The Worst Episodes of Lonely and Horny

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

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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

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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

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

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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

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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

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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

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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.

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

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

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

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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.

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

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

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

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

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

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

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

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Ruby makes the biggest decision of his life.

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