First Year First Times

Freshman fall is full of firsts: first roommates, first B grades, first relationships, and first times. For your eyes only, we hunted through Annenberg, the Yard, and, of course, MIT’s frats to uncover some of the most interesting first-kiss and first-time stories we could find, and put them together for your reading pleasure. Enjoy!

Playhouse Player

This is a classic situation: hooking up with your best friend’s sibling. The Playhouse Player’s first time was with his close friend’s sister, after their high school homecoming. “She brings me to the little playground set up in their backyard, right?” he said. “And we just get down and dirty, bro.”

But things then took a turn for the worse. “While she’s on top of me, her mom opens the backyard door and calls out to her,” he said. “I’m like, I’m going home soon. Don’t worry,” he said. “Like, while P[enis] is in V[agina], you might say.” Unfortunately, it wasn’t the most glamorous of hookups. “We had gotten McDonald’s before, so we had McDonald’s breath,” he continued. “That’s an integral component of it, really.”

Although the Playhouse Player conceded that his partner was probably a better kisser than he was at the time, he claimed he’d improved since. We cannot confirm this fact, but feel free to verify the accuracy of that statement yourself (if you manage to unmask this first-year student).

Timer Terrorist

Many of the best relationships start as friendships! Not this one. “We were talking on and off for basically four years, and we [had] never hooked up,” an unsuspecting freshman explained. Little did she know that she was involved with the Timer Terrorist. “We were sitting in the parking lot, and we knew we were gonna kiss, but we had been friends for so long that it was insanely awkward. So he was like, okay, I’m just going to set a timer, and then I’m going to do it,” she continued.

A timer is perhaps a unique choice, and our interviewee was not a fan. “I was like, ‘Get the fuck out of my car! This is giving middle school,’” our interviewee said. (A countdown also unfortunately did not help the Timer Terrorist achieve his goals.)

“He kept having to reset it because I would start laughing,” our source explained. “He was like, ‘I’m just gonna set another timer, and I’m not gonna tell you when it goes off, and then I’m just gonna kiss you.’” She made him leave, but they hooked up the next day.

“We’re no contact,” she concluded.

Fishy Financier

Our interviewee’s encounter with the Fishy Financier was her first kiss, and it was actually at a Harvard summer program! “There was this guy. He was super cute, he was blonde, and he kissed like a fish. It was kind of bad,” she said. “I didn’t think about him for a while, and then I found out his dad is a billionaire.”

Could you overlook piscine smooches for the promise of financial security? Our interviewee wishes she had. “I did fumble that,” she lamented.

Consent Crusader

This story started with our interviewee and the Consent Crusader lying in bed together. “Our humor really complemented each other, so we were having a really good time,” she said. This first-year described a running joke in her friend group, where her male friends would jokingly touch each other.

“Then there’s this guy that I’m in bed with, and the other guy touches my guy’s butt, and you know,” she said. No, we do not know. “They just touch each other unconsciously, so it’s a running joke.”

“So he leans in, and he’s like, ‘Do you consent?’” Honestly, shoutout to the Consent Crusader. “He’s a respectful queen,” said our interviewee. “He asked for consent multiple times.” Although this is perhaps the bare minimum, the Consent Crusader is who we should aspire to be.

Unfortunately, this relationship did not succeed. “Yesterday I saw him with a girl at 1 a.m.,” she said. “I was also with two other guys.” Maybe they are made for each other.

Hickory DICKory

Hickory DICKory shared with us the juicy details of his first Harvard relationship. “It started off on the first day of orientation,” he said (classic!). “Someone came up to me, basically, and since then we were talking, but this person hates my ass.” That might not seem like the best foundation for a healthy relationship, but who doesn’t love an enemies-to-lovers story? “After that, things worked out, and now I walk to Berg with a collar of hickeys around my neck every day.”

Hickory DICKory took a holistic perspective on his situation. “Experiences are experiences, and you learn and grow from them,” he proclaimed.

We are not entirely sure what he’ll learn from this particular experience, except maybe how to effectively apply color corrector and concealer.

Janitor Juker

Not all romantic first kisses happen in the most romantic of settings. Our interviewee, the Janitor Juker, told us his first-kiss story, which happened at the mall. “I was at a birthday dinner with a few of my friends. Obviously, one of them was the girl that I kissed,” he said. Although we were unsure how a first kiss would naturally happen at someone else’s birthday dinner, Janitor Juker proved that when there’s a will, there’s a way. “I asked if she wanted to go somewhere more private, whatever, and she said yes,” he continued.

There are not many “private” places to make out in the mall, but luckily for the Janitor Juker, he found a solution. “We went into the changing room,” he shared conspiratorially. Our interviewer clarified and asked if the Juker meant the baby-changing room. “Yes, that room,” the Juker replied. They shared a magical first kiss by the diaper tables and breastfeeding supplies. Our Juker did not wow his lover—“she had more experience than I did,” he explained. Unfortunately, their rendezvous was short-lived: “We heard something outside, and the janitor lady was mopping the floor. So we went out quite fast, and then skedaddled that way,” our freshman concluded.

Middle School Meddler

Do not fret about the title; our interviewee was also in middle school when this happened. “We’re like, ‘Okay, let’s go to the park after school,’” he said (a very chic spot for a middle school first date). “We go to this area that has a bunch of trees or whatever, and then we’re just talking, right?”

Unfortunately, relationship drama started early for him. “She was talking about her ex. I forgot what she was saying, but I just remember she was talking about her ex, and I was a little weirded out. And then she kissed me,” he explained. Certainly a less-than-ideal situation to find oneself in. “I should have taken that as the first sign that this girl is crazy.” In her defense, she was 14.

Countdown Coward

This story sounds like an ancient ritual, but it is just a middle school classic. This was our interviewee’s first boyfriend in seventh grade, and they had an impressively long middle-school relationship (two whole weeks!). “We planned after school that we were gonna kiss,” she said. “Both of our friend groups were surrounding us, and then they counted us down, and then we did a peck, and then he ran away.”

Our interviewee wasn’t the biggest fan of the Countdown Coward’s cowardice. “Mind you, he was like 4’11”, and I was like 5’5” at this point.” Friend groups, a height difference, and a corny countdown—this story gives us nostalgia for the good old days.

Texas Chainsaw Man

For some, the Texas Chainsaw Massacre wasn’t just a movie. This first-year student had quite an experience with her first kiss in the great state of Texas, no less. “He ended things because he didn’t want to go any further with a relationship. Like he was still into his ex,” she said.

Our interviewee knew she deserved better, but just couldn’t help getting revenge after finding out. “He was talking with other girls or getting lunch with other girls while we were exclusive, about to be dating.” Fortunately, the Texas Chainsaw Man got what he deserved. “We stole some condoms from Target, and then sprinkled them around his yard and took them out of the wrapper, and put them on his car antenna, and in his mailbox, and under his mat, and just like everywhere,” our source explained.

Although some kind of reaction may have been in order, the Texas Chainsaw Man went to the end and prepared for a massacre. “He found out that me and my friends were playing pickleball the next day at our local pickleball courts, and so he drove drunk to the pickleball courts with a rifle,” she explained. “He showed up to the pickleball courts, hair disheveled, bloodshot eyes, and then whipped out a rifle behind his back.”

We know that some of our readers may like themselves a cowboy, but we assure you there are better people to practice cowgirl with. While some chasing could be construed as romantic, this was not the case. Our interviewee described her harrowing escape: “I just sprinted to my car, and I drove out of the court parking lot as he was following us on foot with the gun, and then fell into a random cul-de-sac and turned off my lights, and we just waited it out there.”

Veritas Voyeur

“My first kiss is boring, because it was when I was a freshman in high school, when I was in my straight era,” said the Veritas Voyeur. Thankfully, he came out of the closet and rewarded us with a juicier story.

“My first time having sex was junior year of high school, so I was not out to my friends and stuff, but I had this guy over with me and my friends, and we were all hanging out. We were in the theater room in my house, which is where there are recliners and stuff.”

The Veritas Voyeur and his partner were ready to hook up, but they were afraid to go anywhere else. “We lowkey waited till our friends were asleep and then did it while they were in the room, and it was so awkward. But it also added to the excitement of it all.” We are not personally fans of voyeurism, but hey, no kink-shaming! “We ended up having the courage to leave the room, and we went to my bedroom, and then it proceeded.”

Whether you have had your first time or not, we hope these stories bring you comfort in knowing not everyone’s experiences are picture-perfect. Regardless of whether your first time involves pickleball or playhouses, we hope you at least get a good story out of it (and that you share it with the Indy)!

Anika Gupta ’30 (anikagupta@college.harvard.edu) and Salma Gheith ’30 (salmagheith@college.harvard.edu) have stories that may or may not be in here!