“Our prom was in D.C. on a boat on the Potomac. In the limo on the way there I rapped all of Biggie’s ‘Dead Wrong’ to try to impress my date. Afterwards we went back to my house and watched Minority Report. Pretty sick evening overall.” —Joe Bernstein
“It doesn’t show my full outfit and omg this is all so awkward. Help. But seriously, I went with one of my best friends, Ben and it was the most fun.” ” —Chelsea Marshall
“I wore a top hat, white gloves, a tailcoat, and a monocle to prom. I don’t usually get embarrassed about many things, especially things from high school or middle school or whatever, but this is still something I am deeply regretful over.” —Dave Stopera
“I NEVER wore my hair up, and still don’t…but had to for PROM for some reason. My dress was a semi-backless dress, light blue, rhinestone detail. (My date was late, didn’t even make the group shot. He played baseball and their game ran over. :/)” —Chris Ritter
“So, my date came all the way from Missouri to Ohio go to my senior prom with me. (Isn’t she a beaut?) To her dismay, I dressed like a fool and thought my sideburns were cool. They weren’t… and I paid for that when she refused to dance with me all night because she ‘had a boyfriend’ back in Missouri. We still keep in contact to this day and have an arranged marriage at 33 if we both don’t have significant others at that time.” —Austin Hunt
“Here are two pics. The first is me and my date, standing outside the prom venue. Remember when baby’s breath in your updo with two front curls was so kewl???
The second is this girl Debbie who was also on prom committee (yes, I was on the prom committee) and we realized after describing our dresses to each other that we’d bought the same one from the same boutique. We were friends and we thought it was funny, whatevz. She looked better in it because her arms were super toned and she was athletic — this was before I knew what tricep dips were — BUT I made my appearance in it first since she was on the softball team and they had a game the same night as prom, so… I felt pretty cool about that.” —Emmy Favilla
“So a few of my friends and I realized something a few weeks before high school ended, something I now describe as YOPO (You Only Prom Once). We consulted with our dates on what dress they’d be wearing, went to Men’s Wearhouse and each got ties and vests to match their dresses. What we didn’t tell them was we were going to also be donning top hats, white gloves, and canes. In hindsight, we probably should have told them… but either way it was a hit. Everyone wanted to take pictures with us and our dates and it was a great party.” —Jacob Fischler
“This is my prom date Amanda and I. We dated on and off during high school. I went to an all-boys prep school and I met her at a friend’s band’s concert a few years before this. Our prom night was a lot of fun. We split a limo with all our friends and I wore a tux put together from like other tuxedo parts. Amanda, on the other hand, looked really nice.
Weird thing, though, about about my prom experience — I ended up going to a total of like, five proms. I had friends that were girls in other schools and a bunch of them needed a date, so I kept tagging along. I got REALLY good at doing the ‘Cotton-Eyed Joe’ and now permanently know all the words to Journey’s ‘Don’t Stop Believin’.’ Also I can tell you to always get the chicken francese. It won’t fill you and usually is the least gross of all prom food.” —Ryan Broderick
“Fun fact: Jennifer Aniston wore my prom dress in an episode of Friends.” —Deena Shanker
“We don’t call it ‘prom,’ but we have formals in Australia. This is at my Year 10 formal, which I attended with my first serious boyfriend — who is now my husband! I was so annoyed when we didn’t win ‘best couple’ on the night, and decided it must have been rigged because the mum of one of the winners counted the votes.
Leading up to the formal, I searched and searched but couldn’t find a dress I liked (that I could afford), so I ended up wearing a dress my mum had worn to my uncle’s wedding. It was hot pink and beaded and I actually loved it.” —Jenna Guillaume
“My date’s dress was pretty colorful so I stuck with a silver vest and a light silver tie. Why the light silver tie? I have no idea. Maybe something to do with color gradient? That’s a thing, right? Anyway, I thought it was a good look and it was a super fun night.” —Logan Rhoades
“I wore a vintage cocktail wrap dress, gold jewelry and leopard print heels. We went to prom in our friend’s ’70s ‘shag’ wagon and blasted T-Rex’s ‘Children of the Revolution’ as we rolled up to Navy Pier where our prom was being held.” —Macey Foronda
“I’m wearing a black tulle BCBG dress that went to my knees. I had on the cutest black ballet slippers but you can’t see them. For my hair appointment I brought a picture of Summer Roberts at The SnO.C. dance and asked my stylist to do the best she could to copy it exactly.” —Katie Heaney
“My original senior prom date ditched me last minute for another girl (ah, high school), so I asked a friend who I had just met fairly recently in drama club to be my date. I initially didn’t even want to go to prom anymore but we ended up having a great time and are still friends to this day, which makes me happy in retrospect. I bought the dress online (don’t remember where) and it was super flowy and a brighter color than I was used to wearing, but given that 60% of my prom motivation was to look confident despite having to scramble to find a date, I’d say it was a solid choice.” —Julia Pugachevsky
“I’m wearing a dress I found at the mall because I’m from the Midwest and in the Midwest people shop at malls (full disclosure, my mom actually found the dress for me — she’s really awesome). My high school prom is always outside in June so everyone wears short dresses to prevent you from overheating. I really liked my dress, until I found my cousin Amanda (pictured) at the dance and then I liked her dress more.” —Emily Orley
“I wore a vintage dress I had bought a few months earlier from a small shop in Philadelphia. When I saw it, I had nothing to wear it to but knew I had to have it. When prom time rolled around, I was so pumped. It had a high-low lace overlay and is still pretty much the coolest dress I have ever worn. I wore vintage clip-on earrings and plain pointy toe black satin pumps. My boyfriend at the time wanted to wear all-white patent shoes and I forbade it because I thought they were hideous. Those were the shoes that he ended up picking and I remember all night being like, why the heck does he think these white shiny shoes are cool.” —Lili Salzberg
“This was my third and final prom dress, and I’m glad it’s the only one I have a picture of because they definitely got less embarrassing each time. It had one of those open backs where the thin straps criss-crossed all the way down, which my 18-year-old self thought was awesome and borderline scandalous (my 25-year-old self agrees, to be honest).
The actual prom was mediocre, but beforehand we went to this famous, fancy bar at the Raffles Hotel — I grew up in Singapore, I didn’t just have a crazy destination prom — where they invented the Singapore Sling. We each ordered one and agreed they were too sweet and not very good. But, the bar itself is this gorgeous colonial-style room, and their gimmick is that the bar peanuts are unshelled and you just crack them open and throw the shells on the floor. I must have had more than just the one cocktail, because the combination of peanut shells and heels almost took me down on the way out. That’s what I think of when I see this dress.” —Christine Byrne
“I wore a green, satin column dress. I remember being taller than my date, so I wore flats but you can’t tell by the pic. I went to prom as a sophomore in 2006. I remember it being really fun, but it seemed almost like a wedding. It was in a ballroom at a hotel and as an after event we went to the Indiana dunes to hang out by the beach.” —Hannah Gregg
“I am wearing a beautiful blue dress from Caché. I’ve never fallen in love with an item of clothing at first sight the way I fell for this dress and I still own it (wore it to the army ball in college my senior year). Unfortunately, my hair, in retrospect, was not worthy of the dress and was actually a hot mess. First and only time I’ve gotten a professional updo in my 25 years of life. I remember the night as being incredibly fun. My friends and I got ready together and rented a limo to take us and our dates to prom. Lots of dancing at the actual prom, followed by IHOP in our dresses.” —Ellie Hall
“I was really proud of my dress because it was this shimmery black fabric that had two cutouts on the sides of the waist, which you can kind of see. You can tell it’s the early 2000s because of my 1) Y-necklace! and 2) chunky blonde highlights.” —Jessica Misener
“I wore a rented white tux (way before Matthew McConaughey and Jared Leto) and drank too much peach schnapps. I remember slow dancing to Garth Brooks and then I woke up on the floor of a Holiday Inn room.” —Dorsey Shaw
“My favorite prom dress: It was long and flowy and only $110 from Von Maur, which was a STEAL. My best memory of prom was when the cardboard Eiffel Tower fell on top of us all while we were dancing.” —Lara Parker
“For my prom, I wore a Betsey Johnson dress I got from the nearest Betsey Johnson outlet, and felt super cool and fashionable for wearing it. That same week, How I Met Your Mother aired an episode that was about its characters crashing a prom. In it, my prom dress was used as an example of a totally UNCOOL and UNSEXY dress that modern-day teens would NEVER wear to prom. Luckily I did not hear about this till years later. I still think my dress was awesome, though!” —Mariane Uribe
“I spent way to much money on my non-refundable dress at a little boutique because I thought it would be unique and different. A week after I bought it, I found basically the same dress at Express for a fraction of the price. Ah, well.” —Kimberly Wang