Illustration by Aditi Singh

With a microphone in her hand and a beam of light shining on her, Natalie Wall tells a crowd the story of how she lost her virginity. Minutes later, Karolena Theresa takes the stage, and with a giggle, shares with the audience that she once peed on a guy during sex. 

This is the comedy show “Awkward Sex and the City.” The show has been running for over 10 years now, and over that time, has evolved into a podcast, regular shows in New York City, and a nationwide tour with three other rotating comedians.

F Newsmagazine had the privilege of interviewing Wall and Theresa on their experience as female comedians who talk about sex. Here is what we learned: 

How did “Awkward Sex and the City” begin?

It all started during the slut-shaming culture of the early 2000s. Natalie Wall, the creator of “Awkward Sex and the City,” describes herself as a “super late bloomer when it came to sex.” The topic of sex was so taboo back then that it felt like no one dared share information about it — much less laugh at it. Wall sought to create a safe space for people who, like her, wanted to talk about this mysterious topic, and, thus, “Awkward Sex and the City” was born. 

Theresa, meanwhile, went to a performing art high school in New York and was classically trained in theater. She didn’t know she was a comedian until she played Nick Bottom in “A Midsummer Night’s Dream.” She started her career with a few sketches in college, trained in “improv” at Second City, and then slowly transitioned into stand-up. Now, she’s a consistent part of “Awkward Sex and the City,” performing with them regularly. She’s always had a natural inclination to talk about sex and its subsequent themes of femininity and family. 

Why talk about sex? 

“Sex is such a universal topic,” Wall said during the interview. It is a topic that most people, of most ages, can relate to, and its appeal is evident in the show’s audience. The two women said they usually have a wide range of spectators, from ages 18 to 70, in attendance. 

According to them, it’s easy to connect with people when talking about sex. It’s a topic that people are curious about, fantasize about, and have fun talking about. Most people have an opinion on sex — or a story to tell — so it’s universal. Nevertheless, despite society’s new openness towards sex, they can tell that some people still tense up at the mention of certain topics such as polyamory. 

But connecting with other people, and entertaining them, is only a fraction of what Wall and Theresa are doing. The biggest reason these women want to talk about sex is to create awareness and representation.

 “This widespread lack of information about sex is a dangerous trend,” Wall said, going on to say, for example, only 18 states in the United States require sex education to be medically accurate and include information about birth control.

“It is a privilege that I was able to open my perspective,” continued Wall. She began the show as a straight girl, and talking about sex on stage opened her eyes to a lot of information about queerness and sexuality that she did not know about.

“There are a lot of different types of horny and sexual people in the world. It’s okay not to know and to do research on sex,” said Theresa.  

At this comment, Wall laughed. She said the television show “Sex and the City” inspires her comedy, as every woman in the show is supposed to be a stereotype of a different type of woman. Nevertheless, she tries to take it a step further in her comedy and explore how people have multitudes — how we can all simultaneously be Carrie, Samantha, Miranda, and Charlotte.   

“People want different types of sex on different days,” Wall said.  

Back to the topic of representation, Theresa said she was proud to talk about her personal experience as a way to shine light on her intersectional identity. Her family comes from Trinidad, Guatemala, and New York. When she talks about her husband, a Muslim man who grew up in a traditional family, she is also creating representation for him. 

Representation also touches on the personal aspects of sex comedy and how much of a comedian’s story on stage is true versus invented. 

 “Where do you exaggerate? Where do you omit? Stories sometimes have to be changed to be funnier. It’s important to be as truthful as possible within the stories you tell. It’s important to be honest because it connects to representation and real empowerment. You should never punch down at the other person: laugh at a situation, not a person. Stay truthful but respectful.” Wall said, weighing in on her thoughts about how to tell a good story on stage. 

Theresa shared similar thoughts, saying she can only represent herself, but that her story needs to be heard.
“Being truthful keeps you grounded and funnier. It allows other people to interpret what you said…and learn from it…and make it theirs. The relatability is the funniest part,” said Theresa. 

Are there any downsides to talking about sex in comedy?

Wall and Theresa said that so far no one has ever been heckled at the show, despite it being a major safety concern. The reason for their success is transparency: the people who go to “Awkward Sex and the City” know that the show is going to be about sex. One of the limitations of the topic is that it can’t be sprung on people without their consent, so the effect of advertising a sex-focused comedy show is a compact, but interested, self-selected audience.

In their personal lives, both Wall and Theresa have partners who are supportive of their sex comedy. Wall said that only once did her partner say they did not want a personal joke told, and only once did Theresa’s husband not want to be in the room during a bit.

What is the future of sex in comedy? 

Theresa thinks comedy is ever-changing. It was already at a tipping point when she started her career in the early 2000s. Back then, female comedians couldn’t present too feminine because they had to fit in with the guys to prove they were funny. It was the collective effort of the queer community and of people of color who made space for unique, authentic, and alternate forms of comedy through creating their own shows. 

“[These communities] were funny while dressing however they wanted, and it forced the comedy world to change,” Theresa said. “People will judge you based on appearances, but after you go on stage and prove you’re funny, they can’t judge anymore.” Marginalized communities still have to fight to be recognized in comedy, but Theresa believes there is a bright future ahead. 

Wall believes sex in comedy has potential because there is only space to grow. She says people are now more open about the topic than ever before. Talk about sex is booming because of its newfound permissibility, and that will lead to a new generation of sex comedians (with a, hopefully, greater understanding of inclusivity, consent, and the dangers of misogyny). 

What is your advice for sex comedians? 

“The more you’re able to embody yourself, the bigger the depth you have to convey a story and connect with the audience. People are craving authenticity. There are days in which you don’t know who you are, and that is okay. It takes time, and it is a journey, and your style and persona will change, but the best persona is a heightened version of who you are,” Natalie Wall said with a smile. 

Karolena Theresa nodded along, adding that “If someone wants to do comedy, do not forget to be kind and empathic with others. Do not copy others. Be here to party and have a good time — consume the comedy that tickles you. And have sex! Have a lot of sex, and don’t be concerned that there’s a right number of how many times you’re doing it. Sex is like comedy: if you want to do comedy, do it. It will open up your world. But do it when you’re ready. The same with sex. Trust your gut.”