Hmm. Tony and Whitney were actually functional for a while. The problem is that they have too many issues for one relationship, and things fell apart. Not to mention all the complications that arise from them being who they are: him being Iron Man and Tony Stark; her father being a giant nut bag. I think in some what if world, it could have worked out, if they'd both had some time to work their shit out, without all the comic book drama intruding. ;)

Of course, after they broke up, Whitney took a turn for the seriously crazy. Bendis writes her more like classic Whitney, and not hermit!Whitney. idek what Fraction is doing. DDD: That's some seriously old canon he's working from, especially considering that Whitney seems pretty content with and well matched by Parker. So yeah.

You know, there's an interesting story in a Whitney/Tony/Steve triangle.