Is it even possible that he just doesn't understand how inappropriate his behaviour is?
He's insensitive and caught up in his own naive view of how it should work out. It's clearly inappropriate behavior in the context of your relationship with him. It doesn't sound to me like he understands or has enough experience to understand that there is a minority of other women who would welcome his behavior -- women who are looking for a no-strings-attached affair. He sounds like the typical misinformed guy who knows his boss had an affair "like this" and so he thinks his only problem is making this relationship into the same thing. He's making no effort to understand your situation and how you feel.
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I've been thinking about it and he's nearly 50. I wonder if this is how mid-life crisis manifest. Men who are otherwise decent reasonable people develop friendships with women and maybe they don't even know it's happening - and wham -
No, I think the mid-life crisis thing is way overblown and used as an excuse for a lot of stuff. People have affairs and marital screw-ups at all ages. When they happen in middle age, they're called MLC's. If they happen after 4 years, it's called the 4-year itch. If it happens shortly after marriage, it's called "it wasn't really a marriage after all". Everything has a name in retrospect.
In fact, there a plenty of people who go through middle age with no MLC whatsoever.
