Amy was my first girlfriend. I met her in marching band. She was a dancer for the band, in the group known as the “Starlettes.” She had just broken up with her boyfriend of the last ~3 years, and she came on to me, strongly insinuating that I should ask her to prom, which I did. A week later, we started dating.
At prom, her ex-boyfriend raunchily danced with his new girlfriend near us, and Amy responded by twerking on me harder. I got the vague, absurd sense that I was participating in a dance-off. After her ex-boyfriend dropped his girlfriend to the floor—a move which I couldn’t compete with—Amy ran off the dance floor. She was cold to me the rest of the night, and for the next 3 days. She finally broke up with me via text message.
The last I heard about Amy, she was married and had a kid at 19.
Madison was an extremely popular, attractive girl who displayed an unseemly interest in me during the beginning of my junior year. She introduced herself to me by saying that I looked like Joseph Gordon-Levitt, and that Joseph-Gordon Levitt was her favorite actor. She began to hold my hand, call me “cutie,” and say things like, “Isn’t he adorable?” when we hung out with her girlfriends.
One day, she invited herself over my house. We smoked weed. She failed to get high, but I got higher than I’d ever been: a foaming-at-the-mouth type trance that left me babbling and incompetent. After ~30 minutes of me pacing around the room and apologizing, I sat down next to her, aggressively mumbled “I feel like I should kiss you,” and kissed her. We made out for ~5 minutes, during which I visualized myself as an octopus, and my arms, lips, and legs as tentacles. We heard the garage door opening—my mom coming home—and she pulled away from me. She darted out the front door. We never hooked up again.
Yvonne was my second girlfriend. She liked me more than I liked her. Our relationship ended when her dad read an email I sent her about giving me a blowjob. He told her he would kill me if he ever saw me again.
Veena was my third girlfriend and the first girl I ever said “I love you” to. She came from an ultra-traditional Indian background, so relationships were a big taboo in her family—when her parents found out about her previous relationship, they called up her then-boyfriend’s parents and screamed at them.
To get around that, we convinced Veena’s parents that I was gay. I spoke in a lisp when I was around them, wore women’s shoes, and paraded my guy friends as “my boyfriends.” Her parents bought it and left us alone.
Veena was the first girl I ever had sex with, for about ~30 seconds the week before both of us left for college.
I hooked up with Charlotte during my second week of college. She came over and gave me my first blowjob. The next day, she wanted to fuck, but I didn’t have condoms, so she gave me another blowjob. After that night, we texted once or twice, but I wasn’t interested in having sex with her, so we didn’t see each other again.
Olivia was my fourth girlfriend and the second girl I ever said “I love you” to. I was in an on-and-off relationship with her for the last ~2 years. We’re currently not talking so we can “get over each other.” To this day, when I’m feeling alone at night, I’ll pretend my body pillow is her and scream into it, “I love you! And I’ll love you forever and no one can ever replace you.”
This summer, I wrote and recorded a mixtape, “Heartbreak Mane,” about my relationship with Olivia.
This February, I lived in a mansion in Bel-Air for an internship I was doing, and Miley came to one of our parties. She introduced herself as a 17-year-old singer and actress and, after we made out in my room, she showed me a video of her on Youtube that had over 100,000 views. She said she had the same agent as Rihanna. She said she attended the Grammy’s the year before. When I typed her name into Google, things like “Super Bowl Commercial” auto-filled after it.
After our initial hook-up, we went on a date in West Hollywood. We both bought the same book, “In Cold Blood,” and promised we would read it together. We snuck up to a roof, held hands, and made out. She told me that she never had a childhood—she’d been acting since a kid—and that she wanted to be a stripper when she grew up.
I had to leave LA a week afterwards and we haven’t talked since.
La’quisha was a girl I met off OkCupid. She lived in the “hood” in Cleveland (her words, not mine). Her father was a drug dealer and her mom was a drug addict. After taking her to frozen yogurt, we went to my office in Cleveland and made out.
When I dropped her off that night, her neighbor was half-naked and pinned to the ground, being arrested on his lawn. La’quisha ignored it and kissed me goodnight.
Teyana was a girl I met off OkCupid. During our first date, she didn’t seem to have much interest in me, until I showed her my card tricks. She seemed delighted, pulled my hand, and said, “You have to show these to my grandma.” I went over to her grandma’s house, where Teyana lived, and performed magic tricks for them for ~1 hour.
Teyana was cool, we hung out for a couple weeks. I met her brother, a 6’3”, 250-pound half-Hispanic and half-black dude with a teardrop tattoo on his face and $1300 Prada shoes, who was also a drug dealer. He seemed to like me.
On her 18th birthday, I had sex with Teyana in her basement while her grandma was upstairs.
I don’t remember this girl’s name. We met off OkCupid. I went over to her house and was in her bed within ~5 minutes. I couldn’t get hard and I told her it was because I didn’t feel an “emotional connection” with her, when really it was because she wasn’t as attractive as her pictures made her seem. She seemed sad, then asked me if she could at least give me a blowjob. I said that’d be fine.
Afterwards, I sat with my shirt off and showed her my card tricks, which she seemed to really like. As I was leaving, she said “Don’t be a stranger.” I said, “What?” Her cheeks flushed and she said “Never mind, I’m…stupid.” We never talked again.
I deleted my OkCupid account after that.
Wendy was a girl I met off Tinder. We went to a frozen yogurt place named “Harlem Yo.” Afterwards, we went back to my apartment and had a conversation. After she said something about being the best female basketball player in her high school, I was overcome with emotion (I love basketball) and kissed her. We started making out and I was confused by the way she was kissing: she kept her mouth open, like a fish, and I couldn’t tell whether or not she wanted me to put my tongue in it. Five minutes later, she pulled back and said, “I have to go.”
I texted her afterwards, asking her a) if she got home safe (“Yeah”) and b) that I hope she had a good time, to which she never texted me back, leaving me repeatedly checking my phone, alone in bed, embarrassed and a little insecure.