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Season 4, Episode 19 - My Best Laid Plans
March 1, 2005
Kylie and J.D. have been dating for a month, but she still won't sleep with him, leaving J.D. very frustrated. Turk and Carla are still going through their wedding growing pains. Turk complains that Carla always blows things out of proportion. Speaking of relationships, Dr. Cox and Janitor have a bet that Janitor and Elliot will end up together. Cox bets the Janitor his Porsche; Janitor wagers his van.

To further complicate J.D.'s love life, Molly Clock (Heather Graham) returns to the hospital. She's only back to see one of her former psychiatric patients. J.D. gets another shock when he realizes that Turk is talking on the phone to his old college girlfriend, Rosanna. J.D. takes the phone from Turk and throws it out the window. The phone makes it way back to Carla, who asks Turk why he has three missed calls from his ex-girlfriend Rosanna. He accuses her of making a mountain out of a molehill, so Carla retreats. Re Kylie, Turk advises J.D. to have some fun with Molly and then when she leaves he can re-focus on Kylie. Sure enough, Molly asks J.D. if he wants to go out for a beer. He happens to be on the phone with Kylie when she asks, but J.D. accepts Molly's invitation anyway. And Janitor seems to be winning his bet with Dr. Cox after Elliot jumps into his arms and declares him her man. Sure enough, Cox gives Janitor the keys to his Porsche. But, Janitor has his own trick up his sleeve when he tells Elliot that Cox needs to see them on an actual dinner date.

Carla realizes that she can't stand Turk talking to his ex, so she demands that he end the relationship completely. He agrees, so she thinks. When Elliot finds out that the Janitor lied to her their date, she's upset, but when he tells her that she's the only one that treats him like a real person, she calms down.

J.D.'s night doesn't end as well. When he stops by Kylie's apartment, he mentions that he had the opportunity to be with another girl, but he held off because of his feelings for Kylie. She gets angry and throws him out. He tries calling her the next day, but she doesn't respond. When Carla finds out that Turk's ex just now found out that he's married, she's furious and storms out, leaving both J.D. and Turk without their women.