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Dr. Phil explores the controversial trend of older women dating much First, Pie, a 58-year-old self-admitted cougar, has been dating 24-year-old Oleg for “The youngest man I dated was 20, and I was 50, and he asked me out,” she says.

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A friend forwarded me a Denver Post article on “Cougars” last week: Similar to the seeks out a much younger man (often 15-20 years younger) for sex and fun. dating a younger man: a 30-year-old woman who dates a 25-year-old guy is a 

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