Illustration by Minna

Illustration by Minna

There’s this tree in a park by the house where I grew up that’s scarred multiple times with my initials. From the ages of 10 through 14, every time I developed a new crush, I would carve my initials and his into the bark with a little + between them. I feel awful about this, because not only was I wounding the tree, I was doing it under false pretenses. I didn’t even like four of the six boys whose initials I scratched into that trunk. I told my friends I did, and I wanted it to be true, so much so that I went to that park by myself to vandalize that poor tree. I’m not sure if I thought this act of professing my love would make me actually fall in love, or if I was afraid my friends would find out I was lying and then I could point to the tree and sayz, “Would I go that far if I didn’t actually want Sam Kennedy* to be my boyfriend?”

But I didn’t want Sam Kennedy to be my boyfriend. In fifth grade, I didn’t want anyone to be my boyfriend. I still thought boys were gross, mean, annoying, or all of the above. I did not understand why all the other girls in my class suddenly had this need to be paired off Ken-and-Barbie style with those icky/cruel/obnoxious creatures, but they did, and I didn’t want anyone to think something was “wrong” with me. I wanted to be as giddy and carefree as the girls with crushes and boyfriends seemed to be, so I faked it, and this poor tree bore the brunt of my lies.

In eighth grade, when a boy with chin-length wavy brown hair and an adorable smile caught my eye—and proved to be funny and kind, defending me against gym class bullies—I finally understood the appeal of having a boyfriend. I wanted to be around this guy constantly, to go to dances, to make out. When I thought about doing them with him, those things didn’t seem gross anymore—they seemed fascinating. But I was too shy to make a move, so I just crushed on him for over a year and went through total agony when he asked another girl to the eighth grade graduation dance.

After that heartbreak, I restricted my crushes to guys I saw in the hall, juniors and seniors whose names I didn’t even know. Meanwhile, my friends were getting into real romances. My best friend from grade school was having actual sex with her boyfriend. I had always been at the top of my class academically, and I did not like this new feeling of being at the bottom of the social heap. I felt like I was seriously behind and that I would never catch up. So I lied.

My sophomore year, there was a freshman named Derek who told my friend Robin that he thought I was “hot.” I wished I could return the sentiment, but I found him more adorable than sexy. At that point, though, no one had ever openly admitted to like-liking me, and who knew if it would ever happen again, so I told Robin to give him my number. Derek and I were soon a couple, and I discovered that there was a lot to like about him: He had great taste in music, and he introduced me to a couple of metal bands I hadn’t heard of before. He could be serious, and he could also be funnier than just about anyone I knew. We had great phone conversations. I really, really liked him…as a friend.

But I wanted a boyfriend. I thought I needed one. And I believed that if I made it official between me and Derek, I would magically develop romantic feelings for him—even if that had never worked when I carved the initials of my fifth-grade “crushes” into that tree. I’m not the only girl who settled for a boyfriend like this even though it felt like it at the time. In fact, most of my girlfriends in college admitted to going out with or even having sex with someone just to figure it out, see what the big deal was, or like me, to keep up with their friends. We were all in this imaginary social competition that none of us wanted to be in and as a result, a lot of us missed out on the beautiful awkwardness of having first dates and first kisses with people we actually had feelings for. I really wish I’d cared more about myself than other people’s perceptions of me, because first romances should be, you know, romantic.

Derek was my first kiss. It was after a group date with Robin and Derek’s friend Will. We were in the backseat of Will’s car, and as we were pulling up in front of my house, Derek leaned over and laid one on me. His mouth was a lot wetter than the first kisses I had daydreamed about with my eighth grade hallway crushes, and it tasted like an ashtray. I kept kissing him for the next couple of weeks, hoping that some spark would develop. Everyone but Derek could tell I was faking it; Robin said I looked sad when I should be happy, and I was definitely forcing my smiles around him. Will told me I had to break up with Derek before I really hurt him. But that happened anyway; when I finally got up the nerve to break up with Derek, I hooked up with one of his friends a few days later. It turned out I was capable of crushing on someone after all—just not Derek. I never started a relationship under false pretenses again—but in my early 20s I did something even worse.

I met Simon when I was 17. I’d graduated from high school a semester early and moved to Madison, Wisconsin, with a friend for the summer—my last summer before college—so this could have been the perfect summer fling. There were no parents and no rules, so we did some pretty dangerous and stupid things, like inviting drunk guys we’d just met at goth clubs back to our place.

Simon looked like a tall, skinny, red-haired Robert Smith, and so naturally I was instantly attracted to him. We invited him over and he promptly passed out in our hallway, but eventually he came to my room and asked if we could “just cuddle.” That was all we did, which made me like him more because in addition to being hot, he seemed respectful and sweet. And he was. He was also 23 and a party boy who got me into any club I wanted to go to and took me out to drink in graveyards and to skinny-dip in lakes. Being around him was a constant thrill. Whenever he touched me, my insides did Gabby Douglas–style acrobatics. I hated being away from him, and spent most of my time at his place. It was everything I’d hoped to feel with Derek.

Our “summer fling” lasted eight years, half of which were downright awful. Simon and I also fed each other’s self-destructive habits. He was a big drinker when I met him and I quickly became one. We romanticized William Burroughs and Hunter S. Thompson and convinced ourselves that heavy intoxication was key to being artists. By 21, I realized that I’d spiraled out of control, and I decided to move back home to Chicago to live with my mother and go back to college. This is a point when Simon and I definitely should have broken up, but instead he came with me. I think I just wasn’t ready to let go yet—destructive as our relationship got, it always had that intensely comforting “let’s just cuddle” side to it. The self-destructive part was not as comfortable, though, and eventually I grew tired of it. I knew I needed to get away from him, I just literally didn’t know how to do it. Derek was the only guy I’d ever broken up with, and I’d only done it because my friends made me. It ended horribly, with me losing Derek as a friend, other people thinking I was a bitch, and me feeling like one. And at this point I was pretty fragile. I was working through some of my issues with depression and drinking, and I felt emotionally dependent on Simon. I didn’t love him anymore; I was using him as a crutch.

By the time we moved to Chicago, he and I were fighting all the time. We fought about the music I liked (“too screamy,” he said), how much he was still drinking (partying was starting to get old for me), and especially about money (he lost his job and quickly spent down his savings buying clothes, electronics, and booze while I paid all the bills). My mom, my best friend, and my therapist spent the next two years urging me to break up with Simon, and a big part of me wanted to, but I didn’t. I cried when I told my mom that I was miserable, and I knew he was an alcoholic and our relationship was unhealthy but I felt like we needed each other. We were miserable together but happy to not be alone. When I broke up with Derek he got drunk and drove Will’s car into a tree; he was OK, but Will told me it was my fault, that I’d hurt Derek and sent him on that downward spiral. I was afraid to hurt Simon like that, and afraid of being alone.

I wish I could say that I eventually found the strength to break up with him, but I didn’t. He went home to Wisconsin one weekend and left me a voicemail saying he didn’t want to come back. I sobbed for an hour, but I went to bed feeling relieved. When I got up the next morning, he called to say he had second thoughts. I told him I didn’t. I felt much lighter than I had in years. I had gotten so used to waking up with a weight on my chest, the kind of feeling I’d had when I had to go to a job or a class I didn’t like, except this was constant, and of my own choosing. Once it was lifted, the idea of being crushed by it again was a hell of a lot scarier than being alone.

That phrase “fake it till you make it” was in my head all the time during my relationships with Derek and Simon, but I thought it meant that if I faked feelings long enough it would make them real. As it turned out, “making it” actually meant discovering my role in these relationships, and figuring out what I really wanted beyond just having a boyfriend. I do wish that when I’d started to get an inkling—when Derek and I kissed and I knew we’d never have chemistry and when I knew deep down that I wanted to go back to school without Simon—I’d been brave enough to stop faking. That’s the biggest danger about faking: It starts to seem so much easier than real life, when the truth is that my real life would have been so much easier if I hadn’t spent so much time faking it.

I did so much more in the eight months after I broke up with Simon than I did during the eight years we were together—I finished a novel and landed a literary agent, I went to school in Los Angeles for a semester, and I had my first real and lasting romance. None of this would have been possible while I was faking my way through my love life. I found that lying to yourself in one area of your life tends to hold you back in all of them, but if you break that pattern in one area it takes a weight off your chest, and you just feel different. You feel like you can do anything you truly want. ♦

* All names have been changed to protect the innocent.