It's 1963 and four young Marines are spending their last night stateside in San Francisco before shipping out to Vietnam. The night's festivities include a dogfight: the Marine that finds the ugliest "date" and brings her to a party being held later that night wins. Flippant, coarse, and handsome Eddie Birdlace (River Phoenix) isn't having any luck finding an appropriate date until he meets Rose (Lili Taylor), a shy ugly duckling waitress who worships folksingers and hopes to one day join their ranks. Charmed by the young Marine, Rose agrees to attend the party with him, unaware that she's a candidate in the cruel contest. When Rose inadvertently finds out why she's been invited, Birdlace's conscience gets the better of him, and he is determined to make amends by taking her out for a night on the town. As they wander the streets of San Francisco, this unlikely pair begins to fall in love.