Awkward Sex and the City


“It is a storytelling ode to the universal experience of sex as awkward, weird, silly, hot, and awesome (sometimes all at once, sometimes distinctly not).” – BUST


Awkward Sex and the City consists of 5 comedians, Natalie Wall, Bobby Hankinson, Jen Keefe, Karolena Theresa, and Anita Flores.

Natalie Wall is the creator/producer/headliner of "Awkward Sex... and the City," which showcases comedians with hilarious awkward sexual tales. She writes for Redbook Magazine and, specifically about sex and relationships. In 2015 she co-founded Bad Assery: The Women and Comedy Conference. When Natalie is not working on "Awkward Sex" she can be seen performing stand-up all around New York City or hosting her brand new show, Sex! With Your Mom!, the adult sex-ed game show. She has trained with The People’s Improv Theater and James Madison University.  When Natalie isn’t performing stand-up she’s watching a shit ton of Gilmore Girls (no seriously, it’s a problem) and not wearing pants.

Bobby Hankinson is a Brooklyn-based comedian, storyteller, and host of Kweendom. He is a columnist for leading LGBT website and his writing has appeared in the Boston Globe, the Houston Chronicle, and Brokelyn. Bobby has studied improv at the Upright Citizens Brigade Theater. You can catch him performing throughout New York City or sitting at home, mainlining episodes of Ink Master and pinning pictures of Channing Tatum to his Pinterest.

Jen Keefe is a comedian based in New York and loves the Boston Bruins. She has performed on NPR’s “The Moth StorySLAM”, as well as at popular venues such as Littlefield, Bowery Poetry Club, Creek in the Cave, and The Bell House, in the cafetoriums of various high schools, and at her dad’s retirement party. Named a “2016 Comedian to Look Out For” by Mogul, she produces Dickbusters, a monthly female-centric variety show, and a web series she wrote and is starring in goes into production this April. Jen is an ordained wedding officiant and would love to do your wedding… just ask!

Karolena Theresa is a stand-up comedian, actress, writer, and singer from Queens, New York.  Karolena has studied at The People’s Improv Theater, Upright Citizens Brigade, and Second City, and has received diversity scholarships from both UCB and Second City. Karolena also hosts two monthly shows in New York City: The Black Out, a show that features comedians from the POC and the LGBTQ Community, and Big Mouths, a show that features women and LGBTQ comedians.  She has been featured on Refinery29 and in variety of media platforms representing body positivity. You can catch her performing stand-up all over New York – well, mostly Brooklyn.

Anita Flores has written for Above Average, Nerve, Paste Magazine, Portable TV, and Laughspin. She's performed at The Moth, How I Learned, Tom Shillue's Funny Story, and many other shows around New York City. She has a web series called Questionable Drawings where she asks comedians weird, often inappropriate questions and animates their responses. Watch it on the internet and follow her on Twitter at @anitajewtina for important updates on pizza and Kelsey Grammar's career.




Five comedians divulge their most intimate and awkward sexual and dating experiences packed into a tight 90-minute show for your viewing pleasure. Kinky, we know. Holding back no punches, this gang breaks barriers about sex, relationships, and dating taboos while making you laugh hysterically. The show pairs sexual inclusion with humor swimmingly and sheds light on the awkward universal experience we all know and love (for the most part). “Awkward Sex… and the City” has sold out multiple venues and received glowing reviews from The Boston Globe, Brightest Young Things, BUST Magazine and more. If you ever felt weird about sex, sexting, flirting, what have you, never fret, Natalie Wall, Bobby Hankinson, Anita Flores, Karolena Theresa, and Jen Keefe will make you way better about yourself and all your life choices.