Some say Vermont is BYOB: The second B stands for “bae.” With a small and aging population, the Green Mountains can be an inhospitable place for people looking for love. And according to Burlington sex educator and comedian Jenna Emerson, dating app culture actually makes the search more complicated.
“The biggest thing I hear is that people are on [dating apps] who are not genuinely looking for a relationship,” she said in a recent video chat. Rather, she continued, many turn to the likes of Hinge or Tinder for a quick self-esteem boost or to stave off boredom. “No one’s actually feeling good about themselves or wanting to meet up,” she said. “It’s just a horrible disaster.”
So last fall, she unveiled “Sex With Jenna: Dating Show,” a live, seated event inspired by the classic TV show “The Dating Game.” On Friday, February 6, she’ll bring it to the Higher Ground Showcase Lounge in South Burlington. (The event is sold out, but tickets will be available soon for her next installment on Thursday, April 23, at Vermont Comedy Club in Burlington.)
Emerson’s show operates just like “The Dating Game,” albeit heavily queer-centered. A person sits on one side of a partition and asks questions of three people on the other side, then chooses one to go out with. Sounds simple, but Emerson explained that a lot of thought and work happens before anyone sets foot onstage.
After seeking applicants through social media and word of mouth, she distributes a questionnaire to find out what people are looking for. Aside from the basics — name, age, gender, sexual orientation, preferred relationship structure — Emerson also makes sure to ask potential contestants for names of people with whom they don’t want to be matched. (Vermont’s a small world, after all.) Then, with help from two nonpartisan out-of-state friends, she groups potential matches.
Who gets to be in the power position as the one doing the choosing at the end of the game? Emerson considers the broad power dynamics of app culture.
Who gets to be in the power position as the one doing the choosing at the end of the game? Emerson considers the broad power dynamics of app culture. For instance, studies have shown that Black women, Asian men and other marginalized identities consistently receive less attention, fewer responses and more rejection than other groups.
“I want to give [power] to people who [don’t] necessarily have a harder time but just face more discrimination,” Emerson said.
Emerson has seen all the dating shows, from “The Dating Game” to “Singled Out” to “Love Is Blind.” She finds that they frequently play up rejection, something she’s actively working against.
“We’re here to celebrate vulnerability,” she said.
Though no one will be pulled up onstage from the crowd, there’s a bit of audience participation. Each show begins with a brief exercise to get people in the spirit of togetherness. This week, Emerson will lead a discussion about first kisses. Furthermore, audience members can potentially walk away with their own romantic connection. Attendees are given a “flirt card” at entry, upon which they can write a flirty message to anyone who catches their eye (provided that person consented to receiving them, also decided upon entry).
In Vermont, Emerson said, “There is more of a wholesome desire to meet people organically, in person.” ➆
This article appears in Love & Marriage Issue • 2026.
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