My wife's last boyfriend (with whom she had been living with for a few years before breaking up with him; big mistake on her part, IMHO) was a big Danny Gatton fan and one of the last things he got back from her after their break-up was the Danny Gatton autographed guitar that he had won in a radio contest. Don't know why she had it, but she did.
I don't bring up this past relationship with my wife, but when she's talked about it, I don't understand what went wrong; He was stable, didn't have any vices, made decent money, and his family (including one who goes to our church) all loved her, and she seemed pretty involved in his circle of friends and family. She didn't end it because of me; she had broken up with him before we ever met. I met him once early on. He seemed nice enough and wasn't ugly. Go figure.
Why do you think it was a big mistake that she broke up with him? I'd be too curious not to ask her why she ended things with him, but I'd wait for her to bring him up, and then I'd ask. That way she opened the door to the conversation regarding him.
Self-deprecation is my go-to move; I was being tongue-in-cheek. TBH, though, my 'flaws' don't make me the easiest guy to maintain a relationship with and when we started dating, my financial status was very unstable to put it nicely, and my prospects weren't great. On paper, this guy seemed a much better 'catch' than me. If he had a 'flaw', it was that he wasn't church-going enough for her liking, since that's where we met.
In another twist of fate regarding her ex-BF: I was working at a golf course when I met my wife, and not long before I met her, a guy that was added to my group to make a foursome shanked a tee shot that drilled me in the arm. It didn't cause any damage other than leaving a bruise. Now we fast-forward a few months to when my wife and I are dating. Turns out he had been one of her roommates and friend of her ex. We crossed paths because he was a plumber by trade and she called him to fix some plumbing problem in the townhouse she was living in at the time. It took us a minute to recognize each other, but then we both had a good laugh about it.