Because he showed no interest in listening to her, even in the beginning when she is actually trying to turn him down nicely. This is also Hitch's core message -- women fall for guys interested in THEM, who listen to them. It's not rocket science.
The only thing Chip did right was have the confidence to approach her. Which was why she was also extremely nice when she first turned him down -- she acknowledged that it takes a lot to approach a stranger in a bar, and she appreciated the attention, then politely told him she wasn't interested. I thought it was a pretty nice speech actually.
Then it really falls apart as Chip (as others noted) is not listening to her AT ALL and in fact rudely first starts simply spouting off cheesy physicalities "You have great eyes/lips/etc." Then when she still politely asks him to leave, he insults her, asking what's wrong with her, why she's so guarded, etc.
She wasn't interested in him. She politely said so. If he'd smiled and thanked her and walked away, I could have looked past the cheesy intro and respected Chip a little. Instead he ignored every single word she said, continued to talk over her, and became a little creepy when he would STILL not take 'No' for an answer.
In a way, Chip was an important moment in the movie because he's a shadow of the sleazebag guy who wants to "hit and quit" her friend -- he doesn't see the woman as a person, just as something he wants on his own terms.
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"I keep thinking I'm a grownup, but I'm not."
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