Awkward Sex... and the City

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. - The Boston Globe

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."

What’s your most recent awkward sex story?

I'm in a new relationship and the first — we've been together for four months or something — but the first time we had sex, I got explosive diarrhea right after it.

Oh, God.

It's hilarious and he was great about it. And I was like, "I know you're a good guy because of this." It was at his place. It was terrible. I'm not far enough from the story yet to do the whole story in a performance. I've done bits on it, but you do have to — you'll feel it. You'll kind of be like, "I'm ready."

Thanks to comedians like Amy Schumer and the Broad City girls, it seems like women talking honestly — and raunchily — about sex is much more mainstream than it was two years ago when you first started. Is that true? Was there already a space for "Awkward Sex" or was it more challenging to get your show going because there were fewer women doing shows like it?

I don't think it was mainstream yet. Like, Amy Schumer was getting big but she wasn't the goddess that she is now, Broad City wasn't around — Sarah Silverman was talking about sex, maybe — but there was definitely a space for it. It has never been hard to book the show, and it's always been a good audience — the audience is always so on your side because they know what they're getting into. Like, they know they are going to hear stories about awkward sex. Nothing is being hidden from them.

In your experience, what is the general reception when female comedians speak so openly about their sex lives?

So far, I've definitely been lucky. But, there are still some experiences that piss me off, like once while I was on tour we were in the bar and we were talking to some people that came. And I was talking to a dude and his girlfriend. And we were talking about awkward sex stories and he slapped my ass. I was like, "What did you just do?" And he was like, "You just talked about sex. I can do that."

I think it was Amy Schumer who said ... You know, she's been labeled a sex comic, but a guy can go on and talk about his dick for an hour and people call him a "thinker." Sexism is so ingrained in our society that it's going to be a really long fight. Because there is always going to be these moments: two steps forward, three steps back.

What will change it?

This year, I co-founded and co-produced Bad Assery, the women in comedy conference. It was a lot of amazing women doing their thing and kicking ass. And I think the louder we get, the more and more we put up a fight, the more we start highlighting the people who are being assholes, the more it will change. We need to really fight and come together. I think it was Sara Schaefer a week or two ago on Twitter that was like, "Girls, the only other lady at the open mic isn't your enemy. She's your best friend." Like, we have to stop trying to compete against each other, and try to work together. The whole Shine Theory, have you heard of that? I think that's a main factor in being able to fight this. The more that we fight these stereotypes — the ones men use to put women down: They're catty, they're emotional, blah blah blah. The more that we're like, "No, that's not true and here's some examples." The more we do that, the more they’ll have to shut up a little bit.

Your show has raunchy sex stories, but you also discuss that the underlying message is one of sex positivity — do you think that your show helps women feel more sexually liberated or is it changing the way women's sexuality is perceived?

I really hope so. And I think it is. After every show, people will come up and they want to tell me their awkward sex story, because people never want to talk about it. They feel like it's not a safe environment, and now I've provided them with that environment, and now they can go talk more. It's something I noticed in college: All the girls wouldn't talk about masturbating, or they're like, "I don't masturbate. That's not a thing I need." And I was like, "I do it all the time." And then two weeks later everyone was like, "I have a vibrator. This is the porn I like." They just need that one person to be like, "Well, I do it and it's great."

I want people to have knowledge and I want them to feel open and comfortable. I think these shows are helping inspire sex positivity for everyone. And I think they're just helping people enjoy sex. I think my main thing is I want everyone to really enjoy it. And the one way to do that is give zero fucks what you look like. Give zero fucks what you're doing. And just get as vulnerable as you can. And really just fuck. And that's when the orgasms come. - New York Magazine

These days, comedy is all about being honest. Or it’s about not being afraid to make a fool of yourself in front of hundreds of people. And if you’re into both, you’re in luck, because these two shows are the whole package.

Awkward Sex…and the City

In an era of Lena Dunham and Amy Schumer, we’ve traded in the old Hollywood vision of sex as glamorous and mysterious for something much more raw, personal, and often unpleasant. That’s what “Awkward Sex…and the City” is all about.

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In 2010, Natalie Wall had just graduated college. As a creative outlet, she began to blog about her intimate experiences as a Macy’s retail worker with adult braces. Five years later, this blog has turned into a full-blown, all-female show.

Hosted and produced by Wall, “Awkward Sex…and the City” stars Meghan O’Malley (The PIT), Carly Ann Filbin (Upright Citizens Brigade), Jamie Leelo (Brunch Night! with Jamie Leelo), Emmy Harrington (HBO, Reno!911), and Ginny Liese and SJ Son (both of The Shame Game). Each woman takes the stage for 15 minutes to spill her most uncomfortable, hilarious sex story.

But it’s not all just about the laughs. The show intends to open up a dialogue about the most private part of our lives in order to diffuse the stigma that surrounds women’s sex lives and help people feel a little more comfortable with their sexuality.

These ladies have seen it all: a bear encounter while going at it in the Alaskan wilderness, a love note from a creepy neighbor taped to the windowsill, a desperate attempt at buying Plan B on an Easter Sunday in the Deep South. And tonight at the Oberon, the awkward tales just keep coming.

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As Wall puts it, “You can’t make this shit up.”

August 6, 8:30 p.m., $15-$20, OBERON, 2 Arrow Street, Cambridge, 617-496-8004, americanrepertorytheater.org.

Mortified

Our prepubescent years were defined by aggressive acne, middle-parted ‘dos, and alarmingly low self-esteem. And while most of us try to repress memories of those glory days, “Mortified” chooses to revel in it instead.

Considered a “cultural phenomenon” by NewsWeek, the show has grassroots chapters all across America and even has its own podcast. It features a cast of adult strangers sharing their most private, most embarrassing adolescent artifacts in front of an audience of total strangers. Think diaries, love poems, song lyrics…the whole shebang.

You’ll be cringing the entire time. But then you’ll go home and open up your old childhood journal, and look back at that time in a whole new way (after you die a little inside). Maybe you’ll even choose to participate in the next show. Because nothing brings people together like “sharing the shame.”

August 6, 7:30 p.m., $15-$18, Coolidge Corner Theatre, 290 Harvard St., Brookline, 617-734-2501, coolidge.org; August 7, 7:30 p.m., $15, OBERON, 2 Arrow St., Cambridge, 617-496-8004, americanrepertorytheater.org. - Boston Magazine