Something I have observed over the years is, men have a sweet spot for upper middle class women. They are drawn to women that go to college, go to the gym, spend a bit of money on their appearance, (fake eyelashes, hair coloring, tight dresses, high heels, make up). They like women who want or have a desire to travel or be adventurous. They are more drawn to women who have the funds to take care of themselves and make themselves attractive.

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However,

Something I have observed almost universally between college and running a speed dating group is, men greatly dislike and despise upper class women. To clarify, "upper class" here means upper class for Silicon Valley. I am talking about women who come from families that own a 3-4 bedroom house in San Francisco ($3.5 million on average), and probably have an annual household income of about $600,000+. These women grow up spoiled, with the best of everything. Frequent vacations, expensive clothes, absolutely anything they want.

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Men simply don't like women this jaded and this hard to please. It makes them feel less masculine and confident because they lack the same upbringing and resources these women have.