It is weird that Jess is one of honestly the only women Matt's hung around in the Marvel Universe who he hasn't hooked up with (except maybe She-Hulk). The list is ridiculous - Black Widow, Misty Knight, Echo, Elektra, Typhoid Mary... I can't remember if he hooks up with Colleen Wing or not too, but it wouldn't surprised me. I just read Daredevil: End of Days and it was hilarious to me that when Ben Urich looks into Matt's life, he basically finds a trail of his enraged exes (all of whom have suspiciously red-headed children with no fathers).

I don't even think Stark's track record reads quite like that (although it's also substantial and will likely include Spiderman's Mary Jane soon).