I know what you are saying about OW. I really don't think there is one but when they are in "the place" they are ... who knows what will happen. I don't feel I'm there enough to fill his EN so maybe someone will come along and do it for me. Scary isn't it.
Has your H tried to "go back" in time. Mine signed up for classmates and got in touch with some old friends. So far, he has been more regretful that he doesn't have guy friends that he has kept track of. One friend of his has high school "buddies" that he golfs with and my H really thinks this is something he has missed out on. I guess the male bonding thing. I have tried to encourage him (where before I would have been pissed because I wasn't getting my quality time).It sounds like your H does go places and do things with other guys which I think is good for them. Gives them companionship with it being female.
Sounds like he does have a odd family? You sound like you handle it well and don't get upset with them (wise choice I think).
