Arts & Entertainment
3 min

Trans hook-up tips from Sunny Drake

The Toronto playwright dishes on dating triumphs and failures in his new Buddies show No Strings Attached

Sunny Drake brings his solo show No Strings Attached to Buddies in Bad Times Theatre.  Credit: Tania Anderson

Falling for your best friend is practically a queer rite of passage. So much so, that an unrequited crush catalyzed at a slumber party or Boy Scout weekend is nearly a genre unto itself. In the case of Sunny Drake, longing for his BFF isn’t the subject of his solo show No Strings (Attached). But the heartbreak induced by the experience still served to spark his creative process.

The show began as a 20-minute excerpt eight years ago. In the wake of being rejected by a friend who didn’t love him back, it served as an artistic antidote to being shot down. After he was free from the clutches of emotional ruin, he shelved the project, returning to it two years ago with the idea of developing a full-length work.

NSA centres on Jimmy, a guy who’s furious with his ex. Done with being hurt, he decides to join RAA: Romance-Aholics Anonymous. Staged like a support group, the show positions the audience as fellow attendees. On the surface, it might sound like a thinly veiled autobiographical pity party. But despite its personal elements and ominous tone, NSA is both a work of fiction and a comedy.

Drake’s life since his failed romance has shaped both his optimism and sense of humour about his past tragedies. Happily hitched for seven years to writer/activist/Feminist Porn Awards-founder Chanelle Gallant, his belief in true love has been renewed.

That’s not to say he’s given up on sleeping around. Firmly polyamorous, the couple maintain multiple partners in addition to their pairing. Though he’s historically dated mostly women, Drake’s current extracurricular engagements tend to be with men.

“Among some queer women there’s a real veneration of trans men and we can have a lot of privilege in those circles,” he says. “Within cis gay men’s circles, I feel like people can be a lot more threatened by the prospect of hooking up with a trans guy. There’s a lot more people who want to do a secret, behind closed doors thing, because they’re publicly embarrassed by it. There’s such a culture of disgust for the vagina in those circles, and I’ve definitely found some gay men feeling like it takes away their gay card to be sleeping with someone who has my kind of junk.”

Years of navigating the casual sex scenes in various cities (he’s lived in Perth, Tasmania and San Francisco, along with his extensive touring schedule) have given him a good insight on the best and worst ways to hook up. He shies from bathhouses and sex clubs, preferring to lay his junk on the table before he starts taking bids. He’s experimented with apps and websites. But his hottest hook ups come from the place most people turn for used furniture and scalped concert tickets.

“With apps it’s much harder to pinpoint if someone is open to being with a trans guy,” he says. “You can scroll through hundreds if not thousands of profiles and not know who to go for. Beyond that, there’s just a lot of transphobia coming through. But I remember being totally flabbergasted the first time I got on Craigslist and saw all these people posting specifically that they wanted to be with a trans man.”

He’s found no shortage of lovers, though dating-while-trans often means adopting the role of educator while cultivating an ample sense of humour. There’s a stark divide between how trans women and men are portrayed in the media — the former often being objects of ridicule, the latter more or less invisible. No matter how clear he is in his pre-hook-up communication, guys still show up unsure of exactly what they’re getting into.

“I’m always going to do a particular array of things to try to avoid awkward, painful situations,” Drake says. “But sometimes you still get someone turning up saying, ‘Um, so you got your dick chopped off, right?’ There’s also times when guys get really turned on but in a kind of scientific way, like, ‘Wow, you have a vagina. That’s so interesting.’”

So if performance attendees come hoping to score a little nookie, does he have any tips on how to sweep him off his feet?

“I’m actually a bit shy after a show so it’s not the best place to try to pick me up,” he says with a laugh. “But I know for sure there have been few hook ups with other people that have happened after performances. We should actually do a survey of our audience to see what are stats are on that.”