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‘It’s a Date!’ skips the small talk, goes straight for the funny business

Comedian Jaylene Tran during a performance of "It's a Date!" on Oct. 27 at Turtle Swamp Brewery in Jamaica Plain.Jenna Triest

Jaylene Tran was certain of two things: her schedule as a stand-up comic was leading her to burnout, and dating these days is just as exhausting.

So, the Harvard University student got creative. She said, “Instead of chasing stage time, how about creating stage time for myself?”

Thus was born “It’s a Date!,” Tran’s interactive comedy-dating show, where audience members engage in activities that make typical icebreakers much more amusing. As Tran saw it, a shared sense of humor is a vital ingredient for compatibility. The comedian produced her first performance of “It’s a Date!” in February, and now hosts shows in downtown Boston, Jamaica Plain, Roslindale, and Brookline.


“My goal is to have a show in every neighborhood and slowly become the dark mother of dating for Boston,” Tran said.

During each performance, Tran rotates between different themes, and audience members are tasked with an assignment that determines who they may get paired with that night. In one of her most popular shows, the venue walls are lined with memes ranging from photos of wholesome comics to screenshots of dark Tweets. Audience members write their names on the meme they find funny, and Tran plays matchmaker — calling pairs with similar taste in memes up onto stage and grilling them about their love lives.

“Alright,” she said during a recent gig, “this person and this person both find this [expletive] up Tweet funny. Let’s bring ‘em up here and find out what’s wrong with them!”

Tran created this show with the intent of easing the stress and anxiety that comes with dating in your twenties and thirties. But as a live show, sometimes, life takes over: once she invited an audience member to talk about a recent breakup, only to find out that the ex in question was there — a surprise.


“People love to see the unscripted, the unexpected,” she explained. “If I can’t see it coming, they can’t see it coming either. That’s the best part of the show.”

At Tran’s dating show, everyone can be involved. Spectators are encouraged to ask the spotlighted daters questions and, as Tran explained, the weirder the questions, the better. It might get awkward, but the show’s spontaneity is designed to cut down on the (sometimes equally awkward) small talk that comes with mingling singles.

“It’s no longer ‘hi, what do you do?’ We actually get to what’s more important,” she said — turn-offs, turn-ons, and other secrets that might not be revealed on a first date. The shared, unique experience is the important part, she added, and if someone ends up with a phone number at the end of the night, that’s an extra bonus.

The in-person opportunity to meet someone new, for some singles, is also a welcome reprieve from dating apps and online dating.

“Dating apps just are not doing it for me right now. I’m much more of an in-person kind of person,” said Hillary Lynch, a high school teacher, after Tran’s Oct. 27 show at Turtle Swamp Brewing in Jamaica Plain.

Audience member Jin Hao Lin agreed that dating apps aren’t “really serious.” “If people are looking for a relationship, this kind of event would work,” Lin added.

Tran said she is always researching new ways to enhance her performances. For now, she’s taking it one show at a time. If people are laughing and bonding, Tran believes she’s done her job.


“Yeah, we’re laughing, but we’re not laughing at each other,” Tran said. “We’re laughing with each other, because we know that we have all been there.”

It’s a Date! at Hideout Comedy, Thursday, 8 p.m., White Bull Tavern, 1 Union St., Boston. Tickets $20, eventbrite.com. For more upcoming performances, follow Tran on Instagram @jaylene.tran.