Awkward Sex is exactly what it sounds like: comedians reliving intimate tales about their sex life and breaking barriers about sex and dating. Hosted by Natalie Wall, the show pairs sexual inclusion with humor and sheds light on the awkward universal experience we all know and love. Awkward Sex is about taking taboo subjects and creating a safe space for people to feel seen and heard. From cocaine infused one night stands to IBS flare ups during cunnilingus, you and your friends will be hanging on to every word and excited to go out and have a sexual misadventure of your own. This month's line up includes: Emma Willmann Veronica Garza Tim Donnelly “Good sex is always good sex, but it takes a special person to turn bad sex into something amazing. And that’s where our New York comedian and podcaster Natalie Wall comes in.” -Philadelphia Gay News “The voyeur within will delight.” – Refinery29
SUBMIT UPDATES
Caveat Frequently Asked Questions FAQ
Caveat is at 21 A Clinton St, Manhattan, NY.
Constellations by Nick Payne (11/21/25-11/21/25)
Awkward Sex... and the City (11/13/25-11/13/25)
Fun in Moderation (11/8/25-11/8/25)
Rouge Salon Presents: Death Squared (11/2/25-11/2/25)
Catbaret! Purrsents...Meowloween (10/31/25-10/31/25)
Modern Whitney (10/25/25-10/25/25)
Jungle Restaurant (10/5/25-10/5/25)
Modern Whitney (9/27/25-9/27/25)
Mulatto Winnie the Pooh (9/15/25-9/15/25)
Fun in Moderation (8/22/25-8/22/25)
Constellations by Nick Payne (11/21/25-11/21/25)
Videos
 |
Broadway Magic Hour
Broadway Comedy Club (9/30 - 12/30) | |
 |
Strawberry Fields: Berry Christmas, Darling
Green Room 42 (12/18 - 12/18) HOLIDAY SHOW | |
 |
Down Once More
Teatro Latea (12/15 - 12/21) | |
 |
Lobby Hero
Manes Studio Theatre of Long Island (1/9 - 1/25)
PHOTOS
| |
|
THE NUTCRACKER
Ajkun Ballet Company at Ballet Arts Rudolf Nureyev Studio in the historic landmark The City Center (12/6 - 12/21) | |
|
The Outsiders
Proctors (5/19 - 5/24) | |
|
That 80s Improv Challenge: HOLIDAY & PUNK ROCK EDITION
TALE (12/18 - 12/18) | |
|
THE MUSEUM OF MODERN ART PRESENTS Artist’s Choice: Arthur Jafa–Less Is Morbid
The Museum of Modern Art (11/19 - 7/5) | |
|
The Brothers Size
Ujima Theater Company (2/27 - 3/8) | |
| VIEW SHOWS ADD A SHOW | ||
Get Off-Off-Broadway's #1 Theatre Newsletter
All the show news & discounts for Off-Off-Broadway & beyond.
