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The #1 cardinal rule is: Don't ever try to figure out guys! It won't work. I can't even understand women sometimes and I am one, so I'm sure as heck not going to get anywhere close to figuring out guys.
That said, there's other fish in the sea. I know you said you care about this guy, but he sounds a little wishy-washy. Don't you want a guy who's up-front and knows what he wants?
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