Re the FF friends issue: yes, we've talked extensively about several times that the boundary issue has led to problems. Part of the problem seems to also be that he's a bit (ahem!) naive about the average female.
I think he's been through a fairly hard-learned lesson though. So have I. I think if I start to hear any particular woman's name mentioned often in regard to his work, I will pay close attention and may even ask questions.
Other than that, we've had some fairly detailed talks i.e. he says that if he's having email "friendships", having lunch alone with female coworkers, or anything else that he knows I would be ticked off about--he shouldn't be doing it in the first place.
