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I agree with inBOIL, it really depends: Is this a good friend, did he break it off or did she, how broken up is he about her, etc?
I always go with standard: if this is a relatively good friend, ask if it's ok, no matter what. If he's just a friend of a friend, it really shouldn't matter. If this is a guy you go drinking with, always ask. Even if he's the one that broke it off and swears he's done, ask first.
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