On Christmas night in 1959 Baltimore, Maryland, Eddie Simmons speaks to his friend, Robert “Boogie” Sheftell, at a party. Boogie descends to the dance hall’s kitchen, where he finds Timothy Fenwick, Jr., breaking the glass windows with his fists. Fenwick reports that he exchanged his date, Diane, with another boy for $5. Returning upstairs, Boogie convinces Diane to go home with Fenwick and reveals that he must also go home and study for law school, which he attends in addition to his job at a beauty salon. After the dance, Fenwick intentionally flips his car over, then covers himself with ketchup, pretending to be injured. When Boogie, Eddie, Laurence “Shrevie” Schreiber, and Shrevie’s wife, Beth, find Fenwick and Diane on the side of the road, they laugh about the prank and Fenwick drives Diane home. Afterward, he meets Eddie, Shrevie, and another friend, Modell, at Fells Point Diner. On the other side of the diner, a man named “Bagel” offers to call off a $2,000 bet that Boogie placed on a basketball game, since he knows Boogie will be unable to pay if he loses. However, Boogie declines and joins his friends at their table, where he convinces Modell to put money on the game. Boogie later reveals that he has a date with Carol Heathrow the following evening, and bets the boys $20 that Carol will touch his penis on the first date. Later that morning, Shrevie, Boogie, and David Frazer go to the train station to meet their friend William “Billy” Howard, who has come home from graduate school to attend Eddie’s upcoming wedding. The boys report that Eddie plans to test his fiancée, Elyse, about football trivia before he marries her. They return to the diner for breakfast and discuss Boogie’s college career at University of Baltimore. When Billy visits Eddie at home, the two friends discuss their relationships with women and Billy denies a romantic involvement with his longtime friend, Barbara Culler. During Shrevie’s shift working at the appliance store, a slightly-intoxicated Fenwick stops by to tell him that more people have bet money on Boogie’s date with Carol. That night, during a screening of A Summer Place at the movie theater, Boogie pokes his penis through the bottom of the popcorn carton in an attempt to get Carol to touch it, as Eddie and Fenwick sit nearby. When she notices, she screams and runs out of the theater; however, Boogie explains what happened, and charms her into returning back inside. Outside the theater, Billy punches a former high school bully as revenge for getting beaten up by his baseball team in eleventh grade. He then visits Barbara while she works at the local television station, but she asks to meet him in the morning after church. At the diner, Shrevie tells Eddie about his struggle to talk to Beth since their marriage. The men rest assured knowing that their friendship and the diner will always remain consistent. Boogie discovers that he lost his basketball bet, and meets the boys inside. They argue about his mishap with Carol, but Boogie raises the stakes by claiming that she will have sex with him on the next date. The friends leave the diner at dawn and agree to meet back there that afternoon. While driving home, Boogie stops to flirt with a girl, Jane Chisholm, who is riding horseback in a field. Billy meets Barbara inside the church, and she admits that she is pregnant with his child after they recently ended their six-year platonic friendship by having sex. He tells her that he loves her and would be willing to marry her, but she accuses him of confusing friendship for love. Elsewhere, Fenwick watches a university challenge tournament on television and correctly answers the questions, while Boogie phones Shrevie and convinces the boy to lend him $200 for his gambling debts. As Boogie drives over to Shrevie’s house to collect the money, Shrevie yells at Beth for misfiling his music records, and leaves. Boogie arrives to find Beth in tears. Meanwhile, Fenwick laments his position as a college dropout who refuses to work in the family business, and asks his brother, Howard, for money. As Billy and Eddie watch Ingmar Bergman’s The Seventh Seal at the movie theater, Shrevie pulls them away to retrieve Fenwick, who has drunkenly seated himself in the church’s nativity manger wearing only his underwear. When Fenwick knocks over the display, police officers arrest the boys. In prison, Billy tells them that Barbara does not want to marry him because she is devoted to her job. Billy, Shrevie, and Eddie are released from jail, but Fenwick’s parents refuse to post bail and he is forced to stay overnight. At the diner, Eddie confesses to Boogie that he is nervous to get married because he is still a virgin. Later, at the television station, Barbara again refuses to marry Billy out of convenience. Beth stops by the beauty salon to inquire about the bridesmaids’ appointments to get their hair styled for Eddie’s wedding. Outside, a man named Tank demands that Boogie settle his gambling debts by that night. However, his chances of repaying the debt are thwarted when Carol telephones Boogie to cancel their date because she has fallen ill. In the salon, Boogie and Beth reflect on their past relationship as a couple, and Beth feels that her marriage to Shrevie has caused her to lose her personal identity. When he assures her that she is beautiful, Beth suggests that they go out together that night. Later, Elyse fails her football quiz by two points and Eddie attempts to call off the marriage. Boogie takes Beth to Fenwick’s apartment and asks her to wear a blonde wig so that Fenwick will mistake her for Carol, thereby ensuring that he will win the bet. Shrevie and Fenwick hide in the closet to act as witnesses, but outside the apartment, Boogie has second thoughts and admits the scheme to Beth, who thanks him for his honesty. Meanwhile, Billy and Eddie visit a strip club and laugh about their past relationships with girls. Later, at the diner, Tank tells Boogie that Bagel paid off Boogie’s debt. Bagel says he helped out of respect for Boogie’s father, and offers him a job so that he can work off the money. At the strip club, Billy plays the piano and leads the jazz band in rock and roll music as Eddie and the stripper dance onstage. Just after dawn, Boogie reintroduces himself to Jane Chisholm and goes horseback riding with her. At Eddie’s wedding reception, Fenwick tells Diane that he plans to travel around Europe, and Boogie enjoys Jane’s company. After Modell gives a speech toasting Eddie’s friendship, the boys watch in disbelief as Elyse throws her bouquet and it lands on the table in front of them.