I think he's just dating as he said. For all we know more than one person. He's in the Prime Pussy stage right now thanks to his win on BB and while I'm thankful that he's a tightarse who isn't going to get taken in by some harlot, I imagine he's having a good time playing the field. We saw that in those pics when they were at that GC that night when he was macking on different girls. He's going to events, traveling for Ch 9... any single person would be lapping it up.
Him and Jade will eventually find good-hearted partners who treat them right although they both might have to kiss a few frogs first. They both have good hearts which is why they're drawn to each other and will probably be friends long after they've faded from the eyes of camera snappers.