It is generally bad when people look back on some dumb, bad, or confusing thing that happened to them in teendom and start to believe that it explains whatever shitty state of being they find themselves in now. However, I am unhappy and willing to give it a try. Eat your heart out, Sylvia Plath. The particular manner in which I lost my virginity, and its subsequent fallout, may be worth examining. It involves three girls (this will make sense as you read on), and starts in a mental ward.

When I was sixteen, my parents had me committed. They couldn’t really deal with me anymore, which was fair, and figured putting me in a ward would be a surefire way to keep me out of prison, which was also fair. Minors don’t have rights in any meaningful sense, and I’d done sufficiently goofy and dangerous things to serve as reason enough for putting me in a padded room. One day it was just sort of decided, and we drove as a family to a big white building and in I went. This didn’t strike me as a terrible deal, really. I hated living at home, but had no money to go anywhere else, so this seemed like a unique and potentially interesting way out.

Mental wards for teenagers are about as interesting as you’re probably imagining, though the atmosphere is much less oppressive than you’d think. The focus is mostly on making sure nobody commits suicide, since attempts at that are how about 85 percent of the patients end up there, so it’s quite a bit of just hanging out with other freaks, druggies, and maniacs. And while I had been a total loser in school, with this crowd I really wasn’t. Everyone was a loser there, so just not having attempted suicide made me close to the alpha male.

It was a nice feeling, suddenly not being a loser, and I enjoyed my time there. Incredibly, this ward was co-ed, and it was there that I learned what it felt like to talk to girls and have it go well. That was a damn nice feeling as well. First, I met Mickie, with peroxide blonde hair and piercing blue eyes. Then she was released and I met her aesthetic opposite in Shy. I thought the world of both of them, and both teased me enough about being a virgin that I figured they must have something in mind for me.

I was right. The day I was released, Mickie and a few others who had been in with us came and picked me up from the hospital to go celebrate the freedom of the last member of our little clique. We all got stoned and drunk and had one helluva time. Mickie pulled me into a back room and we started making out. I remember feeling indestructible, truly on top of the world. The mental ward was behind me, it was July so school wouldn’t start again for months, girls wanted to fuck me, and I was as happy as I’d ever been.

There was just one problem: while I liked Mickie a whole bunch, I liked Shy more. I was, to coin a phrase, in love with Shy. And I’d always heard that you were supposed to lose your virginity to someone you love, that it was more special that way. So incredibly, I told Mickie “no,” and we just hooked up. Looking back, I cannot believe that I did this. You probably cannot believe it either. Fuck.

The rest of the summer was weird, to say the least. Mickie and I lived relatively close to one another, so we became “friends with benefits,” really intimate ones. Meanwhile, Shy lived far away, and neither of us had cars. We talked on the phone all the time the way teenagers do, and our conversations were wonderful. Mickie’s life had largely gotten back on track since she’d left the ward, but the same was not true of Shy and I. We were both still in pretty tense situations at home and with incredibly uncertain futures. The talks we had about it all, about what might be waiting for us, about our parents, about what we feared might come next were incredible. Sometimes it felt like there was no one else on the planet we could talk to. But when it came to actually seeing one another, it was only once a month or so.

It might seem like I was leading both of them on, but I wasn’t. In my fucked up and inexperienced head, I really thought what I was doing made sense. Shy and I weren’t dating, so I could do whatever I wanted with other girls. But since I wanted to lose my virginity to Shy eventually, I wasn’t fucking Mickie; just “everything but.” Yeah, I know now that none of this makes sense.

After plenty of “will they/won’t they,” Shy finally told me that she did not want to be my first. She was worried that if she was, I’d always be attached to her for that reason and that reason alone. Instead, she wanted me to lose my virginity to someone else “for her” (those were Shy’s words) and then come back to her. The catch was that the girl had to be someone I didn’t care about, someone fairly random and not well-known. For some reason, all of this made perfect sense to me, and I agreed.

Mickie obviously meant too much to me. I wasn’t head-over-heels for her, sure, but I liked her quite a bit. So I needed to find someone else. I brought this up to a buddy of mine who was at a local college, and he told me he knew the perfect girl: the campus slut. Her name was Kayla, and after my buddy introduced us one night, she proved to be as slutty as her reputation promised. At the age of twenty, she fucked a sixteen-year old she’d met just hours ago.

If you were going to guess that after this happened Shy and I got into a huge argument and stopped talking and never had sex, you’d be right. Genius that I was, I told Mickie the whole tale, and ended with what I saw as the bright side to the whole ordeal: she and I could actually fuck now. Of course, Mickie had been secretly in love with me for months. When I told her everything, she could not stop crying and told me I’d hurt her more than she’d thought possible. We never spoke again, except the time I called her like a year later and she told me to go fuck myself.

Unsure what to do, I figured it would be best to just start fucking Kayla all the time. Months later, Kayla confessed her undying love for me. I didn’t feel the same in the slightest, and we fell out of touch. Someone told me she’s a doctor in Boston now?

All of this sucked a lot. I’m an idiot. I basically got played, and in getting played, managed to hurt two other girls quite a bit. I wish I’d realized that Shy was fucking nuts earlier and then found it in myself to love Mickie as much as she loved me. Kayla should never have entered my life. It’s weird how when you’re a teenager, you feel so grown up. You feel like you’re basically an adult and that everyone holding you back should get out of the way. But it isn’t like that. You’re an idiot, and no one can convince you otherwise. Fuck.

Anyway, these days I still have lots of destructive relationships with women that end with everyone getting hurt and regretting the whole thing. It has happened enough times now that I have begun to wonder why. I no longer think this racetrack of broken hearts is a coincidence or something I’ll grow out of. The second half of my twenties is here and it isn’t getting any better. I want answers. I want some God to come down from the heavens and explain to me why things keep going this way. But that’s not going to happen. No shrink is going to figure it all out either, and then give me a magic pill to make it all better.

Well, as far as answers go, most people these days claim it’s all in the past. You’re an asshole because Daddy hit you. She has trust issues because of her distant mother. He will never have a stable relationship because his childhood home was so broken. If that’s the case, I’m pretty sure the above story of how I lost my virginity explains a lot. Fuck.

One last thing: if you had to say who I lost my virginity to, which of the three girls would you name? These days I’m thinking it’s Mickie. “Everything but,” when it really does include damn near everything, gets you past that “virgin” state of mind. Then again, maybe I’m just rationalizing, and it’s just that’d I’d have really liked for it to have been Mickie. Fuck.

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“Virginity Lost” is an excerpt from Richard Power’s new memoir, Letters from a Heartbroken Pervert. You can purchase the book from Terror House Press here.