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His Grades
We've got news for ya, girl. Your dude may not be the A student he pretends to be. Those emails to his teacher and flaking out on study dates could be because he's not doing well in school and doesn't want to let you know about it. There's no reason to pry though. He's definitely trying to get himself back on track so he can eventually go off to college. Maybe you can offer to help him out?

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