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I can go out to the mall or something and make my intentions clear with girls I don't even know... But at school, if I think a girl is cute and we're acquaintances, I'm afraid to make my intentions clear to her. I don't even flirt half the time. What can I do to fix this?
Don't make your intentions clear. Girls like mystery, man.
You just talk. Introduce yourself and start talking. Don't focus on a date, or anything... Just talk about whatever (think of one of your buddies... how would you talk to him? Relaxed, confident and uncaring).
If she's cool - and you like her then you just say "Hey, I need to run, but you seem cool - why don't I grab your number?"
Don't mention a date... unless you're getting amazing responses from her and she's really into you -- and you think she'd be down to do something immediately (insta-date).