Have you ever failed with a girl, where another guy did great?

I have a friend who is pretty similar to me, similar likes/dislikes, taste in music, body type, etc. He went out with a girl for 15 months and GOT ENGAGED to her. Then, he broke it off and she was crushed. About a year later, I asked him if it was OK if I asked her out, and he was fine with it. I did, and we went out twice, and then she said she didn't want to see me anymore. It's driving me nuts. Why would she be crazy for him, enough to be "crushed" when he broke off the engagement, but not even give me a chance??