Forget politics (hah!). I'm fairly certain that Barack is a pretty cool guy to hang with for awhile.
Trump, I would probably be stabbing someone in the eye within minutes.
Hilary, I'm not really sure. It would probably mostly be awkward silences.
I think I'd agree (and I didn't vote for Obama). He seems like a guy with whom you could strike up a conversation over a few beers about a lot of non-political things, like sports, and he has a good sense of humor. I get the impression that Trump would just want to talk about himself, and Hillary would just want to talk policy, and neither strikes me as having any meaningful sense of humor. I can't hang with humorless people.