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

Ruby learns that the dating climate has changed in the last few years and uses his newfound knowledge on an artisan salsa maker named Sarah.

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's friends.

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

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.

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.

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 desperately tries to extend his date with Martha. Martha imparts some harsh wisdom. Guest Starring: Nikki Taguilas-Pierce

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

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

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

Ruby finally hears back from Orion. The decision changes both Ruby and Josh's his life forever. Cast: Kristen Brancaccio, Hayley Marie Norman.

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

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