Dogfight (1991)

In 1963, the night before the 18 years old "Birdlace" Eddie and his friends are shipped to Vietnam. They play a dirty game called 'Dogfight': all of them seek a woman for a party, and who finds the most ugly one, wins a prize. Eddie finds the lonesome pacifist Rose working in a coffee shop. She's happy to accompany him - but then she sees through the game. However by this time he already learned to like her, so he follows her home. Will he manage to win her heart despite their differences?