Nick and Eddie travel to New York to try to bring Owen back to his wife and family in Knightsridge. Meanwhile, Hannah comes to terms with her real feelings for Nick.
Upon Nick's return, Hannah tells him she can't be with him. She decides to get back together with Ray and take things slowly, but Ray wants to get married. On homecoming weekend, Eddie wrestles with expressing his feelings publicly for Janet. Nick is threatened by another professor's interest in Aubrey. Physical Phil's only lifeline to the outside world is jeopardized when his TV starts to break down.
In an attempt to get over his pain and move on, Owen employs Nick to learn the details of his wife's affair with his best friend, Ikey. Meanwhile Eddie harbors a secret that could kill a business venture he plans with Nick, and Sam struggles to accept his mother's getting married.
A surprising event occurs when the estranged Owen and Alison try to figure out how to split time with their kids during Christmas. Phil lies to his visiting parents, claiming that he's an architect, which upsets his girlfriend. Janet gives Eddie a deeply personal gift, which freaks him out. Nick learns the truth about his deceased mother.
Ray's ex-wife, Christine, a successful surgeon, chastises Hannah for allowing her old hippie friend to watch her sons while Hannah takes a veterinary tech exam. Meanwhile Nick sets up Ronnie with a friend of Aubrey's on a group night out, but Ronnie realizes he's in love with Aubrey, and Pizza Girl begs Physical Phil to take the classic car he stores in his garage outdoors for a spin.
An amateur comic book Nick wrote back in high school ridiculing a fellow classmate comes back to haunt him in the present when Nick and Eddie are bidding on a lucrative new project and the man hiring is the "Cupcake Kid." Meanwhile, Hannah and Janet plan a double date that is foiled by their boyfriends.
Nick becomes suspicious that Aubrey is hiding something from him after she's overheard making a mysterious phone call. Ray tells Hannah he wants to adopt Sam, who makes her uneasy; Janet is upset that she and Eddie have not yet been intimate; and Knights ridge town is rooting for a shoo-in for the annual regional spelling bee -- except his jealous brother is hoping he'll lose.
Nick discovers that Aubrey is meeting secretly with her estranged father. Ray tries to get Hannah to commit to letting him adopt her son, Sam. Alison and Owen date other people. The Commander discovers he has a health issue.
Nick is worried about how Aubrey will react when her troubled father leaves her again, and he encourages him to tell Aubrey why he's on the run. Meanwhile, Owen, Nick, Ronnie, Aubrey and Gabriel go on a road trip to find the girl who saved Owen's life. In the course of which the Commander tries to recreate a time from the boys' childhood, before facing the truth about his condition.
In the midst of a commercial shoot to revive sales for "Best Friends' Windows," Nick learns from his accountant that he's broke. Meanwhile, Hannah's parents come to visit to help her prepare for her wedding to Ray, but the tension between Hannah and her mother escalates to a breaking point. Owen goes on a date with Jenny, the beer delivery girl who saved his life.
While Nick, Eddie, Phil and Owen have problems with the women in their lives, they learn of the untimely death of their childhood crush, Angela Ferilli. Flashbacks of the boys' lives at age 10 show the powerful effect that Angela had on them, one they discover has carried over to present day.
Eddie's ex-girlfriend who broke his heart years ago, shows up in Knightsridge to reconnect with him, which causes problems in his relationship with Janet. Hannah is arrested for assault against Ray's ex-wife, which could interfere with her engagement to Ray. Nick is offered a great job which would take him away from Knightridge and his ailing father. A previous action by one of the gang leads to a violent confrontation.
Eddie's ex-girlfriend who broke his heart years ago, shows up in Knightsridge to reconnect with him, which causes problems in his relationship with Janet. Hannah is arrested for assault against Ray's ex-wife, which could interfere with her engagement to Ray. Nick is offered a great job which would take him away from Knightridge and his ailing father. A previous action by one of the gang leads to a violent confrontation.