[gumpzilla]

[ QUOTE ]

But, talking to her today, she brought up an old idea they'd had about going on a wine tour. This is starting to sound fairly romantic and I'm thinking maybe Bob should hold off on prodding for information and just make a move on the wine tour because why would this chick go on a wine tour with Bob if she didn't want him?!?!

[/ QUOTE ]

Because she needs a friendboy. This would have a much better chance of success if she hadn't already introduced the boyfriend.

EDIT: To clarify, a friendboy is a person who occupies the role of a boyfriend, but without the [censored]. I mean [censored] it, this could still work out, but it seems unlikely to me. Now that the boyfriend has been formally introduced, she is likely assuming Bob is a good guy and thus safe to do friendboy activities with without any danger of nasty sexual misinterpretations.

EDIT 2: And now, I think I would reverse the field, and if I were thinking about going on the wine tour, ask her "how would your boyfriend feel about that?" to sort of put it back in the realm of datelike behavior. How she responds to that question will let Bob know if it's worth his while.