Ruby Jade has to compete with a charming bartender on a date. Josh tries to keep control of his classroom as people s...

Josh's students compete for an invite to the exclusive and elusive dating app, Orion. Ruby has near success at the do...

Thanks to a new dating app, Ruby has the most interesting sex of his life. Josh allows Ruby to regale the class with ...

Ruby desperately tries to extend his date with Martha. Martha imparts some harsh wisdom. Guest Starring: Nikki Taguil...

Josh runs into Ruby and gives him the surprise of his life. Unraveling, Ruby spirals into an impromptu date with a dr...

Ruby prepares his home for what he's hoping will be the event of a lifetime. Josh tries to make peace with Ruby. Gue...

Ruby attempts to get in shape by hiring a personal trainer. Back in class he practices pickup lines on Ivan. Guest St...

Ruby hires an exciting cleaning service, but things don't go as he fantasized. Josh tries to keep Ruby from disruptin...

Ruby flexes his comedy muscles on a date. Josh then helps Ruby break down exactly what went wrong. Guest Starring: Ka...

Ruby finally hears back from Orion. The decision changes both Ruby and Josh's his life forever. Cast: Kristen Brancac...