Jimmy and Gretchen find themselves falling for each other despite their better judgment.
- 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
- Brandon Mychal Smith as Sam Dresden
- Darrell Britt-Gibson as Shitstain
- Allen Maldonado as Honey Nutz
- Shane Francis Smith as Killian Mounce
Jimmy is thrown out of Becca and Vernon's wedding reception. He meets Gretchen, who is running off with one of the bride's gifts. Discovering that they feel the same about long-term love, the two hook up that night, vowing that they will never become a conventional couple. Usually Jimmy's conquests are gone by morning, but Gretchen stays and meets Edgar, who is cooking breakfast for Jimmy.
Late for work, she gets a ride from Lindsay who is astonished she slept with Jimmy. Gretchen gets annoyed with Lindsay and asks to be let out of the car. At work she finds that rapper Sam Dresden and his pals have wrecked a Photographer's studio during a photo shoot. Sam blames her for being late and insists she find him some drugs to make up for it. She returns to Jimmy's house to get her purse and has an argument with Jimmy, which ends with her telling Jimmy the night was a mistake and he was lucky to get her.
Later Edgar tells Jimmy that Gretchen must be special because she spent the night. Jimmy finds that Gretchen has taken his car, and calls her. Gretchen is at Ty Wyland's house to get drugs for Sam. She has found that Ty isn't as attractive as he used to be. She and Jimmy talk and realize they want to see more of each other.