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So when you do these little tests, he doesn't do anything?

Well, sometimes he'll do what you mentioned, flirt a little with me. Or say something like, "don't let any guys hit on you, ha ha."
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Also, do you know for a fact that he considers your email conversations (with Chrome or anyone else) after the separation to be over the line?

Yes, he was not happy. Told me to get rid of it. Never asked me one thing though about how long, how many, who, what did you talk about, nothing. That seemed weird to me. I'd want to know. But he wanted to sweep it under to rug. The only thing he said about it was "well, I guess that somewhat evens the playing field." - referring to his leaving. And we actually were better for a few months. But nothing really changed.
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I don't really like "controlling" my wife. I've read my history, I've seen how generations of women felt miserable and stagnant through being controlled (or perhaps simply through being controlled badly or heavy-handedly), and I've long considered that something not to do to a grown woman I care about. The reactions you seem to be looking for remind me a lot of the way men were in the bad old days. I'm learning that there's a wide gulf in between that mindset and the mindset of letting them do whatever without objection, but it's hard to find that balance and some guys might not even see that there is one.

My H doesn't believe in that whole Alpha male concept. He certainly doesn't want to be like one. They are "meatheads", "stupid", and like you said too controlling. He wants us to be "equals". Well, intellectually I can agree with a lot of that. Psychologically/biologically, I don't think it really works that way. I am a smart woman. Well educated. Why can't I feel as much desire for my H as I do when I think of that OM grabbing my arm as I walk past him in the family room, throwing me over the side of the couch, and having his way with me, without saying a dammm word. That's not what a modern educated woman should liek, right? Welcome to my world. My H sure as heck can't figure me out.
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if he went through with it as a "role-playing" exercise, do you think you would respond or would it fall flat? And does he think it would fall flat?

Flat as a pancake. I don't want him to do Anything he doesn't want to do. I'm over it.
Thanks for the suggestions though.
LFL