There’s so much incorrect with this post. Woody was a simp, not an incel. How can he be celibate if he has a girlfriend????
Their relationship wasn’t weird, it was based on co-dependence. She needed him to get out of her financial situation (which she eventually did) and she was his motivation, his rock. See how she was ready to pop Wesley when he showed up at their apartment? A ride or die.
She wanted him to do better in life but his addiction to gambling/hustling ended up with her losing him. “And sometimes when you win, you actually lose.” She said out of her own mouth “I don’t want the money stupid, I want you!”
The apex of this movie was Woody dunking the ball. He won. Wesley got his money back that he was robbed of, but Woody lost his girl in the end: a pyrrhic victory.
Wesley was a hardworking man, despite Woody making aspersions about him because he’s black. “Black men would rather lose and look good than win and look bad.” “How many dinners did that chain set your family back?”
Wesley assuming Jimi Hendrix’ band was was white. Telling Woody he couldn’t “hear” Jimi simply because he was white.
The whole movie was about dispelling stereotypes. Rosy Perez was a smart, intelectual Hispanic woman, Woody was a goofy looking white boy that could play ball and Wesley was a hard working married family man, hence the title of the film.