I Don’t Know How To Play Hard To Get: A Brief History Of Failed Hook-Ups

Seventh grade: Every time his little AIM screen name popped up online (and I kept a careful, obsessive watch) I scrambled to write to him. Michael was two years older, 14 when I was 12. I was desperate to prove my sexual maturity, which I can now acknowledge as disturbing seeing as how even 14 seems way too young for any of those shenanigans. I spelled ‘really’ like ‘relle’ and described a fictional boyfriend as being “so horny that he just wanted to kiss all the time.” Obviously I’d had no real knowledge of the implications of the word ‘horny’ at the time. Eventually he asked me, “Are you obsessed with me?” and I’d been forced to more or less confess. I would later learn he had blocked me on AIM.

Eighth grade: Vince sat next to me in science class. I immediately proposed a game of tic-tac-toe to pass the time, and for the first few weeks, we successfully ignored our teacher and flirted like pros through the use of Xs and Os. One day in November, when I nudged his shoulder and beckoned to the newly formed tic-tac-toe board I’d formed on loose leaf, he’d shrugged and pointed at the chalkboard. I’d lost to science. I spent the rest of the year pouting and entertaining myself with ugly doodles.

Ninth grade: Remember Honesty Box on Facebook? Yeah, well, if you do, you know how this is going to end. I was a freshman and the sophomore guy in my Spanish class, though linguistically challenged, was just so freaking hot. He was perfectly tan and sculpted with a head of floppy brown hair. I decided to confess my love over Honesty Box, and we exchanged a few exhaustive anonymous messages before he point-blank guessed who I was. It became clear he’d caught me staring dreamily every day in class. The rest of the year proved very awkward, as I’m sure you can imagine, but I learned important lessons about subtlety.

Summer before senior year: I spent three weeks at a resort in Los Angeles, and managed to fall in quasi-love with my tennis instructor’s son. We lobbed fluorescent green balls over a net; he matched me in wit and made me smile. He was a pothead and so naturally I smoked more weed that summer than I’d smoked over the whole course of the year. The best part is that he was wounded — we’d have our best conversations sitting with our backs against the chain-link fence surrounding the tennis courts, passing a joint back and forth, while he told me about his broken relationship with his mother, his own personal failures and goals, the anxiety he felt whenever he thought about the future. It was immensely gratifying to break down that wall. After two weeks, he drove me to the Santa Monica beach at sunset. We cuddled on the sand and everything felt perfect, was perfect, except for the way we both faced the ocean, the way his lips weren’t on mine. I might have been high when I said it, but that’s no excuse: “So are you going to kiss me or what?” He’d turned to look at me, startled, and then heaved a frustrated sigh.

“I can’t kiss you,” he told me. “I care about you too much.”

That statement still haunts me, I assure you. I can’t count the number of times I wish I’d never opened my mouth.

College freshman: He was my sophomore neighbor, and when I first saw him saunter through the hall in just his towel, I immediately dismissed every piece of advice I’d ever been given about hallcest. My friend Clara, studying beside me, made an audible gagging sound when he rounded the corner and passed out of sight. “He has the hairiest chest I’ve ever seen!” she said. “Ew.” I thought it was sexy, and he only became sexier when I realized that he was the aloof, quiet, political-minded electric guitarist of my dreams. The peephole on my door became a place of worship. One night in mid-October, I downed four shots and then knocked on his door, inviting him to drink with us. I’m sure I was slurring, which obviously meant we were having fun, so he followed me back into my room as I gave all my friends a goofy grin. It was great to be so close to him, to smell him and touch him, to watch him drink my whiskey without betraying even a wince. After the pregame, and a successful, drunken late night conversation while both draped over armchairs in the lounge, I thought I’d made it in. I texted him on a Friday and a Saturday, asking what he was up to in as casual a manner as I could, and received less-than-enthusiastic responses. I was understandably confused, so I pushed harder. (Less understandable.) As weeks passed, and nothing happened, and my sexual desire grew stronger, I started sending ‘drunk’ texts. Yes, you read that right. I took extra time to construct perfectly misspelled and scandalous text messages. Examples: “Hey therrrrd” and “we should hang out tohether sometimre judst you and meeee!” and finally, “Omg neighbooorr where r uuu toniigfhtt?!?!” I regret to report that he never responded to these, and our interactions in person became less and less frequent. This one makes me the angriest, because there were multiple pieces of evidence that he’d been genuinely interested in the beginning; if I’d just learned to shut the hell up and let him chase me, maybe it would have gotten somewhere.

Bonus failure! I was 16 and he was 24. I had a huge, massive, oozing crush, and yet our relationship seemed to relegate me to the role of ‘sassy friend of a much-younger sister’ (if he’d had a sister). He was a sexy jazz drummer whom I met on a cruise with my family, and I’d spent most of the time on the boat watching him. I added him as a friend on Facebook after we debarked, and initiated almost all conversations for the next three years. I think he was highly amused by me, and our conversations, and perhaps some people would have said his eagerness to talk to me for hours was slightly inappropriate, or pointed towards what inevitably happened. I was suggestive and crossed boundaries in almost every conversation, and I could almost imagine him blushing on the other side of the screen, rushing to make sure his contributions were purely PG.

Suddenly it was senior year and I was 18, attending one of his jazz gigs in New York City, and he was smiling at me over his cymbals, and I was melting, melting, melting, and so triumphant because afterwards he touched my arm and told me how happy he was that I came out to see him, and then after that our conversations, prompted by me, brought him into R-rated territory, and we eventually ended up in bed together. And it was awesome until I started texting him too often, and acting much like a teenager, and he soon lost interest in the concept of a ‘naughty schoolgirl,’ which is all I was to him then, and finally he spent a whole night in my bed this past summer without touching me, and I confronted him in the morning, naked and vulnerable, and he sputtered and couldn’t seem to explain why our purely sexual relationship couldn’t continue, and so it all ended, and he went back to dating people his own age. TC mark

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