they could have had an interesting work relationship if she ever did jobs for his boss, then, because he's definitely not the best at working with people who don't hide their off-ness well; he's very it's all business can't we just pretend we're selling widgets or something why does it have to be weird?? he likes doing criminal business like legitimate business: basically on the (space) golf course, have your people call my people, etc., so the occasions on which he's worked with the more earthy types are good recipes for hilarity