The Walshes celebrate their seventeenth anniversary, but Cindy feels dissatisfied because Jim is neglecting her for his work. She has a chance meeting with old flame Glen, a talented artist. The two spend a lot of time together, and share a kiss after Glen's opening. Brandon and Brenda take part in a college study on twins, but are distracted by their parents' marital problems. David becomes the new campus DJ after Steve chokes in his tryout.

David invites Steve, Kelly and Donna to his grandparents' luxurious Palm Springs home for President's Day weekend. He is embarrassed to find that his grandparents, who he believed were on a cruise, are actually at home. David meets a strange girl at a gas station and asks her over to the house. She brings friends for Steve, who is still trying to win back Kelly. Brenda plans to spend the weekend with Dylan, but cannot remember the name of his hotel. She loses her wallet and spends the night in a linen closet. She finally makes it to the hotel, only to find Dylan hanging out with another girl. David's grandparents give the teens advice about romance, and help Brenda and Dylan. Brandon befriends a young customer at the Peach Pit, but later catches him trying to steal cash. The boy reveals that his family is homeless.

Chris, the acting teacher, asks Brenda to perform a scene with Andrea to bring her out of her shell. Brenda admits her crush on Chris to Andrea, who soon develops her own interest in him. The girls take Chris on a tour of the city, and Brenda is devastated when he seems more impressed with Andrea. Chris and Andrea share a good-night kiss. A jealous Brenda slaps Andrea hard during their scene. She forgets about Chris when Dylan returns home from Hawaii. Chris decides to move to Los Angeles permanently, but reveals that he has a girlfriend. Brandon refuses Jim's help as he purchases his dream car. He ends up blowing all of his summer earnings on a lemon. Jim takes pity on him and pays for the necessary repairs. Kelly and Steve lament the imminent end of summer vacation.

Music: ""Little Bitty Pretty One"" by Thurston Harris (#6, 1957); ""Joyride"" by Roxette (#1, 1991); ""The Hukilau""; ""A Summer Song"" by Chad & Jeremy (#7, 1964)

Dylan cannot stand the fact that his free-spirited mother, Iris, has moved in with him. He begins drinking, skips school, and spends all of his time at a pool hall. Brenda resents Iris for abandoning Dylan as a child, and for trying to step in and control his every move. Cindy, however, forms a bond with Iris and joins her for a number of new-age experiences. Brandon tries to watch over Dylan, who loses a lot of money in a pool game and is beaten when he can't pay off the debt. Although she wants to be a part of her son's life, Iris realizes that her presence is only hurting Dylan. She decides to return to Hawaii, and sets up a trust fund for Dylan with money Jack had once paid her to stay away. Brandon takes Dylan to an AA meeting. After Donna displays a knack for picking stocks in an economics assignment, Steve talks her into investing in the market with him.

Music: ""Mother-in-Law"" by Ernie K-Doe (#1, 1961); ""Born Under a Bad Sign"" by Albert King

Kelly finds drugs in David's bedroom. She moves in with Dylan and takes Donna with her. Howard fires David from the radio show and orders him to find a new supplier. Donna goes against Kelly's wishes by covering the rent for David, who cashes the check and uses it for drugs. Jesse breaks up with Andrea after she shares her plans to have an abortion. He later reconsiders, and Andrea reveals that she has decided to have the baby. They announce their engagement, much to the surprise of their friends. The girls enroll in one of Lucinda's anthropology classes. Dylan buys out Joey so that the Peach Pit can stay in business. Brandon pouts because he did not get to be the hero. He provides comfort to the divorcing Lucinda.

Music: ""What a Wonderful World"" by Louis Armstrong (recorded in 1967; #32, 1988)

Kelly suffers a miscarriage, and learns that she may not be able to have children. Donna worries about her finals; David adds to her stress by pressuring her to let him move in. Donna panics during a final and runs out of the classroom, costing her a chance to graduate. Professor Langely gives her a second chance by offering an oral final exam. Donna passes easily, and Professor Langely tells her that she has a future in the fashion industry. Rush refuses to give Steve a post-graduation job at one of his companies. Chancellor Arnold accepts a teaching job in France, and Steve fears that Clare will go with him. She decides to stay in Los Angeles and seek a future with Steve. Valerie angers Kelly by meeting with her father. Bill delivers the shocking news that Driscoll is no longer his employee; he has stolen all of Val's money. Kelly again pressures Brandon to evict Val, as she and Brandon plan to live together.