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- Ruby (Amir) is in deep deep desperation for a girlfriend. He is seen on a date and it can be seen why he still doesn't have a girlfriend.
- Ruby attempts to get an invite to a "super exclusive, high end dating app" called Orion through an opportunity provided by Josh to his class. Ruby desperately tries to get the invite that could potentially change the "dating game".
- 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.
- Ruby desperately tries to extend his date with Martha. Martha imparts some harsh wisdom.
- 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.
- Ruby prepares his home for what he's hoping will be the event of a lifetime. Josh tries to make peace with Ruby.
- Ruby attempts to get in shape by hiring a personal trainer. Back in class he practices pickup lines on Ivan.
- 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.
- Ruby flexes his comedy muscles on a date. Josh then helps Ruby break down exactly what went wrong.
- Ruby finally hears back from Orion. The decision changes both Ruby and Josh's his life forever.
- 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.