Can I just say, and I'm just being honest...

[Athene]

CIJSAIJBH...

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You tell me I’m a “ten”, then you follow by mentioning one of my flaws and how you don’t mind it, because you’re 40 and old enough to know what things really matter. You tell me your friends can’t wait to meet me in your home state, then you warn me that the short guy is into -taller and skinnier- so he won’t be attracted to me. Did I ask? What makes you think it ever crossed my mind that your friend could like me that way? When I’m worried about my flaws (the usual one that make me unhappy) you notice and bring them up, followed by “you’re perfect for me”.

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And I can’t tell what this is. 

My guess, since you've implied that this is sort of a pattern: 

"This" is what's known as "negging". It's an intentional, calculated practice and indeed quite purposeful...And only manipulative shitheads do it.
He revealed his hand to you that night years ago, when he made a "joke" about liking insecure hot chicks who could be easily mindfucked/kept in line.

Only he wasn't joking.

You're an extraordinarily beautiful woman, J a c k. Any decent mate wouldn't feel that you need to be "taken down a peg or two" before telling you that.