I think with that utterance, he was responding to how bizarre and clownish she'd made herself look; she kind of upped her dogfight factor while dressing and grooming, and he's reacting to that. Nevertheless, he can see that, even with all that, she's not an ugly girl, fundamentally. Though he certainly doesn't realize it then, I think she's already begun to get to him in a way, with her sweet innocence, idealism and excitement; he's already begun to see her a bit differently, and not just as an objectified "dog." But he still has his dogfight goal in mind, and wants to make a good showing, or even win, so he tries the lipstick on the face ploy, as kind of a last-ditch effort to make her look worse. Once she's wiped it off and fixed things with her powder, she's asking him, "Do I look alright?" As he answers yes, that she looks nice, you can see a moment where his face reflects the realization that he's not going to win. I think it's right after that, that he offers the idea that they not go to the party at all, but maybe go dancing somewhere else. Both actors are so wonderful in that scene, and the whole movie.
Multiplex: 100+ shows a day, NONE worth watching. John Sayles' latest: NO distribution. SAD.
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