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On the night of the senior prom Natalie Miller, a homely Brooklyn adolescent, tells her parents that she must meet her date, a medical student, at the Staten Island Ferry. At the docks she surveys disembarking passengers, half hoping her imaginary escort will step ashore. Later, when supportive Uncle Harold, a retired Navy pharmacist, marries buxom Shirley Norton, Natalie's self-confidence is shattered. Although she enrolls in college, she is expelled for political activism. Desperate for their daughter's future, her parents bribe an aspirant optometrist to date Natalie. Discovering her parents' investment, Natalie buys a Honda, rents a Greenwich Village apartment operated by eccentric Miss Dennison, and gets a job as a waitress at the Topless-Bottomless Club. While riding to her flat in the dumbwaiter, Natalie attracts the attention of David Harris, an artist and architect, and they become lovers. Invited to popular Betty Simon's wedding, Natalie is delighted to discover her classmate pregnant and the unsuspecting groom abysmally ugly. Drunk with pleasure, she rushes to Harris' apartment and jumps in his bed, unexpectedly disturbing his wife. Horrified by the realization that her lover is a married man, Natalie confronts the architect. Although Harris suggests that he divorce his wife and live with Natalie, the young woman rejects such dependence and returns home.