Donna's snobbish mother, Felice, puts Ray's feelings for her daughter to a test by offering him money to stop seeing her, while Ray's alcoholic, chain-smoking, redneck 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 who finds common ground with him over their love of music. Meanwhile, Dylan goes to his old friend, Christine Pettit, from the FBI to help him find his stolen money. Unable to help Dylan, Christine then contacts an alcoholic, former FBI agent-turned-bounty hunter/private investigator, named Jay J. Jones (Jonesy), who contacts Dylan on Christmas Day and offers to track down his money in exchange for getting a full share of it. 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. Also, Nat hosts a special holiday feed-the-homeless dinner at the Peach Pit.

On their semester break, Dylan and Brandon take a motorcycle trip through California and they end up being subjected to slave labor by a Native American sheriff for trespassing on a reservation, which helps dissipate the tensions between both of them over Kelly. Meanwhile, Kelly benefits from attending psychology workshop seminars run by a famous, psychology professor named Patrick Finley. Donna tries to help Ray get over his stage fright on the eve of his debut at the grand opening of the Peach Pit After Dark. Steve spends the weekend moping over his father, Rush, taking over the Peach Pit After Dark club from him.

Dylan recruits Valerie to help him and Jonesy pull off a caper in Punta Brava, Mexico to reclaim his lost money after they find Kevin and Suzanne. Jones and Valerie pose as a couple at a resort hotel where they befriend Kevin and Suzanne (aka: Karl and Kitty Cavendish) in order to get to know more about where they keep Dylan's stolen money. But when Dylan wants to rescue his sister Erica, Jones backs out, leaving Dylan to carry on a rash rescue attempt alone. In Beverly Hills, Brandon feels threatened by Kelly's relationship with Professor Finley when Brandon starts dealing with criticism by the dean concerning the professor's tenure and his unorthodox teaching methods. When Brandon meets Professor Finley for the first time to question him about his teaching methods, he sees another side to Finley who lashes out at Brandon which causes a rift between him and Kelly.

Kelly's continued involvement with Professor Finley and his conflict against the college faculty to preserve his tenure frustrates Brandon since he knows about Finley's hostile and paranoid attitude. Meanwhile, Valerie seeks a reward for helping Dylan recover his money and asks both him and Jones to cut her in on a large share. David's old flame Ariel Hunter, now a music company rep, returns and woos Ray to get him to sign a music deal, much to Donna's worry. Also, Andrea flirts with trouble when she starts seeing Peter while Jesse is away on business.

Donna's mother, Felice, confesses a past indiscretion to her about her involvement in the Rose Bowl tryouts of 1969, causing Donna to question her own innocence. Meanwhile, bounty hunter Jay J. Jones returns and asks Valerie for help in a divorce case he has by posing as a prostitute in a sting operation to catch the husband in the act. A revenge-seeking Ray charges Joe with battery over their Halloween encounter, resulting in Joe being suspended from CU's homecoming football game. Also, Steve tries to protect the CU mascot, the Golden Condor Head, from the rival college. Brandon mourns the departure of Dylan from Beverly Hills, and Susan encourages him to write a paper about Dylan's plight.

Carl hosts Steve's weekend long 21st birthday bash on the ship Queen Mary in Long Beach, where the music group "The Goo Goo Dolls" entertains. Carl then asks Steve a favor: to have a chance with Clare who he has had a crush on. David and Donna grow more intimate while their producer Erik, makes a move on Donna and other women as well. Andrea Zuckerman arrives in town to have fun at Steve's party, and Nat brings Joan along who keeps feeling unwell. Meanwhile, Valerie hires an FBI agent, named Richard Ballen, to find Colin who's in the area trying to get access on a ship to take him to South America. Also, Susan tells Brandon that she has decided to leave town to accept a job offer at a newspaper company in Washington D.C. which makes him wonder if he has a future with Susan after all.