I always look forward to Valentine’s Day. I love LOVE, crushes, crafts, chocolate, flowers, letters, pink, and setting a day aside for unabashed cheesiness.
On Valentine’s Day freshman year, I had Covid and my friends FaceTimed me into the Gracie Abrams concert we were all supposed to see together. Sophomore year, I went on a massive group blind date where the couples sat across from each other at one long table, sharing pitchers of margaritas. Last year, I ate pasta at an Italian restaurant with my friends Zack and Andres, surrounded by tables of two.




This week, Dean and I threw our second annual Valentine’s Day party. Our friends exchanged candy and notes like we used to when we were in elementary school. I made a heart-shaped red velvet cake. I have a feeling senior year might end up being my favorite V-day of all…
In celebration of the holiday, I asked my friends to answer some questions on love, dating, and romance at Yale. This letter is split into 6 sections:
Worst College Date
Best College Date
Red Flags
How We Met
Biggest Romantic Crash Out
Most Memorable Valentine’s Day
I had so much fun putting this together, and I hope it’s even more fun to read!!! Happy Valentine’s Day!!! 💌💌💌
First, a little bit about the pool of respondents…
All of them are my friends. 8 out of 20 chose to remain anonymous.
The relationship status breakdown is pretty split.
And most people feel positively about V-day! YAY.
Ok, now we can get into it.
😔 Worst College Date 😔
Jude: Never go on a date with your DFMO. There was this girl I ended up wanting to see again after 'meeting' her on the dance floor of the club. We ended up meeting in New York for a proper date. It was dismal. All I can say is the date ended with her trauma dumping on my couch and refusing to leave my apartment. I was like what the fuq — get out of my house!!
Chela: Ice cream hinge date where he RAN away from me into the library, claiming he had to pee.
Grace: Trying to think of a bad date I've been on at Yale made me realize that no Yale Man ever took me on a date until my current boyfriend halfway through my sophomore year. Maybe that is a worse realization than reminiscing on a bad date. A bad date I had while in college was with a hinge man while I was at home for a summer. He told me I amazed him because I was the first girl he'd ever met with real political opinions. I cannot imagine that is true, I assume he just never asked, cared, or listened. He was 24 years old.
Dean: Thought they were dates. They weren’t.
Anita: I saw this cute guy on the sidewalk and then we passed each other and both looked back (cute) but then he followed me for like three blocks and asked me out (creepy but for some reason I didn’t think of it that way at the moment) and then the date was just a long ass walk where we split a joint and he led me to this part of town I didn’t know and it started getting dark and I thought I was gonna be killed. Then I had to write a paper high as hell when I got home.
Lily: Franklin Dining Hall Dinner (Or the 1701 Concert but I think that was more the person not necessarily the place. But going somewhere where almost everyone you know will be on a date is a bad bad idea. Do NOT recommend.)
Isa: Hinge date in Madrid with a boy from NEW JERSEY. I can’t even be mad.
Iva: We had plans to go to drinks but the guy asked me if I wanted to come watch football with his housemates instead...I said no.
Anonymous Responses:
The date itself wasn't bad. The hook-up on the other hand...
He made a meme attempting to ask me out after I tried ghosting him multiple times.
We went to a coffee shop and he spoke for one hour straight... it was so crazy.
yale boy from an app. i was pretty sure i had strep so i tried to cancel the date but he insisted on walking me to yale health that night, literally sat through my strep test, and then rolled me a personal j (sounds nice?). date was weird (obviously) and nothing happened (obviously) but i texted him after to let him know i didn’t have strep. he replied with four paragraphs about how he really likes me but is in love with his girl best friend and is waiting to see if she breaks up with her long term boyfriend for him, and that he would let me know depending on that outcome if we could see each other again. (what???) i never replied. he texted me a week later saying they did break up but she did not like him back so could we go out again. i think i blocked him.
🤩 Best College Date 🤩
Chela: Probably this one time at a jazz club, though I wasn't sure if it was a date at the time. Or this one date at Rudy's with someone I've known for a long time.
Ellie: Going to L'Orcio (on State Street, very 90s tuscan old Italian stuffy interior but so fun) with Keith in the middle of summer.
Grace: My boyfriend and I go to an aquarium for Valentine's day every year. The first year we did it I made friends with a turtle, he pet a sting ray, and we went to Mystic Pizza. It was quite majestic honestly.
Iva: When we first started seeing each other, Tim and I had a picnic at the top of science hill at sunset.
Dean: On our first date, we went to the Rocky Horror Picture Show with his friends. I felt like I was in The Perks of Being a Wallflower without any of the sad stuff.
Anita: One of my best friends set me up and we went to Anchor Spa - the booth!!!! It was so cute and over time we got closer and closer to each other until we were hella touching. Conversation was wonderful the whole time and then he walked me home and kissed me goodnight at my door <3
Anonymous Responses:
I’m a firm believer in getting a coffee and taking a walk for the first date. I don't know how well it'll work in other spaces, but on a college campus it's great. You can gauge how much you like the person based on how slow you walk, there's never really a shortage of things to talk about if you're outside, and because there's movement it feels like less pressure to come up with something witty or profound on the spot
Went to Indoor farmers market during winter, drank hot dirty chais, snacked on some croissants in the park outside, and talked for a few hours.
Red Flags 🚩🚩🚩
About themselves:
Avoidant and jealous. 😍⭐️
Temper.
I am jealous and possessive, and I assume if someone isn't jealous or possessive that means they don't actually want me.
I’m really picky.
About other people:
Mama's Boys, meanness, pretentiousness, trying to be someone ur not.
Asking about my SAT scores on a first date.
Unfortunately, it's when someone comes on too strong. Or has bad taste.
No hobbies.
No sense of direction, picky eater, and doesn’t know how to vibe/dance at a party.
When there is something that excites you and they are not excited that you are excited
Bad manners! Boooooo
Picky eating habits, posting at the gym, talking when unnecessary.
💗💗💗 HOW WE MET 💗💗💗
Keith and Ellie
Lula and Caroline
Lula: we worked the same shift at Tsai CITY for two years and never spoke… until one day we each had a friend at said shift and finally broke the ice. she said she wanted to get involved in theater and TLDR she started working on two of the shows i was in and we became inseparable. the romantic part became obvious when we were both wing-manning for each other but were canceling our dates to hang out. we kept the relationship sort of secret until the shows were done, and now are about to celebrate our two years! maybe the moral is to never underestimate who you’re sitting across from (at Tsai CITY).
Cami and Amelie
Cami: Was leaving my residential college to walk to a party across campus and ran into a mutual friend and my (now) SO. Made them escort me to the party and, when our mutual friend went SILENT, ended up chatting with my (now) SO the whole way there. Importantly, she did NOT like my attitude upon this first meeting, but I somehow won her over in the end. We also had a run in at a dining hall where I was getting my usual special K red berries cereal with soy milk and she was in line behind me for the same thing. She said “good choice” and swiped up on my story a few days later with another message. 3 or so years later the rest is history!
Iva and Tim
Iva: My friends and I arranged a big group blind date for Valentine's Day in 2023. Tim was supposed to go with one of my friends, but she got a boyfriend in the meantime, so Tim became my date. We sat across from each other at Te Amo Tequila and got very drunk off of margaritas. I was acting a little crazy and Tim was pretty shy...and when we walked home, I thought he was going to kiss me but he didn't. It was a fun date, but neither one of us followed up. Then, in April, Tim texted me asking if I would be his date to Sig Nu crush. We kissed in Sig Nu at 3am and started dating a few weeks later.
Grace and Gavin
Grace: I was the most single I have ever been in my life, and I was scrolling through Instagram and found his page. Not to sound insane, but I kind of decided he was going to be my boyfriend right then (online shopping, boyfriend edition?). I followed him and began to like his Instagram Stories periodically despite never having met him, because in my delusional brain that would make him notice me.
Arden and Chela started calling him my boyfriend when they would see him around campus. At this point he still didn't know I existed. A couple weeks later I was at Arden's birthday party, and out of the blue our mutual friend Zack introduced us. We had a cordial, semi-flirty conversation and then he excused himself because he had to "take care of something." I assumed he just didn't like me (devastating), I assumed he just didn't like me (devastating), but turns out he was holding one of his friend’s stuff because they were about to jump into a koi pond at the party. The speakers got soaked, fish were everywhere, and the party was functionally ruined. I assumed the Boyfriend Gavin saga was over.
Until…the next week we were both at radio initiation, and our other mutual friend Anaiis (who had heard about my crush from Arden) purposely set us up in the same group. We did a scavenger hunt, lowkey fell in love, exchanged numbers, and he invited me to his fraternity party where he was bartending later. At said party, I kept finding myself at the bar to talk to him, despite already being Super Drunk. At one point he caught on, and started putting water in my drinks instead of vodka. I went home, threw up, and woke up the next morning to a text from him asking me out to coffee.
Gavin: I first met Grace at Arden’s birthday party during our sophomore year at Yale. Though I didn’t recall this at the time, Grace had followed me on Instagram and liked some of my stories. Given my general boyish aloofness, this didn’t quite register as interest, though I later found that she had developed a crush because I was friends with someone that her friend was interested in at the time.
But back to Arden’s party. I had come from my social club with a large group. I was introduced to Grace by our mutual friend, Zack. I thought she was really cute (even though she was wearing a Dallas Cowboys shirt - the natural enemies of my team, the Philly Eagles), but I was a bit intimidated. I got the impression that she was a part of the NYC/LA crowd, which I, as a suburban Pennsylvanian, found a little out of reach. We talked briefly, mostly about her point and shoot film camera. Then I got the signal from my friend and simply said, “I’ve got some business to attend to,” and left. I think Grace, justifiably, perceived this as a snub, but I really wanted to see my friend jump into that koi pond. So, he stripped to his boxers, handed me his clothes and shoes, scaled the fence, and jumped into the koi pond. We ran out of the party and didn’t return. The splash from his jump had apparently broken a speaker and the party was effectively ruined.
A week or two later, I was, seemingly by chance (but actually as a direct result of scheming) been placed into the same group as Grace for initiation into WYBC. We really hit it off and she even saw me streak for an (optional) initiation task. I got her number before she left and met up with her later that night at Fence, where I was bartending. She came to the bar an inordinate amount of times, to the point where I started serving her water, which she didn’t seem to notice. At the end of the night, I asked if she wanted to get coffee and she said, “well you have my number, don’t you?” The rest is history.
???
This really cool and cute girl started following me around after class one day...we started going on 15 minute walks in between classes. Then we went on a 2 hour date and now she is my girlfriend.
🚗 Biggest Romantic Crash Out 🚗
Urban Dictionary defines crashing out as “going insane,” “losing all your self control,” or “doing something stupid.”
Chela: I thought that someone I had liked for a long time was seeing a different girl, so I crashed out the hardest of my LIFE and ran 5 miles on the treadmill to The One That Got Away by Katy Perry. Literally until I almost threw up.
Ellie: Finding out about the strip club.
Grace: Honestly I crash out about my relationship once a week probably. I'm not sure if that is a red flag, a green flag, being 23, or a part of my personality I will have to work with forever.
Dean: Flew across the country to see him and got sent back.
Anonymous Responses:
This guy told me I should come over and help him turn up this dead party together, and I immediately responded with “Coming!”
Was supposed to sleep over at a girl's house but I had to cancel day of, her ex slept over that night.
I was close friends with this guy for six months before he told me he wanted a relationship with me. He changed his mind a month later and we never talked again. I was so harrowed that I came out to my sister as bisexual so I’d have something else to worry about.
Looking a boy up on True People Search.
💖 Most Memorable Valentine’s Day 💖
Chela: Gate blind date sophomore year. I was SO NERVOUS. But it was so silly, and we took that iconic group pic before the boys came to meet us in that Branford suite.
Ellie: When Keith took me to a converted barn restaurant in the middle of the Connecticut woods and we were wildly overdressed bc he overestimated the restaurant and then we had to wait 45 minutes for an uber and I thought we'd never get out of those woods.
Lily: My best friend and I made a Valentine's Dinner Reservation and went on a friend date together last year. We even got each other Valentines Day cards and chocolates. It was a fun way to celebrate love in friendships.
Dean: Hosting our vday party lowk…
Andres: I went to dinner with friends last year for Valentines Day. While the pasta was mid, I had a grand ole time.
Isa: Senior year of high school, my long-distance boyfriend at the time (lol) flew down to surprise me for vday. He skipped class and an important event and I had absolutely no idea it was going to happen. There’s a video of me teary-eyed and frozen in disbelief after he showed up to lunch with my friends after school — I think unnecessary, small gestures go a looong way.
Gavin: Our first Valentine’s Day together was supposed to be at Steamed, one of my girlfriend Grace’s favorite restaurants in New Haven. I forget exactly how, but I managed to mess up our reservation. Grace tends to roll with the punches better than I do and took the situation really well. We went to the GHeav near TD and got sandwiches and ice cream while I apologized profusely. We went back to her suite, exchanged gifts, ate an orange in her bed (which appalled me then - I’m not really a food in bed guy), and wound up sock wrestling (look it up) in front of Arden and Chela for a slightly awkward amount of time. I think it only solidified the notion that we were a great fit to them. Altogether a great night that I look back on very fondly now.
Anonymous Responses:
I've never had a real significant other during Valentine's Day. So...it'd have to be those Valentine's boxes in school.
I made a heart-shaped meringue that was supposed to say “Be My Valentine” but I messed it up and the words were reversed. Then my boyfriend and I had a drink making competition and I won with my cherry Negroni. We had the best dinner ever and it was perf.


Love you guys. Have fun today.
oh this is so fun i love reading about other people in love.
"Asking about my SAT scores on a first date." This makes me laugh... what do you expect if you and your date are Yale students. duh????!!!lolll