Quote:
Originally Posted by Aliantha
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. 
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It's not even this complicated! (You women think too much!!)
Bob is making it known to your fiance that this woman is good looking, hot, a total MILF, whatever you want to call it. You have nothing to be worried about - it's just what guys do. Checking out girls is probably a topranking pastime for most.