Dogfight (1991)

A young Marine named Eddie Birdlace (River Phoenix) is set to spend his last night in San Francisco with his military friends before they are deployed to Vietnam in 1963. Eddie and his friends plan to attend a cruel bar event called a "dogfight," which requires Marines to bring unattractive dates who will be judged for their ugliness. Eddie encounters a shy, frumpy girl named Rose (Lili Taylor) whom he brings to the dogfight but finds himself falling for as the night goes on.