While Nick and Eddie head to New York to find Owen, who left town after learning about his wife's infidelities, Hannah wrestles with her true feelings for Nick.
When Nick returns from New York after convincing Owen to come home, Hannah decides to share his feelings with him. Meanwhile, Eddie has trouble expressing his feelings for Janet in public; another professor begins to be interested in Aubrey; and Physical Phil's one connection to the outside world could be cut off.
Owen wants Nick to report back to him with the details surrounding his wife's affair with Ikey. Meanwhile, Eddie is conflicted about whether he should reveal a secret that could end his business partnership with Nick, and Sam contests his mother's upcoming nuptials.
Nick is surprised when his father refuses to do the Christmas festivities in the house, and he decides to find a way to learn why. Physical Phil continues his tradition of pretending to be an architect when his parents come for a visit, which irritates his girlfriend. Eddie freaks out when Janet gives him a very personal Christmas gift. Owen and Alison end up in bed, but their happiness as a couple is soon put onto a test.
Ray successful ex-wife Christine intimidates Hannah, after she leaves the Cataldo boys in care of an old hippy friend, in order to take a veterinary tech exam. Pizza Girl begs Phil to take her out on a ride with the classic car stored in his garage. Nick sets up Ronnie with Aubrey's friend, but things change when Ronnie realizes he's in love with Aubrey.
Janet and Hannah plan a double date, but their boyfriends can't put their differences behind them. Nick's past comes back to haunt him when he tries to bid on a new project with Eddie, and the person hiring is a man named Cupcake Kid. Ikey decides it's time to reach out to his friends, and Owen is having hard time dealing with forgiveness.
Janet is worried because Eddie and her still haven't slept together. Hannah is put in a tough position when Ray tells her that he wants to adopt Sam. Nick thinks that Aubrey is keeping a secret from him.
The Commander finds out that he is having a health issue. Ray is still trying to convince Hannah to let him adopt Sam. Nick discovers that Aubrey has been secretly visiting her estranged father. Alison and Owen start dating other people.
Owen, Nick, Ronnie, Aubrey, Gabriel and the Commander take a road trip to find the girl who saved Owen's life, and The Commander uses the opportunity to remind his sons of their childhood, and to finally be able to tell them about his condition. Nick encourages Gabriel to tell the truth about his upcoming departure to his daughter.
Nick makes a shocking discovery that he is broke, while Hannah deals with her mom as she prepares for her wedding. Meanwhile, Jenny, the beer delivery girl who saved his life is asked out by Owen.
Nick, Phil, Owen and Eddie are shocked when they find out that their childhood crush, Angela Ferilli, is dead. They reminisce about the past they shared together and realize how much Angela affected their lives.
A visit from Eddie's ex-girlfriend Rory causes problems in his relationship with Janet. Nick receives a great job offer that should take him far away from Knights Ridge. Hannah is arrested for assaulting Ray's ex-wife Christine.
After Eddie's ex-girlfriend resurfaces, Janet must cope with her visit. Meanwhile, Hannah's arrest affects her engagement to Ray and Nick must decide whether he should take a job offer that would once again take him away from Knights Ridge.