Gloria was in debt to mobsters over a car, and her plan was to sit around and drink while she nagged her boyfriend to fix her problems for her, which lead him into the seedy world of gambling & debts and nearly got them both killed. How was she a "smart" character? Why was he lucky to be with someone like that?
She was by far the most irrational & narcissistic character in the movie. Even the crazy guy that they hustle first has the heart to correct his path when he's half way through an armed robbery. She showed with her "thirsty/water" metaphor that she understood/believed that filling a need temporarily (drinking & telling herself her boyfriend would fix everything, then getting angry at him when he couldn't) was worse than fixing the real problem (paying off her debts and learning how to have a healthy relationship), but her actions didn't reflect her beliefs at all. She had no integrity to her own beliefs so there is no way to take her seriously, she was either delusional or extremely dishonest with herself. I thought it was represented perfectly in her last scene on the boardwalk. She is confronted with the choice to help the 2 people who got her out of her horrible situation and into a life of monetary security by getting her on Jeopardy, and she turns her back on them when she's finally in a position of power for the first time in the film. Even when Billy tries to appeal to her emotions she just puts on her walkman and roller-skates off into the sunset like an oblivious airhead, off to live with the fairies in crazy sociopath land forever. She was a cold, dark & horrific character, and if you can relate to her on any level I worry for you :O
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