Josh is having a difficult time moving on after his girlfriend Maggie dumps him. His best friend Mike tries to help him get over her by encouraging him to find a new girlfriend.
Josh struggles to start a text conversation with a new potential girlfriend named Laura, so he seeks out the advice of his friends.
Josh and Mike head for a night out at the club with hopes of finding a hook-up, but Josh's insecurity gets the better of him when he realises he doesn't know how to pick up women.
Josh's family sets him up on a blind date with Maude and pushes him to settle down with her. Uninterested, Josh goes to extreme measures to avoid Maude.
A beautiful woman takes interest in Josh, but his insecurity leads to jealousy of other men talking to her, getting in the way of the relationship.
Josh finds a new girlfriend named Kayla and their relationship is going well until Maggie makes her way back into Josh's life.
Jay Baruchel
Josh Greenberg
Eric Andre
Mike Bunk
Britt Lower
Liz Greenberg
Maya Erskine
Maggie
Robin Duke
Patti