|"When Will Josh See How Cool I Am?"|
|Season 2, Episode 2|
|Premiere date:||October 28, 2016|
|Written by:||Rene Gube|
|Directed by:||Jay Chandrasekhar|
|Previous Episode:||"Where Is Josh's Friend?"|
|Next Episode:||"All Signs Point to Josh...Or Is It Josh's Friend?"|
|Featured Musical Numbers|
|“||Dude, you're getting sober, you're not turning into a robot. It's okay to have feelings.||”|
Rebecca (Rachel Bloom) desperately wants Josh (Vincent Rodriguez III) to think she's cool so she tries to impress him with her sporty skills. Meanwhile, Greg (Santino Fontana) is navigating his way through his new path, and is sorely tested by someone close to him.
|Maybe This Dream||Paula Proctor with Tim and Jim||Paula sings the song after she tells Rebecca she's applying to law school|
|Greg's Drinking Song||Greg Serrano and chorus||Greg sings the song in the bar after he tells his friends he's an alcoholic|
|I Could If I Wanted To (reprise)||Greg Serrano||Greg sings the song as he punches the wall|
|Ping Pong Girl||Josh Chan||Josh and his band perform the song after Rebecca practices playing ping pong with Xiao Wong|
- Rachel Bloom as Rebecca Bunch
- Vincent Rodriguez III as Josh Chan
- Santino Fontana as Greg Serrano
- Donna Lynne Champlin as Paula Proctor
- Pete Gardner as Darryl Whitefeather
- Vella Lovell as Heather Davis
- Rene Gube as Father Brah
- David Hull as White Josh
- Erick Lopez as Hector
- Jayden Lund as Guardrail
- Michael McMillian as Tim
- Johnny Ray Meeks as Kevin
- Steve Monroe as Scott Proctor
- Burl Moseley as Jim
- Albert Tsai as Xiao Wong
- Tom Beyer as Hubcap
- Hayden Maringer as Guitar Player
- Cory Tramontelli as Bass Player
- Cameron Tyler as Drummer
Josh: That's what I love about you.
Rebecca: You love me?
Josh: Love ABOUT you.
Darryl: I don't know but I'll find out. I'm her best friend. Everyone knows that, right?
Tim: Everyone knows you say it.
Josh: I was the one with the fake ID in high school. At every party I would dare you to drink the whole bottle because I thought it was funny or something. God, I don't know if I can live with myself anymore.
White Josh: Weirdly, this isn't about you.