting it, as well as a difference between wanting something and being willing to put in the effort it would take to get it. The thing about tape number three, is that I’m not worried it’s too late because of my “lack of experience” in relationships. I’m more concerned it’s too late in the sense that I will ever be willing to try. Because with each failed attempt, I find myself more and more exhausted with the idea of beginning the slog again.