Jimmy Shive-Overly bitterly watches as his ex-girlfriend Becca gets married to her husband, a doctor named Vernon. As the reception goes on and he dances with her, Jimmy accuses Becca of passive-aggressively rubbing her new happiness into his face and gets thrown out of the wedding reception. He then meets Gretchen Cutler, the best friend of Becca's sister Lindsay, who tried to steal a gift in the hopes of getting a food processor. 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, who is married herself and is trying to get a job, and asks to be let out of the car. At work, she finds that her client, rapper Sam Dresden and his pals Honey Nutz and Shitstain, 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. Gretchen promises to get him some drugs, but also forces him to apologize to the photographer for making such a mess.
Later, Gretchen returns to Jimmy's house to get her purse and has an argument with Jimmy, which ends with her telling Jimmy their hook-up last 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 the house of her on-off lover Ty Wyland, a Hollywood movie producer, to get the drugs for Sam. She has found that Ty isn't as attractive as he used to be. She and Jimmy start talking over the phone and realize they want to see more of each other.
Tropes
- And That's Terrible: Gretchen tries to get Ty to tell her the worst thing he's ever done. He replies that he's trying to avoid negativity, and she continues that she once set her high school on fire to get out of a math test. Ty looks at her like she's grown a second head and asks, "Why are you telling me this? That's horrible!" It gets even better when she tells Jimmy and he cracks up laughing.
- Tempting Fate: Becca demands that Jimmy finish his insult at her wedding.
