Reflections On The Men I’ve Slept With

I’ll always remember Tom as the most influential force in my life, the most transformative. He was there for me through everything. He appeared when I was at the lowest point of my life. I had just gone to college, I hated it there, and I believed that I was too crazy, too neurotic, too sad to be loved. And there he was. He loved me for everything I was and he made me better every day. We had one of the most honest, open, and genuine relationships any two people could ever have. Our sex life was crazy. We tried everything. We made a sex tape. We had photo shoots. We booked expensive hotel rooms in exotic places behind our parents’ backs and made sure the entire floor heard us having sex. We made each other feel wanted. I had always wanted my first to be special. He was special and so much more. He is the one constant thing in my life that I know will never become a regret.

I slept with John because I thought it would make him love me. We had dated in high school, when I believed that he would be the one. I believed that I would never love anyone that much again. I believed he broke up with me because he wanted to experience all the stereotypical college adventures of partying and drinking and hooking up. I believed that if I could make myself one of those things, if I could become a casual friend with benefits, I would somehow fit into his life again. And I believed that in between the drowsy post-sex conversations as we were falling asleep or the small exchanges in the early morning as we refused to get out of bed, we would fall back in love again. But ultimately, the more desperately I tried to fit into his life, the less I did. I never got any glimpses of honesty. Instead, he just thought of me as a slut that he could take advantage of, and I learned that sex is a weapon with an uncontrollable recoil.

I sleep with Tom whenever I need to feel attractive again. We’ve been best friends since middle school. Out of everyone I’ve met, he’s one of the people I admire and respect the most. Perhaps sleeping with him assures me that I have his approval, and it makes me feel like I’m doing okay in life.

It seems hurtful that I think of Young as the relationship I never wanted. He was the first person that made me think critically about a future with someone. He was funny, he thought I was funny, and we always had a great time together. In the past, that had always been enough. I had believed that love was about simplicity, about finding someone that made you happy from day to day. But while I was Young, I wanted more. I thought about whether his values and beliefs were ones that I wanted to commit to a life with, and more importantly, whether those were the values and beliefs I wanted my children emulating. I broke up with him when I realized that the answer was no.

Jamie was a roller coaster. He gave me the high I was seeking, that feeling of falling unreasonably, illogically head over heels in love. I didn’t care if it wasn’t real and I didn’t care if it would never last. I had spent the last two years having only casual, detached, one-night-stands. I made it clear to everyone I hooked up with that I wasn’t interested in their call in the morning or seeing them on a date afterwards. I went to every hook-up with less than zero expectations. I felt cynical and broken and worst of all, I felt like a cliché, and I needed to know that I was still capable of being vulnerable. I manipulated my schedule in all sorts of ways to spend time with him. I checked my phone every 15 minutes to see if he had texted me back. Every time we hooked up, I believed that it was the beginning of some new amazing relationship. It was the happiest I had ever let myself be since my breakup with Tom. And when things fell apart, I let myself be sad. I drank irresponsibly, I cried myself to sleep, I sat in my room and avoided my thesis and watched House of Cards. I don’t think it’s fair to say that Jamie was a jerk. Our circumstances were unfortunate, but he never lied or did anything dishonest. He just didn’t know the role he was playing in my life. After proving I could have sex without emotion, he assured me that I was still capable of attaching my full spectrum of emotions back to sex. I’d be lying if I said he didn’t hurt me deeply or that I wasn’t still hurt right now. But the silver lining is that I feel good knowing I’m still human.

I think of Nick as my initiation to city life. I had just started graduate school and I had just decided that I hated it. My college was a liberal arts school, so I always had no trouble finding people who were interested in finance, business, literature, and politics. I was constantly surrounded by people who didn’t care about their classes as much as they cared about their dance shows, their clubs, student government, and their start-ups. But suddenly, I was thrust into this environment where everyone cared about engineering and research and didn’t seem to care about much else. Every study break or school-sponsored social event involved people talking about the same work I had gone to the study break to get away from. I was used to being the most hard-working, research-obsessed person in college. Suddenly, amongst all these graduate students who were so much more accomplished and worked so much harder, I felt like a slacker and I wasn’t at all motivated to compete. All I could think about was how I worked so hard to get here, only to end up miserable. It felt like everyone had come to terms with growing up and I was Peter Pan looking for Neverland. So I got on the hook-up app, Tinder, set up a date with a random guy at a bar, went home with him, had sex with him, left in the morning and never saw him again. Nick was really just my way of saying “screw you” to grad school.