Ruby Jade has to compete with a charming bartender on a date. Josh tries to keep control of his clas...

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

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

Ruby desperately tries to extend his date with Martha. Martha imparts some harsh wisdom. Guest Starr...

Josh runs into Ruby and gives him the surprise of his life. Unraveling, Ruby spirals into an impromp...

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

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

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

Ruby flexes his comedy muscles on a date. Josh then helps Ruby break down exactly what went wrong. G...

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

Ruby Jade is back and wants to return to Josh's class, if not as a student, then as a teacher's assi...

Ruby learns that the dating climate has changed in the last few years and uses his newfound knowledg...

Ivan and his groomsmen try on their tuxedos for the big day. Ruby plays a nasty prank on Ivan.

After a strange hypnotherapy session, Ruby spends 'game night' trying to cozy himself up to his date...

After a strange hypnotherapy session, Ruby spends 'game night' trying to cozy himself up to his date...

Ruby attempts to impress his date with his intellect as they try to navigate an escape room.

Ivan's bachelor party is in full swing when Ruby considers this his time to shine.

Ruby and Raj square off in a series of escalating feats of stupidity.

Ruby has a huge crush on somebody at Ivan's wedding but doesn't know how to let her know.

Ruby makes the biggest decision of his life.