I don’t really believe in regrets when it comes to dating. I’ve been on hundreds of first dates. People ask if it’s exhausting, if it feels hopeless, if it feels endless.
I always say no. Firmly believing every date is another step to finding what I want, even if that specific date turns out to not be what I want.
You’ve heard about the Big Three: Alex, Reid and Jackson.
I’m in the mood. Let’s dive into the others, the ones who I called boyfriends but prefer to not see them as such. I hid their existence, their significance from my friends, from myself, hoping at some point it would just dissipate.
I just happen to have this curse where I never really stop thinking about anything.
I still haven’t entirely figured out why I so prefer to discount these four men. Three of them were when I was in high school. The fourth was in college, after Jackson but before I was truly over him, if I’m being honest. The fourth is also a longer tale. I’ll break that down next week.
I don’t believe in the notion that young love isn’t love. Doing so forces young people into corners, shadowing how they feel and halting them from being able to make informed decisions about their feelings. Every tragedy starts with secrecy.
Here are all of the boys I loved in high school.
The first
The first man I ever had feelings for, the first man I ever kissed, the first man to break my heart.
The first man to teach me cruelty.
It started with a musical, Hot Micado. SJ took me to see it. I was still weeks away from coming out. I didn’t even really have a plan, or know how to formulate the words to say it yet anyway.
Then I saw Josh.
We stayed after the show ended to say hello and congratulate him on the performance. So enraptured, the wheels finally started turning in my brain that maybe I could finally say what had been holding me back for so long.
The turning point was a couple weeks later, when SJ told me Josh said he thought I was really cute. SJ laughed as they recounted this story, recalling they’d said I was “one of the straightest people they knew.”
I still remember the exact moment. SJ sitting on the couch in my grandmother’s apartment, me pacing across in the room.
This was my chance, I thought.
I still didn’t tell SJ, or anyone, at that moment that I was gay. It took a little longer.
A few days later I finally worked up the courage. I texted SJ.
“I have a crush on somebody.”
SJ, busy rehearsing for a musical and so used to me having a crush on one woman or another, replies, “Cool.” No, they did not ask who it was lol.
So I push farther. “Aren’t you going to ask who it is?”
SJ, “Fine. Who is it.”
Me, “Josh.”
What I didn’t know at the time was SJ happened to be sitting on a couch next to him as I dropped this bomb, shattering everything SJ ever really understood about my romantic life.
The reason for saying the words at that moment lay in my hope to see Josh in a couple weeks at SJ’s prom, to dance with him, to grow my budding crush into something that might turn into a date, a relationship, even love.
It all happened exactly as I imagined. The flirting. The dancing. The kiss. The feelings.
It grew even as disaster struck. I was in a minor car accident with SJ as we left the hotel.
I didn’t have Josh’s phone number yet, but he found mine. SJ’s phone died seconds after they texted him about the accident. He then went on a hunt with the drive of a journalist, texting people who knew me, having them text people who knew me, until one of the who had my number forwarded it along.
Minutes after the accident, he texted me to ask if I was okay.
We were fine, no injuries. Just a lot of irritating cosmetic damage to the Mustang.
We made it back to SJ’s, changed and met Jeremy at Cafe Brazil for a late night breakfast. Josh comforted me as I sat there, shaking and traumatized after what was my third car accident in just nine months.
Then it all fell apart.
I saw him again a few days later, but that would be the last time for weeks. Josh went from my first crush to my first frustration. He suddenly was never available to go on another date, to get dinner, coffee, anything. We texted and SnapChatted. It’s because of him I learned to hate SnapChat.
But that’s where it remained. Online forever. Eventually, I felt defeated and sent him a text saying I didn’t get what was going on and didn’t deserve to be strung along like this.
He replied that he just wasn’t really in a place to pursue anything.
Would’ve been nice to know before I wasted a month on him.
He’s done many terrible things to SJ since that made me despise him. Yet, I don’t have a single regret, regarding my time with Josh, at least .
It’s because of him I started to learn my own self worth. It’s because of him I learned the skepticism it takes to survive in this community.
It’s because of him I learned you can hate someone as much today as you did eight years ago and it won’t drag you down.
Don’t tell me holding onto a grudge holds you back. That’s nonsense.
The $2 billion boy
Like an idiot, I fell into the trap of dating another boy from SJ’s high school.
It was easy . There were so many gay, bisexual, queer, whatever people at that art school.
A bottomless well of men.
There I found myself, at yet another musical, Hair, this time at the school than outside it.
I was told in advance Holden had seen me at some Booker T. function and thought I was cute. Bored in my senior year and looking for the relationship that had eluded me four months before with Josh, I went with it.
After the show, I went up to him and got his phone number. We started texting immediately. All day every day.
He was the person who taught me how exhausting it can be to text 24/7. I didn’t learn my lesson, though, until years later with Jackson, who rarely texts.
He was also the first person to make me feel uncomfortable about my body image. Not that I wasn’t attractive enough, but that he was obsessed with it. I was as cute and hot of a boy as he had always hoped to find. His obsession fed into a fear that has haunted me since, that I’m only worthwhile if a man finds me attractive enough.
He just never stopped talking about it.
I eventually banned him from flirting before 10 p.m. It was exhausting and prevented us from having anything that resembled a meaningful conversation.
Even that didn’t work. He abused the rule and would start flirting the second the hour struck.
We went on three dates over three weeks. We became boyfriends after just one date.
That first date he had chocolate delivered to the Pac Sun where I worked. After I was off, he picked me up and we went to True Food, which he chose to accommodate my food allergies.
He paid for everything, including our ice cream afterward.
There was only one hiccup. As we walked into the first ice cream shop, he suddenly grabbed my hand and dragged me back out the door.
His father, who he didn’t really get along with, was inside with his stepmother and younger brother.
We raced back to his car, out of breath and stressed.
A beat passed and we went to a different ice cream shop.
He then took me on a drive past his mom’s house in Highland Park. A mansion of which I could barely fathom, it was then I found out he was the heir to a $2 billion fortune. His family, I learned, was one of the few to make it out of the 1929 Great Depression in Dallas without losing it all.
As I started to push Holden away, I leaned on my mother for advice. She jokingly told me, “It’s just as easy to fall in love with a rich man as a poor one.”
I could’ve stuck with it. I could be among the ultra wealthy. But would it have been worth it? Probably not.
We were going to different colleges anyway, and I don’t do long distance.
By the time we reached the third date, I was over it all. I broke up with him as we walked out of Coffee House Cafe. I’d already been pushing him away, and he’d sensed it. Though I recall him telling SJ he thought it was rude to still go on the date at all.
I don’t know what the best route would have been. Break up when we got there and we all go home? Do it while we’re eating? Send a text and cancel the date altogether?
My first act of cruelty
I’ve never pretended to think I am blameless in any of these situations. But it wasn’t until Riley that I broke a rule I’d set for myself, a rule I’d created, in fact, because of what Josh did to me.
As my connection to Josh fell apart, he began the slow ghost. Replying slower and slower, or only when he was horny.
I told Riley about what happened when we started dating. I told him about how it had affected me, how I vowed to never do such a thing.
So virtuous.
Such bullshit.
I dove headfirst into this relationship. It was the longest of the three. About six weeks or so.
I also saw him the most because unlike the other two, we actually went to the same high school.
But like the other two, he was also a theater gay.
We got ice cream — the high school version of getting drinks, I guess — after one of his rehearsals. I kissed him in the parking lot, so nervous, but so full of desire.
When this relationship came to fruition, boyfriends, it was the most real of them all. We texted, but not as frequently as the other two. We had dinner more than just three times. It wasn’t as rushed.
But after a month, I found myself distracted. The relationship, and Riley, became like a nat swirling around my head.
I couldn’t bring myself to truly focus on him because I was more interested in my primary relationship — the yearbook I was creating.
After three long years, I was finally the yearbook editor-in-chief. All decisions went through me, but I also felt an extraordinary amount of pressure to make it perfect. Unlike my predecessors, I was only editor-in-chief for a single year before graduation.
The book had to be flawless. It had to be groundbreaking in a way the other books weren’t. It had to lay a path to higher heights, to more awards, to a level of power that would put my school in the same tier as the wealthy ones that always dominated.
A relationship, to my workaholic self, was an inconvenience, something that would just take time away from what I really cared about.
I drifted away from Riley. The holidays arrived and we lost the connection of school. I replied less and less often. Not wanting to deal with the situation. Not wanting to confront him, or myself, that I just wasn’t in it anymore. That I didn’t care for him anymore.
The problem was that I just didn’t care at all.
I didn’t care how my actions affected him.
I wasn’t concerned that I was doing the exact thing Josh had done to me.
My first act of cruelty was that of thoughtlessness.
When I finally broke up with him, over text, it was to make the problem just go away. That’s how I’d become to view the relationship, as merely a situational inconvenience.
The hope was to just end it and move on. I wouldn’t have to think about him anymore.
Thankfully, I wasn’t let off easy.
He called me out for the slow ghost, for pulling away and not explaining why, for dragging out a relationship that should’ve ended much sooner.
I can’t remember how I responded. I wouldn’t be surprised if I didn’t say anything at all. I deserved some kind of repercussions, at a minimum.
All of the boys I loved before
Collectively, the time I spent on these men — three months — was triple the length of my relationship with Alex. It was also less than half the length of my relationships with Reid and Jackson.
Josh, Holden and Riley are a vision of the past, a remembrance of love, frustration and impetuousness.
Thinking of them reminds me of my long-held belief that every relationship, every date, every kiss contributes in a useful, if not always positive, way to how I approach dating now.
My actions, and that of these men, are reflected in later relationships I had. Like a mirror image, I went through these experiences and claimed to learn something but realized nothing had changed.
I forgot to shatter my reflection to build a new one.
I’d like to think I’ve made progress since then. I think I have. I know I better understand cruelty, at least.
As Taylor reminded me last night,
“Teenage love taught you there’s good in goodbye.”
More than just my Love Story
30 Gay Love Songs: Men Singing About Men. (Billboard)
Why are there so few openly gay male athletes in sports? We asked ChatGPT. (OutSports)
“No Love Is Ever Wasted.” (New York Times)
Note: The names of the people in my columns have been changed to respect their privacy — and to allow me to spill a bunch of tea about them without remorse.