Tony has had several notable relationships, some of which are still immortalized on this website, and these are the serious ones. It is missing the more recent induction of Maya Hansen and the woman from Iron Man Legacy that I can't remember her name. The most serious of all of them was Rumiko Fujikawa, who was killed by someone wearing his armor (a reoccurring theme) and there are a slew of failed love interests that either end up failed by Tony's own compulsions or by him putting an end to them, or being manipulated, etc, etc. They go to great lengths to ensure he's single, essentially. He also dated Jan Van Dyne for a while, until she found out that Tony Stark and Iron Man were the same person, but for a while, it was good. With...most of his relationships it starts out good.

Anyway, in the City he's slept with Callie, Wanda, Harley, She-Hulk, Karla, uhhh, and probably others that I don't remember.