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People Remember Their Most Excruciating 'Promposal' Experiences

"One time someone asked me by writing it on a Taco Bell taco wrapper, but I gave the taco away to someone else and didn't see it."
Photo by Sean Locke via Stocksy

Prom: A night where many teens bid their high school careers and their virginities goodbye, while others, like myself, spend the night dodging kisses by "going to the bathroom" during slow songs. For teens who attend, it's not a night easily forgotten—even if they wish it would be.

Perhaps the most interesting thing about prom isn't prom itself but the elaborate courtship ritual surrounding the event. I, for one, came home to a JFK cardboard cutout in my room (I had an unhealthy obsession with our criminally handsome 35th president at the time), with a paper quote bubble taped to his face asking me to the dance. It featured some kind of play on words—maybe "Ask not what your country can do for you, ask if you'll go to prom with Jake." I don't remember.


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In retrospect, this is weird. In the moment, however, the gesture seemed thoughtful at best and like a lot of work at least, which is apparently all it took to get me to agree to attend prom with a guy I was not interested in. In light of prom season, and honor in the memory of JFK, I decided to ask people about their strangest, most extravagant, and/or biggest missteps with promposals. During my quest, an Australian friend messaged me to say "the US is so extra w prom" [sic]. After hearing the accounts below, I must say that my Australian friend is not wrong.


Five years ago, I planned the cringiest proposal for my then-girlfriend. I completely stole the scene from 10 Things I Hate About You where Heath Ledger (R.I.P.) sings "Can't Take My Eyes Off Of You" by Frankie Valli and the Four Seasons. He completely makes a fool of himself in the bleachers of his high school football field, and that's exactly how embarrassing I wanted my promposal to be. I was super nervous because I never got to rehearse and I was singing totally out of key for the first half, but once the music hit I started to feel more comfortable. I'd probably do something like this again, but I'd do an actual run-through beforehand, and I envision myself appearing out of nowhere via a helicopter.

You can watch John's promposal here.


One date attempted to ask me by trying to write "Prom?" with the potatoes on his plate at Village Inn. He was rearranging them in front of our friends but they were shaking their heads at him like No, don't do it. He kept trying to ask me throughout the night and I was so oblivious. It ended with, when I was getting out of the car, [him] saying, "Hey, you dropped a dollar." Then I was like, "Nah, I don't have cash on me." He insisted I dropped a dollar so I was like, Okay, and he had just written "Prom?" on the dollar—because I had missed the potato thing.

One date attempted to ask me by trying to write "Prom?" with the potatoes on his plate at Village Inn.



I think there were like two days left before my senior prom, and my boyfriend hadn't asked me to prom yet because I think things had been weird between us, but anyway, I knew it was coming soon because it had to. All my friends took me to lunch at this place where they had a patio with tables right next to the street. We were sitting and eating when, all of a sudden, a pickup truck pulls up and music starts playing, and a bunch of his friends jumped out of the pickup truck and started doing a little synchronized dance.

Then, my boyfriend stood up in the back of the truck, and turned around, and did a trust fall into all of his friends' arms (they were on the ground). His friends then made a tunnel, and he ran through, went right up to me with a flower and said, "Will you go to prom with me?" I said yes, everyone was staring at us, and then, without a word, they all silently got into the truck and drove away.


So this would have been our senior prom in, like, 2010, and I had my eye on asking this one particular cute sophomore. Maybe it was nervousness—probably ended up being the laziness—but I was doing a really great job at procrastinating figuring out a creative way to ask her to prom. I had multiple ideas running through my head, like making a sign, doing that car paint on her car, or ordering a pizza to her house with the toppings spelling out "Prom."

I procrastinated so badly that it came down to one of the last weeks I had, and I knew I had to act. One night it was raining very badly and I was still trying to figure out how to ask her with just a few days left when I came up with what I thought at the time was a genius idea: I could pretend that I wrote her a message on the driveway of her house in sidewalk chalk asking her to prom. Then, the next day, I would show up at school asking for an answer, obviously knowing that the rain had "washed away" the message, when in fact I never actually went and did the deed!


So without writing any message at all, I showed up to school the next day and feigned complete innocence asking if she got my sidewalk chalk message (which of course was never there in the first place). She said no, and I told her that I wrote her a message asking her to prom in chalk and the rain must have washed it away! We both concluded that the rain must have washed it away, and I acted embarrassed and upset. She totally went along with it and didn't doubt for a second. Everything went along smoothly after that, and we ended up having a great prom. She doesn't know to this day that I never wrote the message.


One time someone asked me by writing it on a Taco Bell taco wrapper, but I gave the taco away to someone else and didn't see it. It was really awkward. Another time, I knew this guy was gonna ask me to prom and he brought me a bouquet of carrots because I love baby carrots, and then we went to Teriyaki and he meant to have the waiter write "Prom?" in teriyaki sauce, but the waiter forgot so we went through the whole date and he never asked me and then, after it was over, he texted me and asked if I wanted to go.


I invited one of my best guy friends from another high school to my prom junior year, and he got me a snap bracelet corsage, not realizing I loved snap bracelets. So when he asked me to his own prom a couple weeks later, he had taken 50 snap bracelets, written Taylor Swift lyrics all over them (we both loved Tay at that point), and handed them to me as a bouquet with a card that said, "Make it snappy—prom's coming."

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I was asked by fro yo, like he spelt out "Prom?" with the toppings, but I ate the whole thing so I didn't see it, and then the guy had to sit there waiting for me to say something while I ate it. He eventually had to be like "Ruby… did you not see the note?" I said no, and then he just had to ask me.