"When Will Josh See How Cool I Am?"
Season 2, Episode 2
Episode Information
Premiere date: October 28, 2016
Viewers: 0.45
Written by: Rene Gube
Directed by: Jay Chandrasekhar
Episode Chronology
Previous Episode: "Where Is Josh's Friend?"
Next Episode: "All Signs Point to Josh...Or Is It Josh's Friend?"
Featured Musical Numbers
Related Pages
Dude, you're getting sober, you're not turning into a robot. It's okay to have feelings.
When Will Josh See How Cool I Am? is the second episode of Season Two of The CW's Crazy Ex-Girlfriend. It was written by Rene Gube and directed by Jay Chandrasekhar. It is the twentieth episode of the season overall and premiered on October 28, 2016. "When Will Josh See How Cool I Am?" attracted 0.45 million views.


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.


Song Sung By Happened
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




Memorable Quotes

Josh: That's what I love about you.

Rebecca: You love me?

Josh: Love ABOUT you.

White Josh: So Greg knows that you and Rebecca are together? Oh no – Greg is probably freaking out.

Tim: What's with Paula Proctor?

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.