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Does he find mature, attractive and successful women intimidating? Maybe he falls for younger women because they're easier to charm an manipulate. An older women is independent and set in her own ways.
The somewhat older teacher of my computer class tried to seduce his 22 year old assistant by sending her an indecent proposal via email. I don't know if she reported him to his superior, but she was moved to a different class and decided to quit after the semester was over. I assume they bought her silence. Maybe if the teacher had money it would have been a different story. Needless to say, it proved to be a very unpleasant experience for her, and maybe even traumatic. If it had happened to us older students in our late thirties and forties, we would have laughed at the teacher and told him to f*** off.
I really do not get it but when he tells me about the drama I often think... what do you expect?