On Christmas Eve, Felice interferes in Donna and Ray's relationship by offering him a bribe to stop seeing her. Ray's alcoholic, chain-smoking mother, LuAnn, goes Christmas shopping with Donna. Differing family traditions cause tension between the Catholic Jesse and the Jewish Andrea. Clare introduces David to her father during a faculty Christmas party. They find common ground over their love of music and playing the piano. Meanwhile, Dylan manages to get in contact with his father's former fiancee and FBI handler, Christine Pettit, to help him find his stolen money, but Christine tells Dylan that the agency cannot help. Dejected, Dylan spends Christmas Eve alone and sober at his house watching Christmas themed movies on his TV and thinks back to the time when Suzanne and Erica first came into his life one year earlier. The next morning on Christmas, Dylan gets an oddball visitor who introduces himself as J. Jay Jones (nicknamed "Jonesy"), an older man who claims to be his "Christmas present" from Christine Pettit. Jones is an alcoholic ex-FBI agent and Christine's former partner in the agency who currently works as a freelance bounty hunter, mercenary, private investigator, and assassin-for-hire who was contacted about the situation and offers to help Dylan track down the people who stole his money in exchange for getting half of it. Dylan reluctantly agrees to the deal. Brandon is left alone to care for the recovering Kelly when Jim and Cindy leave town to visit Brenda in England and Valerie leaves to visit her mother in Buffalo. Kelly worries about Brandon finding her unattractive due to her fire burn scars. Also, Nat hosts a special feed-the-homeless dinner at the Peach Pit.

A motorcycle road trip inadvertently leads Brandon and Dylan to an ancient Native American ceremony where the two friends learn valuable lessons when they are arrested and subjected to community service (building a sweat lodge, which they then are invited to and do sit inside) for trespassing which helps reduce the tension between them. When Dylan gets home, Jonesy has a message for him from Mexico: he's located Dylan's missing cash and sister. Meanwhile, Valerie becomes interested in Ray and sets her sights to bag him behind Donna's back as she continues to help him overcome his stage fright on the eve of the opening of the new Peach Pit After Dark club. Kelly benefits from attending a psychology workshop seminar run by a famous, crippled psychology professor named Patrick Finley. Also, Steve finally makes up with his father.