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Age nineteen - "Hot Patootie - Bless My Soul" from The Rocky Horror Picture Show
In college, I met a theater major in the dining hall and we bonded over mutual vegetarianism and our love of William S. Burroughs. She was more outgoing than I was, and I feared I'd lose her if we spent another Saturday night watching movies in my dorm room and talking. Come Halloween, she planned to go to a midnight Rocky Horror screening in a Columbia outfit she'had assembled last year. I also wanted to go in costume, but if she was Columbia and we were going as a pair, my choices were Frank or Eddie, and I wasn't brave enough to do Frank. After getting my Eddie costume in order, we sashayed around her dorm room to "Hot Patootie," a song celebrating what I was attempting: a cool guy goes out and gets laid. There were ten people total at the screening; we were the only ones in costume. She soon stopped calling and took up with a pierced guy who DJ'ed a local house/industrial night.
Age twenty - "Everybody Here Wants You," Jeff Buckley
I was on a road trip with a female friend when we stopped for the night at her mom's house in the Philly suburbs. At about two in the morning, I was laying on a hide-a-bed in her basement when she just sorta jumped into bed with me. Nothing like that had happened to me before. She ran her fingers through my hair and said, "God, you're sexy, in a Jeff Buckley way." Even today, when I mentally prepare myself for a first date, I try to think of myself as a Jeff Buckley type: brooding and passionate beneath the obvious nice-guy label. Thank you, Mr. Buckley, for everything you did for emotionally intense young white men with average bodies.
Age twenty-one - "Closer," Nine Inch Nails
My second major relationship was with A, a bookish girl with a mischievous smile. Unlike C, she didn't have much of a CD collection, just a few '90s albums leftover from high school. I assumed her lack of a multi-generational, multi-genre, carefully alphabetized music library like mine meant A didn’t understand how useful songs were in coloring certain moments. She proved me wrong one night by ripping my clothes off, tying me to a chair with two belts and giving me a lap dance to "Closer." It's a memory I still recall often, if you know what I mean. "Closer" is the best song about sex ever written: Trent Reznor equates carnal lust with tossing one's self worth at the altar of an uncaring god, which hits the nail right on the head.
Age twenty-four, "Just Like You," Roxy Music
During my quarter-life crisis, a suicide-hotline operator called a squad of cops and paramedics to force me into a mental hospital. You get to know people intimately quickly in a psych ward, thanks to therapy, downtime, and the general emotional mushiness of the environment. I got close to a dental hygienist who was drying out from a manic episode. She gave me her number when she was released. Two days later, I turned on my recently-returned Discman, which resumed playing Roxy Music's Stranded. "I know it sounds crazy / But what can I do / I've fallen head over heels, over you," Bryan Ferry sang in "Just Like You." Years later, long after the relationship blew up due to the to-be-expected erratic behavior on both our parts, that song still makes me want laugh and/or cry.
Age twenty-nine, "Wouldn't It Be Nice?," The Beach Boys
I met J through a dating website. She had just earned her MFA and moved back in with her parents. We wound up in bed together on our second date. At about eleven p.m., she said she had to get home so her parents wouldn't worry. "Think of an excuse to be away for a night," I said, "so I can cook you breakfast while you wear one of my long t-shirts." She smiled and said, "Soon, I’ll have a place of my own and we can hang out every night." Then she paused. "God," she said, "this is like that Beach Boys song, ‘Wouldn't It Be Nice?’ and we are way too old for that." I queued up the song as she got dressed. The next day, she sent me a rambling email about how sex on the second date broke some rule of behavior she had set for herself, and that she'd had fun with me but couldn't see me again. We're not too old for it, J, at least not for the sentiment beneath it: the yearning to finally have something lasting and substantive. That's a feeling you can relate to if you a chaste teenager in 1966 tired of just holding hands and pecking cheeks or a long-time OKCupid user in 2013 jaded by one-night stands and frustrated by false starts.