re: Shortage of economically attractive partners for unmarried women to marry

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This honestly just sounds like nostalgia. You're just wanting something you no longer have.

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There’s some nostalgia at work there.

We’re always going to compare the girls we meet though. In this case, the comparison really stood out. I could feel the weight on her shoulders.

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The disappointments and failures? That's called life. The bolded part can sum up your feelings. It sounds like you weren't as interest simply because the older woman sitting across from you didn't stroke your ego as much.

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Sure

Anaïs Nin wrote that men like younger women, because of the way a younger woman looks at them. I think that’s true. Besides the biological advantages to dating a younger woman, it does feed your vanity and ego.

Dating someone my own age has other pitfalls too, it makes me feel old for one. There are also the biological disadvantages, which are probably drive our underlying preference for younger woman.

All of my girlfriends have been in their early to mid twenties.

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That's really a lot to expect from someone that you had just reconnected with after decades since grade school.

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I wasn’t physically attracted to her, which was strange to me. And so spent the next couple of days trying to figure out why.

In so far as I understand myself. And I can be honest with myself. I really think it was age, and the way that influenced her behavior. She wasn’t the young optimist anymore.

I didn’t want to date someone like myself.