Before I lost my virginity, my views on masculinity had been woefully misguided by pop culture and the wild hormones of male adolescence, as they are for most young men. I assumed getting laid was the only path to manhood and that machismo was paramount to any other quality men should possess. I remember thinking that if I just had sex, all my insecurities would vanish. My pubescent state of mind was too sheepish to know any better.

I grew up your typical suburban teenager whose off-book sexual education was shaped by block quotes in men’s magazines and teen sex comedies. At the time, those movies presented sex as the gateway to masculinity. The main takeaway from the first American Pie film, which sparked a renaissance of teen-sex comedies in the late 1990s and early 2000s, is that you had to lose your virginity before college less you spend the next four years a miserable schmuck. Two years later, American Pie’s sequel moved on from virginity to kinkier territory with a threesome subplot that literally presented the sex act as a one-way ticket to sex-god status. I was immediately drawn to the allure of it: two women at once?! Slowly, for me and probably every other teenage boy out there, the threesome morphed into a symbol of achievement. Because at the time, having a male-female-female threesome represented everything I wasn’t: wild, confident, outgoing and full of kinetic sexuality. I put the sex act on a pedestal and for almost a decade, it sat there, mystifying in my head.

The chance of fulfilling my threesome fantasy still seemed far-fetched, but this was New York, and I was single again.

I was a late bloomer, so when I finally met girls who were interested in me, I lacked the bedroom know-how of other guys my age. I can vividly recall more clumsy attempts at heavy petting than I’d like to and every one of my sexual experiences seemed to result more in disappointment than gratification. When it came time to actually doing the deed, my luck didn’t change. My first “real” girlfriend dumped me because I wasn’t ready to have sex with her. She was older, rebellious and romantic. I was wide-eyed, nervous and too tongue-tied to tell her things were moving too fast. The pressure of it all was overwhelming.

After her, I met my high school sweetheart, who I dated for nearly seven years. She had a beautiful way of making me feel great just for being myself, which did wonders for a young man’s self-esteem and sexual confidence. We had chemistry and she was somewhat adventurous in bed, but I soon became hung up on what we weren’t doing under the covers instead of what we were.

I began questioning my own sexual appetite. Why did I have a schoolgirl fetish? Why did I fantasize about a night of crazy lingerie and spanking? It was hard for me to distinguish the difference between what I wanted and stereotypical male desires, but at a certain point, I panicked about living an entire life and missing out on the wild sex we’re supposed to have. The wild sex we saw in the movies growing up. More than that, I struggled to understand why I cared so much.

When I decided to move across the country to New York, our relationship ended. Afterward I thought, If hometown suburbia wasn’t made for a sexual awakening, then surely New York would do the trick, right? The chance of fulfilling my threesome fantasy still seemed far-fetched, but this was New York, and I was single again. Then I met her.

Halfway through our first date, it became clear that there was a spark between us even though we obviously had little in common. She was cute, charming and a few years younger than me, aka less mature than what I was used to. I was still getting over my breakup, aka not at my emotional best. Still, those differences weren’t deal breakers and soon, we found ourselves in a rhythm of having what all city-dwelling millennials have: casual sex.

On some nights, we’d stay up late to talk about our wants, both in and out of the bedroom. Eventually, threesomes came up. We immediately saw each other’s eyes light up. She mentioned that her roommate might be up for one. It still seemed out of reach—until texts and selfies started getting exchanged. Next came a plan to meet for drinks. And then, just like that, it was on.

I’m not sure if there was a genuine connection between the three of us or just the right amount of whiskey, but we headed in sync to the bedroom without hesitation. The picture-perfect threesome, however, doesn’t include the unsexy reality (and awkward positioning) of cramming three people into a tiny Manhattan bedroom. It didn’t matter though. Everything was exhilarating. We all wanted this. It was the most present I had ever been during a hookup.

Sex between two people usually has a clear stopping point, but when you throw a third person into the mix, there’s no official finish line. She finished before her roommate and having done so, stepped out of room. When she returned, the roommate and I were still going at it. She became visibly jealous and frustrated by the sight of the two of us hooking up without her. Her emotional reaction was big—so big, in fact, it ended with a literal, theatrical storming out. Having a threesome end that dramatically seemed comically tragic. My ultimate fantasy had come crashing down under the weight of logistics.

After the roommate left, I sat alone in my disheveled, post-sex sheets in disbelief as I tried to make sense of what was supposed to be the best sex of my life. I looked around my apartment, at my cheap Ikea furniture, at the crooked, empty white walls and at the stupid bar cart I ended up hating a week after I purchased it. My place was barely furnished. What little stuff I had meant nothing to me. My life now seemed equally as empty. Ending a serious relationship and moving to a new city had a bigger effect on my identity than I had anticipated, and I was grasping at anything to help me find self-assurance as I struggled with being single and lonely in a city as intimidating as New York. A threesome wasn’t it.

I felt guilty for making her feel less desired than her roommate. Meanwhile, she avoided any talks of our future.

Things got awkward between she and I and we eventually stopped seeing each other altogether. I felt guilty for making her feel less desired than her roommate. Meanwhile, she avoided any talks of our future. Instead of having real conversations about you know, feelings, we stuck to the shallow subjects. And casual sex was the main one.

A threesome isn’t an emotionless endeavor. Even with the most innocent of intentions, it’s still a complex sexual experience. Pop culture may fictionalize it as the ultimate notch in a guy’s bedpost, but it carries more weight than that. Any man who’s not in touch with the emotions of all parties involved—including his own—shouldn’t try it. Because an additional person brings an emotional dynamic to the bedroom most of us aren’t used to and can never prepare for.

I fumbled through too many dates and hookups before I realized that escaping reality through love, lust or sex is fleeting. In some instances, it may last longer than a night, but that’s a short-term solution to an unavoidable long-term problem. The issues I struggled with weren’t ever going to be fixed by a physical experience, no matter how wild or kinky.

Casual sex was never going to build up my masculinity or self-esteem; it was merely distracting me from areas of my life I neglected. For years I rejected the emotions of others, whether it was affection or anger, just because I didn’t feel the same or understand what I felt. I spent my entire young adult life disregarding my own emotions so I had a very difficult time accepting those of others. Instead of acknowledging the unrequited feelings of anyone I dated, I selfishly self-manufactured a perspective that framed myself as the victim; just a hapless guy at the mercy of a situation he didn’t want to be a part of.

Strangely, it was the threesome experience—one that is constantly portrayed as a purely physical and hedonistic experience—that forced me to be more mindful of other’s emotions. A partner not outwardly verbalizing their thoughts is not an excuse to ignore cues and play dumb when someone’s feelings suddenly become inconvenient. And doing so in the middle of a threesome, with two women staring at you, will most certainly make you feel like the most inadequate man to walk the earth.

Hooking up with two women at once was fun. That was expected. But checking a threesome off your bucket list won’t bring closure to self-prescribed voids of masculinity. In fact, one could do the opposite and actually make you feel like less of a man, if you end up hurting one, or both of, the women involved. You’re much better off confronting your own emotional shortcomings than attempting to fulfill some horny teenage fantasy—although it probably won’t be as kinky.