Season 2

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.