I read Bridget Jones’s Diary at the age of sixteen, I thought I had found my salvation. By my senior year in high school, I felt like I had already had my share of crappy dating experiences, from the kid I dated freshman year who insisted on always wearing his varsity jacket when he had lettered in marching band, to the junior spring dance where I thought a secret admirer had bought me a ticket, only to publicly find out that it was an administrative glitch and I still owed $10 to get in. These experiences could have sucked, except, as I learned from all my pop-culture single role models, from the hapless Bridget to the outwardly glamorous and inwardly neurotic Sex and the City ladies, dates should suck. It seemed to me, that the more intelligent and self-possessed a chick-lit heroine, the less she can navigate traditional boy-meets-girl setups. But that’s all part of her imperious charm, until she finds the guy who falls in love with her winsome neuroses.
I ended up going to an all-female college, which further complicated my ideas about dating. There, as confused and lonely freshmen, my suitemates and I bonded through our mutual obsession with the frat guys from a college twenty minutes away. We often drove there just to bump into one of them coming out of class. After doing this for several months, I scored a date with one of them. I saw this as proof that that my ridiculously over-the-top persistence was effective, and I wanted to prolong the situation. When we ended the evening at his apartment, I explained to him that I was a virgin. “But I really want you to fuck me,” I said, as I wiggled out of my jeans, already imagining how jealous my suitemates would be. “Okay,” he said, visibly weirded out.
I never heard from him again, but I didn’t care. In the chick-lit novel I was crafting in my mind, I was the fuck-’em-all girl who didn’t follow the rules. If I didn’t try to date, or deliberately sabotaged the process, I couldn’t fail. None of my friends would know how terrified I was of interacting with guys. Because I didn’t measure up to my friends in terms of attractiveness, I believed that fucking was the only way to keep myself on the same page.
When I graduated, I kept my circle of female friends from college, worked with all women and lived with two female roommates. It was hard not to objectify men when I only interacted with them as hookups. Going out on weekends, not knowing where I would wake up, made me feel adventurous. I loved everything associated with fucking — the danger, the uncertainty, a story to tell the girls. Occasionally, a guy would ask for my number. I’d let the message go to voicemail, then delete it after playing it aloud for my friends.
Sometimes, I would go on actual dates, usually with a friend of a friend, always with a sense of obligation. Actual dating — being picked up at my apartment, going to a restaurant that was never quite right, trading life stories — seemed so banal. With each date, I felt the stakes get higher. Fucking on the first date meant he wouldn’t call again, so I wouldn’t have to veer from my well-rehearsed script.
“I can’t believe it just took one beer to make you come home with me!” one guy said the next morning with a mix of amazement and self-congratulation. I just smiled. We hooked up every Saturday or Sunday for a few months, but we were never dating. Instead, I would end up at his apartment after midnight, usually when one or both of us were drunk. We would sleep together, then have a rambling conversation about our lives, which didn’t intersect anywhere except his bed. When one of these late-night discussions revealed that he was actively dating other girls, I was surprised by how upset I became.
My friend Melissa, who conducts her dates with unflinching rigidity (she won’t even stay for a drink with a guy if she doesn’t see a three-date-minimum potential), was appalled at my haphazard approach to men.
“You’re not supposed to sleep with them right away!” she said, as if explaining something revelatory. “They ‘ll never be interested in you.” That wasn’t the point. I hadn’t wanted them to be interested in me. I didn’t want to worry about their opinions. Instead, I wanted to call the shots until a guy came along who would totally and effortlessly understand me. I hated how much my casual-hookup guy had become that ideal in my mind. For the first time in my life, I admitted to myself that I was actually seeking a relationship.
Which was exactly what my friends had been seeking that whole time, reading He’s Just Not That Into You and sending covert text messages to decipher their dates’ behavior. When a friend successfully navigated the first few dates — the point when sex and weird tics were discussed — I’d feel a small tug of betrayal. I signed up for a bunch of dating sites and begrudgingly promised myself I wouldn’t fuck on a first date. I tried to think positively about going out with the guys whose responses flooded my inbox: it was a reason to dress up, an excuse to live outside my $15-an-hour, post-collegiate budget, something to talk about the next day. Still, I hated how a guy would insist on walking me back to my apartment, when I knew I could always get there, by myself, at any time of the night. I hated when they called the next day and I would feel obligated to call them back, and I would feel anxious whenever I saw one of their e-mails. Unlike hooking up, dating — and actively seeking a long-term connection — made me feel trapped.
It was only when I’d dissect the evening with friends that I would again feel empowered and fun instead of lonely, awkward and panicked. I gave each date a nickname — a guy with questionable hygiene became Furry-Teeth Guy, the pseudo-musician was Mr. Glam Folk Rocker, the hippie activist who lived with six roommates in a loft with bedrooms separated by office dividers became the I Heart Brooklyn Boy. Naming my dates, then excoriating them, made me feel a sense of control. Yes, I hadn’t found anyone, but there was something so wrong with everyone.
One night, I invited a few friends to stop at a bar where I was on a first date. I wanted them to see the live version of what I would always recap, and I had no qualms about using him as a prop. The guy was an aspiring actor and bartender in his mid-twenties. When I flirtatiously asked him what his favorite drink was, he said Sex on the Beach and asked if I’d heard of it.
The next day, my friends laid into me. “At one point, you were making out with him, then you would turn to me, tell me how lame he was and roll your eyes,” Melissa said, exasperated. “I don’t know what to do with you.”
At that point, I didn’t know what to do with me, either. Presented with an unattractive date, I could chalk the evening up to disappointment, or I could turn it into an experience. Of course, I chose the latter. Making out wasn’t fucking, but at least it made me feel something. It turned me back into the imperious single girl, the one was above dating and didn’t need to impress a man.
Ultimately, I am terrified. I really shouldn’t responsibly be allowed to have an online-dating profile. I know it’s time to grow up, stop being hypercritical and just enter the dating pool, with all its clichés and absolute disappointments. And I’m trying. But it’s hard to know where to begin. Pop culture has made wacky, convoluted attempts to meet men seem like a staple of the twentysomething single girl’s life — so much that my therapist once recommended I borrow my parents’ dog from New Jersey for a day and bring it in the park for use as a conversation starter.
While I haven’t resorted to crossing state lines with my parent’s sixty-pound labradoodle, I have agreed to tag along with Melissa to one of her speed-dating events. I initiate conversations with guys at my triathlon-training sessions. Sometimes, I even return phone calls.
Or at least that’s what I’ll admit to my friends. Last week, I went out with a guy from a networking event for impromptu drinks after work. In true romantic-comedy fashion, the heel of my shoe got stuck in the pavement, and I had to lean down to pull it out just as he walked in. We went to the bar, where he followed my lead and ordered a bright pink, prickly-pear margarita. Right then, it was as if the laugh track in my mind was cued, except no one was there to watch. It didn’t seem to be a cute story; it just depressed the hell out of me. We were in the middle of a conversation about his childhood pets when I cut the date short.
Instead of going home, I called my former fuck buddy, holding my breath until he answered. Hey. Just so you know, I’m just calling you because I’m in your neighborhood. So . . . wanna hang out? I let the pause linger, so he knew exactly what I meant. In the silence, I realized my mind wasn’t working overtime to generate some monologue or overarching meaning to my actions. I wasn’t trying to create a story, salvage a scene or use him as an understudy to my failed date. Instead, it was simple: all I wanted was no-rules, no-meaning sex.
He told me to come over. I hailed a cab and ran into the ladies’ room of the Starbucks on his corner, slipping off my thong under my skirt and stuffing it in my purse. I felt the same way I did in high school, when I always wanted to smoke a cigarette after being forced to sit through a dinner party with my parents and their friends. I wanted to be bad and wild, not worried about doing things correctly. When he let me in, he said “Hi” as he took my top off, and at that moment, it was as if I’d stepped out of my self-imposed girl-about-town dramedy and could just be the fucked-up, neurotic, confused chick that just needs space in between all the contrived romantic encounters to find some sort of connection.
This article originally appeared in Nerve’s True Stories.