There's a business concept called "the Peter Principle" (unrelated to the game's Peter) that people rise to their level of incompetence. I think Mr. Dick just doesn't seem to be comfortable yet with his authority though he's shown moments of strength amongst his peers. (There's family dynamics, too, that seem to play a part.) Of course, he's a mumbling awkward mess with any matter with Miss Laura and Lyanna.
But, a separate comment on this release, oh, Risa, you dirty girl.
Laura, Lyanna, Mia... Just about any pretty women.
Don't get me wrong, he's not a scumbag and/or would be rapist, like so many others, but to me, he is just Peter grown up. He keeps hitting on women who have turned him down, and even worse, ones that he has power over. Luckily, he is too nice to USE that power so far, but it doesn't change the fact that he is hitting on someone, while being their superior, while she is dating someone else, after she has turned him down, repeatedly.
Them being old friends makes it less bad, kind of, but also worse in a way, since it means he has been pining for her for decades, and refuses to take the hint. Don't get me wrong, I sympathize with both him and Peter, I have been there, done that, but Peter needs an education (and a lot of hard work on himself), and Dick needs to stop shitting where he eats. If you want to pick up girls, go to a bar or dungeon, use a dating app, something, but don't hit on women at work. It rarely works out, and then you are stuck working with your ex-. Not to mention, that if it does work out, then you are working and living with your spouse, with almost no time away from each other. No matter how much you love someone, that is too much, and that is if you are peers. If one of you has power over the other, then it's even worse. lol
That said, he is still one of the better guys in the game, he is at least a 'good' alignment character and would protect them if it comes to that.