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The concept of a cougar is that an older woman dates a younger man in an obligation-free arrangement that is great fun for both parties the concept of the older woman is still something of a taboo, whilst people think nothing of a man dating a woman half his age. 10 rules of dating a cougar there is nothing in the world like dating a cougar: women who've gotten more confident, sexy, and attractive as they've gotten older if you're young and single, we suggest finding one for a fling or two.