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 recluta a Valerie para que le ayude a él y a Jonesy a llevar a cabo un plan en Punta Brava, México, para recuperar su dinero perdido después de encontrar a Kevin y Suzanne. Jones y Valerie se hacen pasar por una pareja en un hotel resort donde entablan amistad con Kevin y Suzanne (también conocidos como Karl y Kitty Cavendish) para averiguar más sobre el lugar donde guardan el dinero robado de Dylan. Pero cuando Dylan quiere rescatar a su hermana Erica, Jones se echa atrás, dejando a Dylan llevar a cabo un intento de rescate imprudente por su cuenta. En Beverly Hills, Brandon se siente amenazado por la relación de Kelly con el profesor Finley, cuando Brandon comienza a lidiar con críticas del decano sobre la permanencia del profesor y sus métodos de enseñanza poco convencionales. Cuando Brandon conoce al profesor Finley por primera vez para cuestionar sus métodos de enseñanza, ve otro lado de Finley que se enfada con Brandon, lo cual causa un distanciamiento entre él y 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.