Why did he meet up with her for dinner? This makes no sense. The OP should end all communication with this woman and work to forget that she even exists. This is how I handle ex's.
Sounds like you've been through a lot. I'm just trying to be objective, but perhaps this pattern is due to the way you place the perspective in a relationship. Are you putting so much emphasis on the girl.. trying to make her happy, trying to be a good bf, etc.. that she gets complacent? Sounds like it may be the case. You want a girl that'll complement you, but don't make her the focal point of everything. That way, she'll respect you more and you guys can have 2 collaborative successful lives together instead of an unhealthy co-dependency. You're not the victim here, you're an F-ing man.. and a damn good one from what it sounds like. Now go out and find someone that makes you happy and don't lose sight of who you are by making her your world. Remember, its a joint-venture, not a one-sided relationship.
Tell her that she is washed up and henceforth you will be dating nubile girls in their early to mid 20's. Then instruct her not to contact you, as you will be contacting her if necessary. Then say "TIA" or "GOOD DAY."
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That does make it a little more bizarre. She considered you not mature enough, even though she CHOSE to go with a younger man in his 20's ? You might as well have told her you're TOO mature for me and held that against her the whole time Not saying its you at all, but immature can sometimes be decoded as "you're not financially 'mature' enough"