On May 31, the line outside Dorothy stretched down West Chicago Avenue before wrapping around the corner and down a side street. It was Pride Month Eve, and Chicago’s beloved lesbian cocktail lounge was celebrating with its third annual Gay Prom. Clad in ’80s satin and slip dresses, patrons fretted about whether or not they’d get in (they did), showed off handmade corsages and pregamed with a case of hard seltzers someone had brought and passed around.
Located behind a speakeasy-style door in Chicago’s Ukrainian Village, Dorothy offers an absolute firehose of queer programming. The bar hosts drag, burlesque, comedy, karaoke, a viral open mic that sold out shows within minutes, Silent Book Club, an arm-wrestling tournament against the Chicago Women’s Rugby Club, and holiday season screenings of Carol. But Gay Prom, devised by co-owner Zoe Schor to kick off Pride Month, is among its biggest events of the year, garnering more than 500 RSVPs.
At least a dozen of those in line had been high school students during COVID’s peak, and never got to go to prom. Two now-married couples I spoke with attended their high school proms together. Inside, a special one-night-only prom menu featured drinks like a Waffle House After Party (whiskey, banana liqueur, coffee bitters, cream sherry, Angostura), a Negroni-ish Teacher Chaperone (tequila, Campari, vermouth, mole bitters) and a beer-and-shot special. The crowd went wild whenever DJs Cut-Cuz and Jessi D spun another Lady Gaga track, cramming into the bar’s infamous photobooth to capture an unforgettable night.
The Night by the Numbers
What was the inspiration for Gay Prom at Dorothy, and how has it evolved since its inception?
“My wife Zoe was very passionate about hosting Gay Prom for our first Pride kickoff in 2023. She always says, ‘It’s not a new concept, but it’s an important one.’ It was our first opportunity to celebrate a classic event that takes place well before we are fully formed humans.” —Whitney LaMora (she/her), co-owner
How did you develop the Gay Prom bar menu?
“I was just reminiscing on my own experience being a millennial and going to prom. Hummer Stretch Limo [tequila, lime, dill brine, orange liqueur, agave, jalapeño tincture] came from going to high school and college in Arizona. One of the things we learned dealing with hangovers in the desert is [to hydrate] all the time, so we drank a lot of pickle juice. And then, of course, 2010 to 2012 was the era of everyone taking Hummer limos to prom. I’m a huge Waffle House fan, and when I was at Moneygun, we’d do food-takeover[-themed] cocktails. We had an Olive Garden one and I did a Waffle House one, so I built on that for Waffle House After Party.” —Jasmine Santiago (she/her), bar manager
Tell us about your promposal.
“I got her her favorite strawberry cake from Jewel and asked them to write ‘Prom?’ on it. Then I added the rainbow candles and these two gummy bear couples. I said the ones holding hands were us before prom, and the ones 69-ing were us after prom.” —Lanie (she/her) and Ivane (she/her)
“We’ve made it a tradition to go to Gay Prom, so this is actually our third promposal. They promposed to me first, and then I promposed to them, and then they promposed to me again yesterday, so we just keep going back and forth.”
“We had just gone to see five movies in the Sapphopalooza series at the Music Box, which means you win this special carabiner. I was like, ‘Wait, I think I have a good keychain for you,’ which I had made, asking her to go to prom with me. And then when she flipped it over and saw it, I got down on one knee and pulled out a fake bouquet.”—Rene (she/they) and Max (they/them)
What’s the most rewarding thing about doing an event of this scale at Dorothy?
“It was a record-breaking night for Dorothy, but at one point, we all looked around and were like, ‘Oh my god, it’s so chill in here.’ We’re doing a lot, and there are a lot of people in here having fun, and we’re making the money, but we all felt super at ease. And then the feedback from the guests, being able to see people come in dressed beautifully, and watching them dance and have fun. I saw a photo strip the next morning when I came in for my shift, and the person had taken their blazer off in the photobooth. They were completely topless, and I was like, I love that you had such a good time and were able to capture that moment!” —Santiago
How was your Gay Prom night?
“I kind of liked that it was almost a little bit cheesy, with the balloons and the rainbows, playing into the nostalgia of it all, because that’s what my prom was like! For me, I’m obviously femme, so going to prom in high school, I didn’t have to really dress any differently. But I know it was really important for my partner, who is butch, to wear a bowtie and an Oxford shirt and go with their girlfriend to prom. And it felt really special to me to go with someone I’m romantic with and not my gay best friend.” —Greer
“The music was really good, so many prom throwbacks. At one point, [my partner Max and I] danced to Whitney Houston’s ‘I Wanna Dance With Somebody.’ It feels kind of silly that this was the song we had such a romantic moment to, because there were [also] slow dances. But during this one, we turned to each other like, ‘I don’t think I’ve ever actually danced to this song with someone who actually loves me?’ [Laughs.] So that was our big romantic moment.” —Rene
“Once we made our way through the crowd to the bar, just seeing everyone in their true form, whatever they wanted to wear, however they wanted to show up—I’m a very emotional person, so it gave me such a nice, warm, fuzzy feeling of safety. It’s very cheesy, but it’s true. It felt like magic! I had this crazy movie flashback in my head of like, everyone at the prom how they presented in high school, whatever that might have been, and in most cases, it was probably totally different, right? Seeing everyone now look so happy, and smiling, and loving on their dates, romantic or not—just the safety they felt to act however they wanted made me feel so nice. It really did feel like prom... except we were allowed to drink!” —Lanie
