Say you're interested in someone who has substantial power/authority over you, and you're interested in them. How do you make a connection with them that is not only based on that professional relationship. How do you cross that "ethical" boundary?
That's tough because you don't want to cross the line. I think your best bet is to try and get a work happy hour or even host a work party. Invite a few people from your work so it isn't awkward and either go to a happy hour or invite a few people over for a BBQ or something. You can get to know him then, and it will be so much easier after that to talk to him about non-work related things and maybe go to happy hour alone after that.