Maddy Smith (MTV's Wild N' Out, New York Comedy Club) chats about spinning, corporate burn out, and how Wild n' Out taught her she was bad at dancing.

Get a taste of our live shows featuring Michelle Drozdick on solo improv, Ricky Downes III on flirting with monkeys, and Aimee Rose Ranger on weird gifts.

Christiana Jackson (the Harlem Comedy Festival) lets us in on the awkward, irritating, and racist side of real estate.

Gabby Bryan (Unabashed podcast, the Comedy Cellar) is an open book in life...and on this podcast! We talk about getting confident, nude scenes, partying at twelve, dental issues, and much more.

Jay Jurden (the New Yorker, Stand up NBC, MTV News) talks about being a theatre kid, working as a personal trainer, and his comedy journey.

Derek Humphrey talks about growing up as a big kid, joining the navy, and getting out of his small town.

Aarushi Agni (frontwoman for Tin Can Diamonds, comedian, and writer) shares what it was like moving to NYC, her creative process, and realizing awkward moments happened well after the fact.

Comedian and Model Chris Moore uses pranks to combat social awkwardness, with results ranging from regrettable to hilarious. Plus lots of poop-talk. Instagram: chris.moore.poops.2

Sheree shares the ups and downs of dog walking, comedy, and; would it really be an episode of How to be Less Awkard if we didn’t get into masturbation?

Jacob Williams (The Late Show with Stephen Colbert, Wild N’ Out, America's Got Talent) talks about getting awkward after first grade, why you shouldn't buy your ex gifts, and how Ace Ventura played a part in his sexual awakening.