I'd meet up with his wife and have a nice cosy little chat, over coffee with her..
Also, 'past' seems to refer to everything that happened more than 3 months ago, but thats not really the past. She is the same person, same sexuality, and shes going to do the same stuff - 'hookers ball' and all. I dont think you can handle it..
I'm not saying that a guy who feels insecure about what he looks like is not someone who should be sympathized with. It feels like crap for anyone who's struggling with this. But, GENERALLY, boys have traditionally been taught from early childhood that their real value comes from what they DO and who they ARE, not how they look. Unfortunately, for girls, it has been about how she looks, and maybe how she can make others feel..