the general idea is that she would need to be at least 32+ and they were together at the very start of his career, right before things took off. they would have been together until 2007, which is when his life started to fall apart with drugs and alcohol. he bought a ring to propose, took her out to get down on one knee and then chickened out and broke up with her instead. if you're interested in hearing more details, i'm happy to make us a custom to brainstorm more as well.