The perils of the billionaire dating pool

Dear Jack, so you want to date a rich older woman? Even in Europe and America, a substantial age difference will still elicit quiet questions and knowing looks. The reverse holds true too: society will question the motivation of a very young woman who dates a much older rich man. Relationship motivations are not always pure. Do you really love her or you see a financier of your business ideas and ventures? Do you really love her or you view her as short cut through the womb of time into the future? Same fantasy they have about dating a beautiful teacher in secondary school. Boys know these things! No car? She already has cars.

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Even as a guy, I’ve been counseled with that golden nugget of wisdom on more occasions than I can count. Growing up in a solidly middle-class family, money wasn’t ever a pressing issue. But it wasn’t exceedingly abundant, either. It was just a means to an end I knew anyone urging me on to life as a kept man at best or a gold digger at worst wasn’t totally serious — but they also weren’t totally joking. So when I tell you that I was in a relationship with a woman and money was a huge factor in our dynamic, I can understand if you assume that I was more interested in what was in her purse than what was in her head or heart.

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