Aired: 11/5/2018
Ruby Jade is back and wants to return to Josh's class, if not as a student, then as a teacher's assistant.
Aired: 11/12/2018
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.
Aired: 11/19/2018
Ivan and his groomsmen try on their tuxedos for the big day. Ruby plays a nasty prank on Ivan.
Aired: 11/26/2018
After a strange hypnotherapy session, Ruby spends 'game night' trying to cozy himself up to his date's friends.
Aired: 12/3/2018
Aired: 12/10/2018
Ruby attempts to impress his date with his intellect as they try to navigate an escape room.
Aired: 12/17/2018
Ivan's bachelor party is in full swing when Ruby considers this his time to shine.
Aired: 1/7/2019
Ruby and Raj square off in a series of escalating feats of stupidity.
Aired: 1/14/2019
Ruby has a huge crush on somebody at Ivan's wedding but doesn't know how to let her know.
Aired: 1/21/2019
Ruby makes the biggest decision of his life.