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Let’s talk about sex — the awkward kind

From left: Ginny Leise, Jamie Leelo, Natalie Wall, Emmy Harrington, Carly Ann Philbin, and Meghan O’Malley.
From left: Ginny Leise, Jamie Leelo, Natalie Wall, Emmy Harrington, Carly Ann Philbin, and Meghan O’Malley. Meredith Truax

Awkward moments and shameful secrets have long been a part of the comedic landscape. Those elements have been honed to a fine point in live shows like “Mortified” and on television in “The Office” and “Curb Your Enthusiasm.” And there is a plethora of themed showcases for confessional comedy, but “Awkward Sex and the City,” which plays Laugh Boston on Thursday, has its own twist.

The show’s founder, Natalie Wall, found in her college years that women were reluctant to talk realistically about sex and how awkward the whole proposition can be. “We’re at our most vulnerable with people, and weird things happen and, like, why is this not being talked about?” she says. “It’s [expletive] hilarious.”


A year and a half ago, Wall tapped a group of fellow comedians and organized a show at People’s Improv Theater in New York City that featured them telling stories about true-life sexual experiences. That resulted in regular shows and tours with the frequently graphic, sometimes sweet “Awkward Sex and the City.” As the title suggests, the content is intimate and cringe-worthy. But the women of “Awkward” wear their awkwardness with pride.

“I think shame is a useless emotion that I waste a lot of time feeling,” says comic Ginny Leise, a member of the touring group. “So I think the point of the show is that you let other people feel less ashamed of their own lives and their own screw-ups and failed sexual encounters.”

Wall is especially happy with that aspect of the show. “No one ever plays the victim card. Like, ‘Oh, that’s so sad this happened to me,’ ” she says. “All the girls, and the people who do the shows, are like, no, this is [expletive] hilarious. These are all my choices.”

The tone is joyful, a celebration of the oddities of sex and pursuing sex. To the six women who make up the rotating tour company, it’s like a conversation friends might have privately. “It feels like an adult sleepover,” says Carly Ann Philbin, another core member of the group. “Everyone’s drinking. We’re talking about boys. There aren’t any tears. We’re just talking about our life experiences, and that is definitely the feel of the show.”


Those life experiences vary wildly. Leise has a story about an encounter with a bear while she was having sex in the wilderness. Wall talks about a tryst she regretted immediately, leaving a man to shout her name mournfully when a friend rescued her from his apartment. Philbin, who thinks of herself as the more romantic, emotional member of the group, recounts one strange way she was hit on. “One time somebody came onto my fire escape and left a note on my window,” she says. “It was really creepy, but I kind of flip it, saying, well, maybe it’s not the worst thing to have a hook-up that lives in your building.”

At a time when sex is used casually to sell everything from beer to Web services, and TV is racier than ever, it is counterintuitive to think the topic is underrepresented in public discourse. “I think the biggest difference [with the show] is, this is sex through a female lens,” says Leise. “I think you see a lot of sex everywhere, but it’s through a male lens. A lot changes when you give control of the narrative to a different point of view.”


Wall has seen how the show helps members of the audience open up a bit more. “They don’t have this outlet to talk about it as much,” she says, “and then the show kind of gives them this very safe place to watch and relate. I’m always approached after shows with people’s personal awkward sex stories. Everybody has one. It’s a very universal topic.”

Proof lies in how much the show has grown in popularity since the first performance in August 2013. Wall puts together frequent tours, and the Laugh Boston show will be the fourth time “Awkward” has hit Boston, at three different clubs. And there are plans to bring the show back to Oberon in July. In New York City, the show includes members of the core touring group and male comedian guests. It currently runs monthly at the Museum of Sex, but Wall says she will soon move to a weekly schedule. “It’s been crazy to see it grow,” she says. “It’s been fun.”

To Leise, the best comedy is honest, and she believes audiences are reacting to the vulnerability of women talking about their real lives and having fun. And she sees “Awkward” as part of a trend toward powerful female comics in New York.

“There’s just so many young women doing great things that are just so fully accepting of who they are and not into self-deprecation in a way maybe other generations have,” she says. “I’m speaking in broad strokes. But I just feel there’s a really empowered comedic female voice coming out of New York right now, and our show really captures that.”


Nick A. Zaino III can be reached at nick@nickzaino.com.