[gumpzilla]

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Guys,

She has introduced him to the boyfriend. The most likely course of affairs at this point is that she assumes (correctly) that Bob knows she has a boyfriend. We are past the point of not mentioning the boyfriend.

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Again, it was just like "Hey, this is soandso." Not "hey, this is my boyfriend." She hasn't told him anything along the lines of having a bf, I'm not sure why she would just expect him to have gotten it from that one encounter.

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So they have a planned activity and she shows up unexpectedly with some random guy in tow? I think most people would make the jump here, and she'll expect that.

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Also, she indicated interest in going up and hanging out on the roof of Bob's apartment with Bob. tbh I can't imagine her not wanting Bob at this point.

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It's conceivable, but it could easily go either way at this point. Acting all flirty and [censored] is a great way to get attention even if you're not after sex, and plenty of girls seem to enjoy a good friendboy. If he's going to have a chance, I think he needs to cast it in a light such that it looks like a romantic outing, and I think the easiest way to do something about it is to say "What will your boyfriend think about that?" Not to mention that she's going to leak all kinds of information based on how she responds to that question.