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evilbeef nailed it.
If you would call him your friend, you must ask. If he says no than it's no unless you plan on breaking off the friendship, cause if he says no and you do it anyways it's going to happen (and you're a shitty friend).
If he's a friend's friend, than she's fair game.
If he says yes, and you know he still pines for her, than it's a no.
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"Smite the rocks with the rod of knowledge, and fountains of unstinted wealth will gush forth." - Ashbel Smith as he laid the first cornerstone of the University of Texas
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