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So exactly is it that makes a guy creepy? How did he hint that he was being "more serious" while you were playing around?
I've observed this too since high school, and it appeared to me that if the guy looked like Brad Pitt or George Clooney, women are flattered by flirty behavoir, and annoyed or threatened if the guy looks like Steve Buscemi. The better looking the guy is, the forward he can be. Although as he gets more forward, more girls would be put off by it.
The irony is that when the girls aren't around, the Pitts and the Clooneys are often more derogatory in how they talk about girls than the guys they find creepy. So I concluded that unless the guy is way over the line (like grabbing a breast or something), the difference between fun flirting & creepy is how attractive the guy is perceived to be - or like the SNL video says: "Be good looking."
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