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IMHO, I think she might be a bit too young to have any sense to test him on his confidence or his abilities as a mate. She's just a child and I find it hard to believe that she has had enough experience to set him up like this. If anything, I'd said that her comment, "it probably would never happen" is a sign of her insecurity as a young female. I think she's trying to get the inside scoop on your buddy and is fishing for information regarding his feelings towards her.
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