Let’s Talk About (Awkward) Sex

An Oakland-based podcast makes awkward sex stories funny.

Sitting around with friends and telling awkward sex stories has always been Carey Callahan’s idea of a good time. But the comedian and Bay Area transplant didn’t think to make a career out of this hobby until a friend suggested that he and his sister, Bridget Callahan, who’s also a comedian, start a podcast. Centering the show on weird sexual encounters seemed like a natural choice.

“A lot of media about sex is public health warnings or the best ways to have sex,” said Carey. “We wanted to talk about stuff that doesn’t fit into those things. It’s not about how to have sex, it’s about how people have had sex, and not even the best sex.”

Carey and his sister started the podcast, The Awkward Sex Show, in Cleveland, Ohio in July 2012 and have since recorded 32 episodes. Described as “30 percent comedy, 30 percent the kind of therapy you get when you go to the bar with your best friend, and 40 percent telling embarrassing stories in front of strangers,” the show has featured stories about topics such as the parental sex talk and a former dominatrix’s experience dressing men up as women. The podcast did well in Cleveland, but after several months of recording there, Carey felt as though he and Bridget had reached the limit of the types of sex stories that people were willing to share. He decided he wanted to move to a place where people were more open. “Oakland has a rep,” he said. “That’s what people in Ohio know about the Bay Area, … that people talk about sex a lot here.”

After moving to the East Bay without his sister, Carey began to search for a new partner. He found her after one of his stand-up shows in which he discussed an awkward threesome: Fellow comedian Jennifer Dronsky came up to him and said, “I have to tell you all about my threesome.” “My willingness to tell him utterly terrible stories about myself sexually made him think, ‘Oh yeah, this person should definitely be on the show,” said Dronsky.

This Sunday, Dronsky and Callahan will host their third live recording in the Bay Area of The Awkward Sex Show at The Stork Club (2330 Telegraph Ave., Oakland) on Sunday, September 29. Each podcast has a theme — past ones have included pregnancy, Craigslist, and bad advice — and this week’s is competition. Callahan always chooses a couple of storytellers in advance, but also allows audience members to participate — often, he said, those stories are the best. “Someone always has a story,” said Callahan. “They just need to listen to the show, get their brain working, and maybe drink a little bit.”

The Awkward Sex Show is gaining a following: It has about 650 subscribers, was downloaded 12,000 times last month, and drew about 50 people to its first Oakland show. Dronsky and Callahan’s goal is to do a live event every other Sunday throughout the fall and to make it a weekly event next year. Who would be their dream guest? Callahan had to think about it. “Willie Nelson,” he finally wrote back in an email. “I’m a huge fan and you KNOW Willie would have the best stories.”

6 p.m., $5. AwkwardSexShow.com


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