A Brief History of Men I May Have Loved (And Who Didn’t Love—or Even Like—Me Back)

This essay is also featured on the My Week In Tinder Valentine’s Day special episode, which you can also listen to on PodOmatic, iTunes, or Stitcher.

(Note: Nearly all names have been changed. This is not to protect the men I am writing about, but to protect myself from further past, present, or future humiliation.)

Wanting what I can’t have has been a recurrent theme in my life. I’ve wanted my curly hair to be straight; I’ve wanted my practically translucent skin to be just a shade or two darker (read: not vampiric); I’ve wanted my neuroses to seem charming, not terrifying.

My romantic history is not free from this curse: I am unrequited love’s bitch.

I started a new school in sixth grade and almost immediately developed a crush on Bryce Horowitz, the most popular boy in class. At age nine, I was diagnosed with scoliosis and had to wear a back-brace for twenty-three hours a day. It wasn’t anything like the one Lisa Kudrow dons in the flashback scenes of Romy and Michele’s High School Reunion. But it’s hard enough to be a twelve-year-old girl, let alone one who has to buy clothes two sizes too big to hide the plastic corset she wears to correct her S-shaped spine. I wasn’t shy about my back-brace—quite the opposite. I made sure everyone knew about it as soon as possible. I would tell boys to punch me in the stomach, taunting them, “Go on, I can take it.” I guess I learned the importance of owning the things that made you different from everyone else at a young age. In the ten years I wore a back-brace, only one person ever made fun of me. And I responded by punching him in the stomach.

On my twelfth birthday, my parents let me go to school without my back-brace. I wore a pink Juicy Couture top and jeans that fit. My mom straightened my hair. I looked like all the other girls. In homeroom, Bryce came over, wished me a happy birthday, side-hugged me, then exclaimed, “You’re not wearing your brace! High-five!” I was smitten.

I spent most sleepovers with my girlfriends whispering late into the night about how I wanted so badly for Bryce to be my boyfriend. At a boy-girl birthday party later that year, the DJ (what, your classmates’ sixth grade birthday parties weren’t at rented out clubs in midtown Manhattan?) organized some game for the prepubescent attendees in which every boy had to ask a girl to dance whenever he said “snowball.” After seven or eight turns, Bryce looked at me and sighed, “Alright, Densen. Let’s do this.” I was so love-struck that I didn’t realize he decidedly did not want to dance with me.

Despite receiving clear signals that he wasn’t interested, my infatuation continued well into seventh grade. I was elated to receive an invitation to his Bar Mitzvah, although I didn’t attend because it was on the same day of another classmate’s Bat Mitzvah that my group of friends was attending instead of Bryce’s. I was distraught, but I wasn’t going to fly solo to synagogue to watch Bryce stumble through his Torah portion. Can you imagine?

Later that year, I definitively learned that Bryce did not feel the same way about me. My friend Rachel signed into her AIM account from my computer during a sleepover. She IM’d Bryce.

Rachel: Do you like Kate?

Bryce: No.

Rachel: So you don’t like-like her?

Bryce: I don’t like her as a person.

I don’t know if I was more mortified or heartbroken.

Despite attending a relatively small school, I managed to avoid Bryce until my senior year, at which point his popularity had already peaked. He was still one of the cool kids, but didn’t have as pervasive an influence. One day toward the end of the hellscape that was my high school experience, I was at my locker. Which was weird, because although the locker had been mine for four years, I never used it, let alone knew that Bryce’s was just a few lockers down. It was a free period, and the halls were quiet. Bryce appeared at his locker and spent several minutes struggling to open it. He looked at me, shrugged, and sheepishly offered, “Ugh, these lockers, right?” I was shocked to hear his voice, more shocked that he was specifically addressing me even though I was the only person in the vicinity. I blinked a few times and replied, “Are you actually speaking to me?” Emboldened (and now slightly embarrassed) by my bitchy reply, I walked away before he could respond.

I was over Bryce by the end of seventh grade but didn’t fancy myself in love with anyone for a few years. I had crushes that were generally unrequited. There was one boy who did return my shy, early pubescent affections, but by eleventh grade he had come out and was president of my high school’s chapter of the Gay Straight Alliance. This is also a recurrent theme in my life, but that’s a different story.

My next love after Bryce was during my junior year of high school: Andrew Boyd. He was a charming and good-looking goofball senior, and in my playwriting class. Andrew loved making me uncomfortable. More important: I loved letting Andrew make me feel uncomfortable. He would go out of his way to touch me: he sat behind me in class one day and started to massage my shoulders. Even though I not only welcomed this attention but also reveled in it, my response was to dramatically freeze up, then turn around and glare at him. He stalked me in the library. Or I stalked him. It was mutual stalking. He once lingered while I was making copies for a history project at the Xerox machines, distracting me, making me laugh. I would freak out to my friends about his flirting, histrionically declaring that it’s not normal for someone who’s practically a stranger to touch your elbow, then your shoulder, then try to play with your hair before you shove him and walk away. But internally? I loved every minute of his attention. A classmate in our playwriting class took it upon herself to write a scene that addressed the “Unresolved Sexual Tension” between me and Andrew. We were both cast in the scene, which called for a kiss. Neither of us had the balls to go through with it.

Andrew had a serious girlfriend who went to a different school. A very talented dancer girlfriend whom I had gone to a performing arts sleepaway camp with for three years. You know you’re a product of the NYC prep school circuit when these too-close-for-comfort degrees of separation are a regular occurrence. I tried to seem nonplussed when I heard that Andrew was seeing someone. But I’ve never excelled at hiding my feelings. I have what kinder acquaintances have described as an “expressive face.” The less kind have said, “Do you purposely roll your eyes when you think someone’s an idiot, or is it just an automatic response? Like a facial tick or something.” It was no surprise that despite the aloof attitude I tried to exude, my friends knew I was devastated to learn that Andrew wasn’t single.

The fact that Andrew was in a relationship made me question whether I had misinterpreted his interest in me. One Saturday night, I was sitting with my friend Sarah on the steps of her apartment building, chatting after an evening of underage drinking at bars that were too fancy to care about carding. I was smoking a cigarette—a habit I had picked up a few months prior because Audrey Hepburn smokes in Breakfast at Tiffany’s and I thought of myself as a 21st century teenage version of Holly Golightly. (In case it wasn’t already clear: I was not well liked in high school.) Sarah and I were slightly buzzed and chatting, I was smoking, and a cab stopped short toward the end of the block. The door opened and Andrew buoyantly exited and ran towards us. He apparently lived around the corner from Sarah. How did I not know he lived around the corner from Sarah? In hindsight, not having that knowledge was probably a good thing. If I had known, I am confident that I would have practically moved into Sarah’s bedroom and set up a stalker basecamp, replete with binoculars.

It’s been over a decade since Andrew elatedly (Sarah confirmed this adverb as appropriate at the time) ran down an Upper West Side block to talk to me. It was the first, and only, time I saw him outside of school. I don’t remember the content of our conversation, but I know I tried to play it cool and act peeved to see him after midnight with no adult supervision. I think we can all safely agree that the reality was the exact opposite. I had forgotten about that moment until I decided to write this essay. In hindsight, it remains one of the most rom-com experiences of my life and I wish more like it had followed.

On the last day of our playwriting class, a friend of Andrew’s approached me and said, “Don’t worry. He’s just as much in love with you as you are with him.” I rolled my eyes and walked away.

Andrew graduated and I never saw him again. He went to the same prestigious and reputably competitive liberal arts college as my close friend Matt, who was two years ahead of me in school. I’d occasionally ask Matt if he ever saw Andrew around campus. Matt said that he did sometimes see Andrew, who was usually riding a bike or walking alongside the bike so he could talk to his new girlfriend.

I’ve checked in on Andrew throughout the years via Facebook. He went on to get some sort of science-related graduate degree and co-founded a start-up. He’s married and mostly bald.

I won’t lie: I started my senior year looking for Andrew in the halls and quietly missing him, or perhaps more accurately, missing what could have been. But I soon found a new object of obsession: Tim Goldberg.

Tim and I had identical schedules but were, two-dimensionally speaking, polar opposites. He was a popular jock who told fart jokes and I was the artsy girl who dressed in all black, thought she was smarter than everyone else, and made snide comments. One day, he came into our AP Spanish Literature class twirling his lacrosse stick. Our teacher narrowed her eyes, “Tim, would you please stop playing with that?” “Well,” I offered, “you know what Freud would say.” (Fun fact: saying things like this out loud is not how you make friends in high school.) Halfway through the class period, I commented on the phallic symbolism of the titular matriarch’s cane in The House of Bernarda Alba. Tim counteracted my earlier remark, “Gee, Kate. You keep talking about penises. Anything you want to share?”

Tim and I talked a lot on AIM. I would message him under the guise of having a question about our AP Calculus homework. Then we would just chat. For hours. But he didn’t talk to me in school other than to tease, sometimes gently, but it was mostly mean-spirited. At the time, I thought this was just the hormonally influenced post-pubescent equivalent of a third grader pulling the hair of the girl he liked. I once said we could get coffee or something outside of school. I don’t remember his exact response, but it was something like, “People like you and people like me can’t be friends.” Tim was never interested in me. In hindsight, Tim barely tolerated me. And I get it. I was a piece of work in high school. And only high school. I graduated and immediately became a delightful person who radiates sunshine and rainbows. (Things that are lies!)

During my freshman year at a small liberal arts college upstate, I met Joe Kahn, a soccer player from Maine who looked like a poster boy for the Aryan race. He lived on my hall and was basically Tim 2.0, but we hung out together. In public! In front of other people!

We bickered, but good-naturedly. (Obviously, over-consumption of romantic comedies during my formative years led me to believe that bickering was the universal sign of unresolved sexual tension.) We were friends. Friends who became even friendlier when drunk but never too friendly. I vaguely remember my annoying him about something one night and his saying something like, “Kate, if you don’t stop doing that, I will not not not not hook up with you.” I don’t remember the exact number of double negatives and whether they added up to his hooking up with me or not. But the fact that he thought about doing so was (and remains) apparent.

The attraction was mutual. Or, at least mutual enough that other people picked up on it. We were watching a movie one day and throwing pieces of popcorn at each other when Joe’s roommate said, “Would you guys just go ahead a make out already?” We both laughed nervously and I immediately left. A month later, I found out that Joe had a girlfriend whom he had been with for two years. I started liking him even more. Until they broke up.

After my freshman year, I transferred to a school in the city. I didn’t have anything to do over the summer, so I started taking classes so I could better acclimate once the fall semester began. One of my classes was Intro to Creative Writing. I was 20 years old, and at that point, I still thought I was going to pen the next Great American Novel. I have since realized that I just wrote one semi-decent short story during my first undergraduate semester and coasted on it throughout a series of creative writing classes. The summer course was small—only eight students. And I almost immediately fell in love with Tom Smith, a cute, broody intellectual from Maine who chose to sit next to me on the first day of class.

(Sidebar: I am now wholeheartedly wary of men from Maine. I admit this is an unreasonable bias, but the fact is that it’s almost a decade later and it is difficult for me to not immediately dismiss a potential romantic interest if he is from Maine. If you are reading this and are from or live in Maine, my deepest apologies. Blame Joe and Tom. I certainly do.)

I would run into Tom at Starbucks every morning before class. But he always seemed wrapped up in his own head, so my attempts to make eye contact and smile at him were futile. So, I crushed on Tom from an emotional distance even though we literally sat next to each other for three hours a day, four days a week. When I received my classmates’ feedback on my first workshop piece, I casually flipped to Tom’s comments: Your sentences are, more often than not, beautiful to read. Be still, my pseudo-cerebral, would-be novelist heart. (Apparently, if you want me to fall in love with you, you just have to realize that I am an insecure creative and praise my work. Do that, and I’m basically yours.)

Despite the effusive and beautifully written comments about my beautifully constructed sentences, Tom remained aloof and difficult to engage. I realized I would have to make the first move. So, one day during break, I placed a post-it note on his book while he was out of the classroom: If you ever want to hang out sometime, here’s my number. – Kate. He called me that weekend. (The Post-It of 2008 remains one of the slickest things I have ever done.)

We hung out a few times during the summer semester—we started unofficially meeting at the Starbucks we had each independently frequented before class. We took walks between morning and afternoon classes. We got drinks one night. And then he went back to Maine for the rest of the summer and I didn’t hear from him, not even after the Fall semester began.

In late September, I saw him crossing the street. I texted him a few hours later (because that’s how long it took me to compose the text): I-think-I-saw-you-crossing-Broadway-earlier-and-hey-how-was-the-rest-of-your-summer? He texted back and we made plans to get coffee one night across the street from my dorm. The coffee shop was closing, so we went back to my dorm room. I sat on my bed. He sat in my desk chair. He talked about how he hated his roommates: one of them had a rat-face and the other had accidentally taken and then lost his keys so he couldn’t get into his room. He kept coming back to the fact that he needed to get back to his dorm while his roommates were still awake so he could get into his room. But he made no moves to leave. About 30 minutes after he left, I had what I thought was an epiphany: Was he saying all that stuff about his roommates so I’d invite him to stay??? So, naturally, I texted him just that. And never heard from him again. Lesson: some men have a very low threshold for ballsiness in women.

In hindsight, I internalized Tom’s lack of response to my painfully straightforward text as a rejection. It not only heightened my already present insecurities, but also manifested as immediate suspicion of any man who expressed even a nugget of interest in me.

In February of my junior year, my friend Remy and I went to a Fountains of Wayne concert at Joe’s Pub. (Sigh. I used to be so cool.) The band invited a few audience members to join them on stage to play supplemental instruments for “Hey Julie.” I remember thinking that the guy playing the maracas was cute. After the concert, Remy and I were standing outside figuring out what to do next when Maracas Man and his friend emerged. I pointed them out to Remy who misunderstood me and thought that Maracas Man was an actual member of Fountains of Wayne. Before I could clarify, Remy was asking Maracas Man, whose actual name we soon learned was Sam Newton, to sign her shirt. We invited Sam and his friend to get drinks with us, but they declined. And that was that.

Until Sam found me on Facebook, an act that impressed me because I was (and am) notoriously difficult to find on Facebook. This, I learned, was the downside of being such good friends with someone named Remy. (I’m just kidding. Remy, I know you’re reading this and I have so much love for you. And a huge retroactive thank you for putting up with me through what followed.)

Several hours of Facebook-stalking later, Remy and I learned that Sam was an Ivy League educated 27-year-old with myriad creative interests. He was a full-fledged adult who had graduated from law school and paid his own rent. I lived in a dorm my parents paid for and had been legally drinking for fewer than six months. But women mature faster than men, right? Sam’s Facebook messages were the highlights of my days. We liked the same music, books, and movies, so we were obviously meant to be. Because clearly, an appreciation of Ben Folds even when he isn’t “cool” anymore is a super solid foundation for a romantic relationship. Sam invited me over to watch Jumanji with him and his roommates. I declined. I’m still not sure why, but my best guess is that I was scared. About a year after meeting him, I invited him to some dorm party that he showed up to after work. He was incredibly out of place in his suit and tie. And while I thought we would be so good for each other, that we seemed perfect together on paper, I realized that he was very much an adult, and I had a lot of growing up to do.

I kept Sam in my periphery since first meeting him in 2009—I think part of me was waiting to be “ready” or “adult enough” to date him. We recently met for after-work drinks at a bar in midtown. We had an easy rapport and still shared similar interests, so I naturally started imagining us together just as I did when I was twenty-one. But it was different, because I was an adult too and the age difference was no longer awkward—it was normal. I tried to convince myself that I wasn’t interested in Sam anymore, that he was just a good person to be friends with. But I was disappointed when he didn’t come to my birthday party, and I realized that despite trying not to be, I was into him. We intermittently texted or chatted on Facebook. He sent me a sweaty post-jog selfie, and I texted at least five of my friends to ask what they thought that meant. The fact that I always initiated the interactions should have been clue enough that he didn’t feel the same way. Sometimes a sweaty selfie is just a sweaty selfie.

We met a month or so later for a last-minute drink and he invited a friend of his to join us. Sam talked about how he’d slept with almost one-hundred women, and that he was planning to go all out, whatever that meant, for the lucky hundredth caller. His friend left, and Sam said, “Well, I’m going to go fuck my paralegal.” Slightly stunned, I nodded, put on my coat, then asked, “You’re not interested in me at all, are you?” He responded, “Sexually? No.” I apparently needed more clarification, so I said, “But you were.” He seemed uncomfortable, but replied, “A long time ago.” I looked at him, still a bit puzzled, and said, “Huh. Okay. Well, I’ll stop trying then,” and left the bar. I haven’t spoken to Sam since. I don’t know why it took my explicitly asking him about his interest in me (or lack thereof) to accept it. I do know that I probably dodged a bullet by not going over to his apartment to “watch Jumanji” all those years ago. And even though Sam is still older than I am, I no longer think that I’m the one who has a lot of growing up to do.

I can’t help but see the parallel between directly asking Sam, “You’re not interested in me at all, are you?” and having my friend Rachel ask Bryce over AIM, “Do you like Kate?” Maybe the relationship between the two events is more perpendicular than parallel, but there’s an undeniable similarity between my insecurities as an awkward preteen girl and my insecurities as an almost 30-year-old woman. Regardless of the differences surrounding the question, the crux is the same. And I’m hopeful that looking Sam in the eye and directly confirming that he wasn’t interested signifies the end of my tendency to emotionally invest in men who, more often than not, don’t even like, let alone love, me back.