Episode 1
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
Episode 2
Josh's students compete for an invite to the exclusive and elusive dating app, Orion. Ruby has near success at the dog park, and a full meltdown in class. Guest Starring: Jillian Vogel, Dave Futernick, Chloe Carabasi
Episode 3
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
Episode 4
Ruby desperately tries to extend his date with Martha. Martha imparts some harsh wisdom. Guest Starring: Nikki Taguilas-Pierce
Episode 5
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
Episode 6
Ruby prepares his home for what he's hoping will be the event of a lifetime. Josh tries to make peace with Ruby. Guest Starring: Dana Marcolina, Jon Gabrus
Episode 7
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
Episode 8
Ruby hires an exciting cleaning service, but things don't go as he fantasized. Josh tries to keep Ruby from disrupting the camaraderie during a late night session. Guest Starring: Veronica Osario, Colton Dunn, Chris Redd, Jake Nordwind.
Episode 9
Ruby flexes his comedy muscles on a date. Josh then helps Ruby break down exactly what went wrong. Guest Starring: Katie Marovitch, Alexander Koehne
Episode 10
Ruby finally hears back from Orion. The decision changes both Ruby and Josh's his life forever. Cast: Kristen Brancaccio, Hayley Marie Norman.
