Pros: He'd be a very tender boyfriend who would want to get to know his partner and how he can make them happy. Despite the icy demeanor, he's a very kind person to the people he cares about.
Cons: Sometimes he can be too subtle when it comes to expressing his emotions and feelings, and on occasion things can fly over his head when it comes to flirting. There might also be times when he has to put work and head of everything.
Cons: He's insecure and might think that his partner will realize that they're too good for him and will leave him, and he can have problems with jealousy.
Cons: Unless his partner is in on it, he keeps a secret double life as the leader of the Dark Brotherhood, not to mention he frequently goes out and does stuff that could get him killed
Pros: He can treat his partner to what they want, since he has plenty of money, and in general he's a very tender person Cons: Sometimes he can get busy with political and family affairs, and can't always make room for date night.
I'm just sitting here picturing the rapid shift between icy fleet admiral and tender boyfriend going on for thrawn when going from 'i am doing my job' to 'i am with my lover'
Cons: Sometimes he can get busy with political and family affairs, and can't always make room for date night.