I think he would hang out with all of us. I think there are conservatives, who, even though they reject gays and lesbians, are very loving people. I think that their beliefs arise not out of some hatred or fear of GLBT persons, but out of assertions about the way the world should be. I strongly disagree with them, but I don't think that just because someone is anti-gay that makes them a hateful person.
That being said, I think that Jesus would hang out less with the "religious right" (and the "secular left") and would hang out with the same people described in the Gospels.
"The one thing truly worthwhile is becoming Godís friend." - Gregory of Nyssa