Jimmy attempts to take Gretchen on a date.
- Chris Geere as Jimmy Shive-Overly
- Aya Cash as Gretchen Cutler
- Desmin Borges as Edgar Quintero
- Kether Donohue as Lindsay Jillian
- Janet Varney as Becca Barbara
- Todd Robert Anderson as Vernon Barbara
- Allen Maldonado as Paul Jillian
- Shane Francis Smith as Killian Mounce
After a faux pas involving Gretchen's period, Jimmy tries to make it up to her by taking her out to an expensive restaurant. The date starts awkwardly, then Becca and Vernon show up, causing Gretchen to flee before they see can her with Jimmy.
They abandon the restaurant and take Chinese food to a showing of Ferris Bueller's Day Off. Jimmy attempts to bring more attention to his book at a local bookstore, irritating the manager (played by Stephanie Courtney), and accidentally abandoning his adolescent neighbor Killian there in the process. Edgar has to find Killian and return him home. Gretchen steals the bookstore's cat, named "Kerouac".