15. Sandra Bullock
After her divorce from reality star Jesse James, Oscar-winning actress Sandra Bullock was spotted on the arm of Canadian heartthrob Ryan Gosling. There was a 16-year age difference — she was 38, he was 22 — and their relationship lasted just a little over a year. The two are still on good terms, though Ryan later hooked up with another cougar: Eva Mendes, who is six years older, and is the mother of his new baby girl!
Photo: People
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