Tim thinks wearing a Cinderella dress during March Madness is good luck, so he refuses to take it off in hopes his alma mater will win. Also, Greg fantasizes about what to write in a birthday card for his boss, Tyler goes to prom and must withstand unsolicited advice from his parents and grandparents, and Jen sets Matt up on a blind date with her coworker, Dougie.
Quest roles:
Hunter King(Clementine), Ashley Wolff(Jenna), Jerry Lambert(Chase), Fortune Feimster(Dougie), Meera Rohit Kumbhani(Milly), Phillip Jarrell(Mailroom Mark), Jason Heymann(Prince Charming), Anthony Holiday(Coach Murray), Michelle Ortiz(Vanda), Kotaro Watanabe(Asian Businessman)