Dustin, an amiable guy, is in love with Alexis, a coworker. When she tells him she just wants to be friends, he hires his roommate Tank, a fast-talking, amoral scoundrel who has a side business: men whose women have dumped them hire Tank to take their ex-girlfriends out on the date from Hell, to drive the women back into their old boyfriends' arms. He takes out Alexis who, against her better judgment, decides she needs some randy fun, so Tank is in a quandary: take Alexis up on her offer, or stay true to his friend. More complications ensue as the wedding of Alexis's sister approaches. Tank seeks advice from his father, Dustin pursues Alexis, and questions of self-worth need answers.

The director allowed the actors, particularly Dane Cook, to improvise extensively, often diverging completely from the script. He would sometimes run 20 or more takes, letting the performers do something different every time, before settling on a few of those ideas in order to get pick-ups or close-ups. This made life particularly interesting for the principal and background actors in the scene with Dane, as well as for the prop and sound personnel.

Tank:
[sitting watching "Ghost" and crying] God, I'm a fag.

Continuity: Claire and Lizzie throw Dustin and the babysitter out of the apartment. When they are in the elevator, Dustin's painted eyebrows become real eyebrows.

Written by Adam Beltran, Rick Garcia and Evan Langford
Performed by Lady Diamond and R.G. Tilthouse