Dogfight (1991) on Netflix

Plot summary

On November 21, 1963, Lance Corporal Eddie Birdlace and three fellow Marines arrive in San Francisco for a single day of leave before shipping out to Okinawa. That night the men plan a dogfight, a party at which each of them tries to turn up with the ugliest date, a scheme the women know nothing about. Eddie walks the streets without luck and slips into a coffee shop, where Rose, a waitress taking her break, is strumming a guitar. She is plain and shy rather than ugly, and when he invites her to the party she agrees, though she is unsure of his motives. On the way to the bar Eddie decides he does not want to go through with the trick, but then they run into one of his friends and his date at the door.