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I think you'll learn the boundaries after you've broken them. A long time ago I went to great, great lengths to get this one girl to talk to me. Let's just say I've somewhat learned where to stop.
Whoever said you'll get a certain feeling is right. I can tell now when something feels creepy or desperate... it's just not appealing to the person, and it's not worth your time. If you have to try that hard to get them to realize you want to ride down lover's lane, they're probably not for you.
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