It’s November 1963. Among a group of Marines staying in San Francisco briefly before being shipped off to Asia, there is a contest: pick up the least attractive girl you can find, take them to a bar they’ve all rented out for the night, and a cash prize will be handed to the guy who brings the ugliest one. It’s called a “Dogfight”—the women being the “dogs,” if you haven’t guessed—and one of them, Corporal Eddie Birdlace (River Phoenix), is shit out of luck finding a date.

That is, until he meets Rose (Lili Taylor), a wannabe folk songstress who waits tables at a café owned by her mother. Birdlace fakes his way through a conversation about music in order to ensnare her, and she is shyly charmed. It is obvious how unaccustomed she is to the attentions of men, especially cute, seemingly confident young men like Birdlace.

After some wooing, and an initial refusal, Rose accepts his proposition. She prepares herself, albeit inelegantly, and there’s a humorous little moment when Birdlace first sees her evening get-up, and he almost can’t believe his good fortune. […]