Lonely and Horny

Ruby Jade has to compete with a charming bartender on a date. Josh tries to keep control of his classroom as people start to gang up on Ruby. Ruby makes a solemn promise. Guest Starring: Milana Vayntrub, Ben Rodgers, Chris Redd

Thanks to a new dating app, Ruby has the most interesting sex of his life. Josh allows Ruby to regale the class with his exploits. Guest Starring: Punam Patel, George Basil, Ariana Madix

Josh runs into Ruby and gives him the surprise of his life. Unraveling, Ruby spirals into an impromptu date with a driver who picks him up. Guest Starring: Kelly Hudson, Hayley Marie Norman, Angela Trimbur, and Mason Cooper

Ruby attempts to get in shape by hiring a personal trainer. Back in class he practices pickup lines on Ivan. Guest Starring: Alex Marshall Brown, Billy Scafuri, Jake Nordwind

Ruby flexes his comedy muscles on a date. Josh then helps Ruby break down exactly what went wrong. Guest Starring: Katie Marovitch, Alexander Koehne