Megan becomes concerned by the amount of time Michael is spending with Kimberly. When Megan convinces Michael to ignore a call from Kimberly and spend the night with her, Kimberly suffers a seizure. Taylor discovers that the new chief-of-staff won the job because he is sleeping with Dr. Shulman. Peter uses this information to blackmail Dr. Shulman. Nick becomes suspicious of Taylor's relationship with Peter. Nick and Kyle are arrested in a barroom brawl at Shooters. Kyle offers to host Jake's bachelor party to make it up to him. Billy isn't sure that Jake and Alison are ready for marriage. Craig tries to use his expected inheritance to seduce Amanda. Roommates Syd and Samantha are at each other's throats. Billy asks Sam to move in with him. Carter continues to reject Sydney.

Kimberly persuades Michael to grant her dying wish by sleeping with her one last time. Amanda uses Craig's infatuation with her to trick him into giving her half of D&D. Craig learns that his father cut him out of the will. Peter is appointed chief-of-staff. Taylor offers to cook him a celebratory dinner, but he stands her up to go to a dinner party with Amanda. A drunken and depressed Craig shows up on Amanda's doorstep, and she lets him sleep on the couch. The next morning, Craig leads Peter to believe that he slept with Amanda. A distraught Peter sleeps with Taylor. Alison and Jake are to marry in a civil ceremony, but Alison hides in the bathroom at City Hall. Jake postpones the ceremony. Alison becomes fed up with Jake's attempts to control her and turn her into a housewife. She stays with Billy and Sam, then decides to visit her sister to avoid the meddling couple. Jake believes that Alison is going to have an abortion, but she does not. Alison returns home and moves in with Aman