Nick tries to fix things when the Darlings are blackmailed over a sex tape starring a family member. Patrick is upset over being forced to end things with Carmelita. Brian's wife gets suspicious over the Swedish orphan he brought home. Jeremy tries to keep it quiet about him and Natalie, but when they all show up at a fundraiser for Patrick things get out of control.
Tripp sends Nick to a vineyard in Italy to get information about his father's death. Nick decides to bring Lisa along to spend some time with her away from the Darlings but Freddy and Karen are following them everywhere they go. After Leticia admits she was unfaithful to him, Tripp decides to find out if all of his children are really his.
Thanksgiving has arrived and Nick George wants to spend the day with his wife and daughter, but Tripp has another idea. Tripp wants Nick to set up a meeting with Simon Elder so Tripp and Simon can talk face-to-face once and for all. Meanwhile, Letitia helps Karen try and to get closer to Nick. Brian fights to keep his ex-girlfriend, Andrea, from taking his son away from him while Jeremy goes on a first date with Sofia.
This flashback episode reveals secrets about Dutch (Nick's father) and the relationships he had with Nick, Tripp, and Letitia. Karen's intimate view towards Nick is put on hold as she takes a liking to Simon Elder. Brian's attempt to get his son takes a turn he didn't expect and Jeremy continues to hide how much he is worth from Sofia.
Nick learns Simon and Karen are secretly together, but refuses to say why it truly bothers him. Karen doesn't attend the family tradition of watching "The Nutcracker" in order to meet a mysterious person. Brian's suspension from the ministry makes him look elsewhere for a job, and Letitia suggests he go to Tripp for guidance. Meanwhile, Juliet has a visitor from the Seychelles, and Carmelita tells Patrick she thinks she's being watched by someone.
As Karen excitedly prepares for her wedding day, she is convinced that this fifth marriage -- to family nemesis Simon Elder -- is the one that will end in happily ever after. But Tripp is still suspicious of Simon's real motives and wants Nick to make one last-ditch effort to keep the wedding from happening. Lisa hopes taking Jeremy to the wedding will make Nick jealous. In other developments, Patrick hires Jeremy to join his senate team, against Nola's protestations; Brian finds himself drawing closer to Andrea as her illness worsens; and when Letitia sees Tripp paying too much attention to their houseguest, Wrenn, she realizes that this pretty, young woman has overstayed her welcome.
Filled with love for Carmelita, newly-elected Senator Patrick Darling goes against Nick and Tripp's advice and invites her to his inauguration. Meanwhile Chase defies his agreement with the Darlings and threatens to go public with his accusation that Patrick murdered his sister; Jeremy finds out that Simon has control of Nola's little brother; as Andrea's health dims, Brian promises God anything to make her well again; and Karen goes to Nick's apartment to make amends with him, but is confronted by a gun-wielding intruder.
While the Darlings are away the help will play, a reporter is insisting on finding out the truth regarding the rumors surrounding the Darlings and the chauffeur gives his version all-be-it different from what has been said. Meanwhile, the fashion show goes forward at the Darling mansion and a socialite in attendance has "words" for the family matriarch.