@daredevil21134: It depends of the type of Jason Todd we're discussing. Pre 52 he was portrayed in so many different shades that it's hard to get a steady baseline on his morality (for lack of a better word). New 52 Jason and Countdown Jason would probably due better with Donna whereas Battle for the Cowl and Under the Red Hood Jason would probably work well with Huntress (Bertinelli).
I guess DT might also work out with a darker Jason as well, but I get the feeling that she would try to change him and he'd just end up bailing. Huntress is the only DC female that I believe could work with all versions of him. Rose Wilson would also be an insane hook up but I think they have like 0% chemistry with one another.
I think it would be cool if he dated someone who was darker than him. Like how Batman had Catwoman or Roy had Cheshire.
I agree with you again