When Jo hits financial hard times, Jake offers to help her. Meanwhile, Jane loses her job and Matt continues his legal threads.

Jane receives a surprise visit from her sister Sydney, who has dropped out of college. Billy agrees to set up Alison with one of his friends. Jake tries to prove himself by taking up one of Jo's interests, poetry. Rhonda is furious when Terrence doesn't defend her to his snobbish friends.

Sydney continues to get on Jane's nerves and Jake reluctantly tells Jo about his meeting with her husband, Charles.

Michael and Kimberly are spotted by Alison, and Kay sends a burned-out Jane off to have lunch with Michael. Amanda propositions Billy at Lucy's engagement party.

Billy ignores Alison's wishes and tags along when she heads to Wisconsin for her father's fiftieth birthday party. He is furious when Alison refuses to share the news of their engagement. When Alison's ex-boyfriend Adam serenades her during the party, Billy announces the engagement. Adam warns Billy that the Parker family is ""weird."" Alison is haunted by nightmares after returning to L.A. Jane and Sydney's grandmother dies. Jane learns that she is to inherit $100,000, and decides to start her own design firm. Her plans are complicated when Syd and Michael seek a cut of the money because it is willed to ""Dr. and Mrs. Michael Mancini."" Michael confronts Matt about his confession to Jane, and they duke it out. Jo's potential romance with a model is quashed when he learns about her pregnancy.