I have a friend/co-worker who I like and care for very much, but he is somewhat a sociopath and I can’t figure out a way to improve our friendship. He’s a good soul, despite his negative qualities and I think we could be good friends; I just don’t know how to propose we hang out outside of work or anything like that. Normally I’d just be casual/upfront with someone, but he’s a pretty intimidating dude and I get the feeling it wouldn’t go over well…? I hope this makes sense… Any suggestions?