G'day Gamine, and welcome to the cellar!
If you trust your fiance, I'd say you don't have anything to worry about. The way I read it as an outsider is suggesting that the woman might be a bit of a ditz and may need a bit of guidance outside the usual. Maybe since you're involved with the business now it'd be nice for you to make contact with this woman and offer her your assistance as a woman? Show her that it's not that hard and give her some confidence.
After that, go see Bob and tell him not to be such a chauvanist in future.
