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A socially awkward college student must deal with two lively manifestations of his split subconscious while attempting to get over an unrequited crush on his straight best friend.

Forced out of retirement by the mob, Sam Westman returns to the world of underground bocce ball one last time.

Andy's family is falling apart, but he's in denial. To further avoid the conflict, he goes out for a drive, but is quickly forced to take some responsibility.

Brandon runs for vice president alongside Josh and does great when he steps in and gives a speech in Josh's place. Their campaign is threatened, however, when Alex Diaz - their opponent's campaign manager - uncovers the unpublished article that Josh wrote about Brandon the previous year, detailing Brandon's tutoring of D'Shawn and alleging that Brandon took tests for D'Shawn. Donna asks Clare (now attending C.U. as a sophomore) to move into the beach apartment in David's place, but Clare brings a bad snoring habit with her. Meanwhile, Valerie secretly decides to pursue Dylan after finding Brenda's mementos of him in the Walsh's garage, and hides her connection to the Walshes from him.

Emily has been accepted to the prestigious Cousteau Institute in France, but does not want to attend because she and Brandon are in love. Brandon observes her passion for marine biology and encourages her to pursue her dream. Brenda balks when she is asked to appear nude in an experimental campus play. The frat and sorority pledges must endure a series of humiliating experiences during "Hell Week." The upperclassmen order Steve to steal a prize autographed baseball from Professor Randall for a scavenger hunt, but he gets caught. Andrea breaks up with Dan and begins dating Jesse. She learns that he is a UCLA law student who attended undergraduate courses at Yale.

Donna and Clare find Kelly's stash of cocaine in their beach front apartment, prompting her to move out to Colin's for an increased drug binge. Despite Brandon's intervention, Kelly refuses help and brushes everyone off. Joe's heart condition again comes out when he collapses after a biplane flight with Jonathan, Brandon and Steve. But Joe does not want anyone else to know because it might jeopardize his football career. Meanwhile, Valerie's old friend, Ginger LaMonica, inconspicuously returns to Beverly Hills and breaks her deal by blackmailing Valerie by revealing about the jewelry theft scam for money. Valerie refuses to pay, until Ginger offers another option: a sordid night with David.

Dylan makes summer plans for a trip around the world with Kelly while Brandon counters with a marriage proposal, forcing her to make a decision. Donna tries to cope with Ray's growing hostility as they confront their differences. Meanwhile, Andrea and Jesse go through a tearful going away party at West Beverly high school before leaving town to go to Yale. Also, Jim gets a promotion which means moving to Hong Kong.

In Palm Springs, Brandon reacts coldly to Kelly after mistakenly thinking that she and Allison are more than friends; he considers surrendering to Valerie's advances toward him. Things get even worse for Brandon after he's arrested for driving Valerie's car when he's pulled over by a traffic policeman, who finds Valerie's marijuana stash in it. Meanwhile, Steve finally learns Elle's secret of being "more than a woman." Donna decides to give the possessive Ray a second chance, and rudely blows off Valerie, revealing she's figured out that Valerie seduced Ray. Also, Tom Rose and his thugs threaten Dylan with death when they catch him phoning agent Christine Pettit to make a background check of Mr. Rose, for they know something about Dylan's father's murder. This prompts Dylan to terminate his partnership with Charlie and return to Beverly Hills, determined more than ever to find the mobster who ordered his father's killing.

Donna tries to make up with David, whose increased drug use turns her away. David also steals $150 from his father to buy more amphetamines for himself. When his drug dealer is arrested later, he finds himself in possession of a huge stash of narcotics and calls on Dylan for help. Meanwhile, Jesse and Andrea meet with her grandmother to get her blessings before their wedding and reception at the Peach Pit. A dangerous affair begins between Brandon and Lucinda, who shows her true colors when she starts teaching her anthropology class of human sexuality and preaches the need for multiple partners, seeing sex as her personal weapon. Brenda gets a surprise visit from a long-absent Stuart on Valentine's Day.

Steve begins community service at a retirement home and meets Saul Howard, an ex-entertainer with Alzheimer's disease, whom Steve confides in with his problems. Dylan asks Jesse for advice when he is told to appear in court over his car accident. Meanwhile, Valerie returns to Beverly Hills after spending a sunny Christmas vacation in the Caribbean, instead of visiting her mother in Buffalo, which prompts a cold response from Kelly who openly admits to everyone that she despises Valerie and doesn't trust her for a second. Ray declines a request by Donna to perform at the opening of the Peach Pit After Dark nightclub. While working at the hospital as a resident intern, Andrea has a run in with an attractive doctor named Peter Tucker.

The Walshes trip to Hawai'i doesn't go as planned when their plane is turned around due to technical problems. A woman claiming to be Jack McKay's mistress shows up on Dylan's doorstep with her daughter in tow. David's sexual frustration leads him to be hostile to Donna. A lonely Kelly cracks her tooth on candy and calls Mel for dental advice. Jesse takes Andrea with him to church for midnight mass. The characters all flash back to previous Christmases over the course of the episode.

Jim sets a lonely Brenda up on a blind date with Stuart Carson, the son of his business associate and both he and Brenda hit it off. Dylan decides to buy a new car, regardless of the price. Due to his late night schedule, David causes problems with Kelly and Donna over his lack of housekeeping. Kelly tells Dylan that they should start seeing others as a result of her growing relationship with John Sears. Meanwhile, Andrea finally loses her virginity when she and Dan move beyond being "just friends."