I don't know if anyone watched him, but I remember when Alex (from The Circle) did a Q&A or something, and he mentioned how he'd 'helped out a friend from the show' a bit with some of the money he'd won or something. I think a lot of people assumed it was Freddie (who was really desperate to get veneers done), but I think it was Dan.
I really don't think them getting back together is good idea. Imo he used her and will continue to do so - especially as she still has a bigger following than he does.
I never really liked him much. He was entertaining on The Circle for sure, but the way he reacted to Alex/Kate said everything. Its not as if they'd fully flirted. Nobody from the last season was that level of pissed with James.