Nick discovers Karen and Simon's affair, which interrupts a Darling holiday tradition; Letitia advises Brian on his recent career woes; Lisa helps Jeremy impress Sofia; Carmelita believes she's under surveillance.
Letitia's affair with Nick's father is revealed through flashbacks, and Simon and Karen flirt at the hospital while visiting Patrick. Meanwhile, Brian is busted for bribing the arbiter in his custody case, and Jeremy gets Lisa to help him continue to fake being poor for Sofia. Dutch: Peter Strauss.
Nick and Lisa's Thanksgiving plans are scuttled when Tripp requests that Nick arrange a one-on-one with Simon Elder. Meanwhile, Letitia plots to help Karen seduce Nick, and Patrick's wife demands a meeting with his transsexual mistress. Sofia: Sofia Vergara.
Karen is reluctant to marry Freddy, and Lisa suspects Karen's feelings for Nick are to blame. Meanwhile, Brian Jr.'s mother returns from Brazil, Patrick's wife finds out about his infidelity, and Natalie attempts to befriend Juliet with a song. Freddy: Daniel Cosgrove. Natalie: Tamara Feldman.
Tripp and Simon Elder face off in a high-stakes poker game, and Karen learns she can't get married until she finalizes her divorce. Meanwhile, Juliet spends time with Brian Jr., and photos of Patrick and Carmelita are used for blackmail. Sebastian Fleet: Eddie Cibrian. Sofia: Sofia Vergara.
Nick meets with Tripp's rival, Simon Elder (Blair Underwood). Meanwhile, Jeremy and Juliet's feud leads the twins to have separate birthday parties, with each jockeying for a more extravagant event. Also: Karen tries to get Freddy into a swank country club.
Nick and Lisa travel to Italy, but being accompanied by Karen and Freddy ruins the vacation. Meanwhile, Tripp learns Letitia has been unfaithful and becomes obsessed with confirming whether he is the biological father of his children; and Brian Jr. is being bullied at school.
Nick deals with a blackmailer who claims to have a sex tape featuring one of the Darlings. Meanwhile, Patrick breaks up with Carmelita, and Jeremy tries to keep Juliet from finding out about his affair with her nemesis. Natalie: Tamara Feldman.
Nick begins his quest to find his father's killer; Juliet balks at a family-photo event with real lions; Tripp pressures Patrick to throw his hat into the senatorial ring; Jeremy's latest fling is likely to incur his twin's wrath; Brian has a solution for his illegitimate son's schooling.
Lawyer Nick George (Peter Krause) reluctantly agrees to represent Tripp Darling (Donald Sutherland) and his family after the death of Nick's father. Shortly thereafter, Nick becomes embroiled in the clan's bizarre problems. Letitia Darling: Jill Clayburgh. Patrick Darling: William Baldwin.