A young nurse is pressured to get married and have children. Her first and only boyfriend of ten years makes a hilariously inappropriate Internet video. A gay friend gets dumped for throwing his cat off the bed. Their best friend is a balding, 24-year-old virgin, and quickly becoming a 'creepy old man.' Sex is the theme in this ensemble piece, in which stigmas are challenged and a group of friends bare all.

Phyllis is going to visit her best friend in 2 days for her birthday. It occurs to Phyllis that a vibrator would be the best gift, because her friend has been sexually careless lately. She spends the next two nights in XXX shops, encountering awkward run-ins with her mother, friends, and giant dildos.

Having Fun Up There follows Mark, a 37 year old musician in crisis. Mark has long since given up on the idea of being successful with his music, but his relationships, job prospects, and self-esteem are strained by his desire to continue playing. Throughout the Fall, Mark tries to get a handle on his better-late-than-never adulthood, as his art continues to both destroy him and save him.