A friend of mine was in a situation like this. We talked about it extensively a few times and I kind of figured he'd break up with her. They ended up getting married and having kids. I like her, so I'm happy for them, but I know the insecurity is still an issue and he's asked me a couple of times over the years if I can reassure her on this matter or that.
Most of the most insecure women I know are married, so I have to assume that most guys just don't care about that. I would find it difficult, personally.