At age 14, comedian Natalie Wall wasn’t having sex, but she could absolutely provide you with any information you might need to know about anatomical instruction or details about STDs.

“I came from a very open family. My mom would say things like: ‘You need to experiment. Get your fucking O. You need to have sex before marriage. You need to know.’ None of my friends’ parents were talking to them like that, so I became the person who knew stuff even though I hadn’t done anything. My friends were losing their virginity at like 14 and 15 and I was like, ‘I’m not, but I can answer all your questions about STDs and I can tell you what your clit is,’” she told us recently.

As a college student, Wall recalls leading discussions about vibrators and masturbation with her dorm mates, encouraging them to discuss their sex lives openly — no matter how good, bad, weird, liquid-y, smelly, or horrendously embarrassing the encounter was. “A lot of times we’re told not to talk about, appreciate, dissect, or feel comfortable with having weird sex. I like to make people feel better about it.” Five years after graduating, Wall is still making people talk about it, just on a much larger scale with her monthly comedy show, “Awkward Sex … and the City.”

The show, a spinoff of her blog by the same name, asks comedians to recall those squirmy sexual encounters they’ve locked in some inner shame box, and share them with an audience. It seems like torture, but it’s more like wine-soaked catharsis for everyone involved. On the eve of the second anniversary of her show, we spoke with Wall about finding comedy in the cringe-worthy, how to combat sexism, and the one awkward sex story she’s not quite ready to tell.

What makes a really good awkward sex story, as opposed to one that just makes everyone cringe uncontrollably?
Every story that I’ve heard so far, and the show’s coming up on its second anniversary, has been totally unique, it’s never been similar to any other story I’ve heard. Ever. I guess the best awkward sex stories are always — they’re very self-deprecating. They’re the most honest and the most vulnerable. And it’s always really good to have something random happen. Like, one of the stories from the show tonight: They’re up in Alaska and a bear punches through a glass window while they’re doing it. That’s never going to happen to anyone else except maybe five other people, and it’s just so random and crazy that you’re like, “That is amazing.”

Keep Reading