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-His first wife left after 18 years because she felt like she was missing out on life? How many women do you know that leave relationships after that long for a weak reason like that?
More often than not men seem to leave their women for this reason. Seems like he's enjoyed plenty of freedom since they split.
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-He broke up with one because she wouldn't move in with him (this sounds stupid, but if it is true it highlights that he might be controlling/manipulative)
Was thinking that maybe there were legit reasons she didn't want to move in with him. Like, she found out he's not such a great guy after all.
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-He broke up with another because she became less careful of her appearance (again this sounds like an attempt to tell a quick story, but if true points to a possible superficial nature)
Sounds pretty shallow. Usually, as we get serious about someone, our attention to details (like how often we shave our legs) fall by the wayside. People, including women, have other priorities than just looking good. We have families to take care of, jobs to do, hobbies to enjoy. The world doesn't stop because some lady forgot to wax her eyebrows.
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-He broke up with the last one because she was an artist who broke dates and such? (sorry that sounds like a blatant attempt to use a stereotype to hide why they really broke up)
Artists are flaky people. Perhaps she had other priorities. If she was breaking dates, then it's a pretty legit reason, but all his others sound a bit shady.