That's what makes him weak from my POV. I'm not saying that he's a cuck (at least not willingly
). It's just that he's always a follower: to his boss, to his wife. With the exception of Addison, so maybe there is some light with her. That's why he finally express himself in a explosive way at the end saying that she never listen to him. It's not that, it's the fact that HE's incapable of being assertive in different situations. As you said, he should have forbidden to come, to stay the night with the guy, to go seeing him again. What's the outcome at the end of this conversation ? I don't want to lose to you but you can do whatever you want. So again, he lacks initiative, guts, courage, call it as you want.