Set in San Francisco in 1963, this highly original and thought-provoking drama chronicles the brief relationship between a young Marine who is about to be shipped out to Vietnam and the rather plain aspiring folk singer who teaches him a few important lessons about life and the treatment of women. The lesson begins after the Marine (River Phoenix) and his buddies, wanting to celebrate their last night of freedom before sailing off to war, decide to rent a bar and hold a "dogfight," an odious contest in which the Marines compete to find the ugliest date. The winner will get all of the other soldier's money. Not pausing to think that the whole contest is cruel and degrading to the women, Eddie Birdlace sets off to find himself a pug-ugly girl. He comes up with waitress Rose Feeney (Lili Taylor) who is only plain. A sensitive girl who listens to folk music, writes poetry and herself aspires to sing, she isn't really that interested in Eddie, but out of pity agrees to be his date. Unfortunately, as they get to know each other, he begins to have a prick of conscience. Still they go to the party. When she learns the truth, she is angry and leaves. Now genuinely sorry, he takes off after her to try and make amends.