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The Cougar and the Cub: 10 Rules for Dating a Younger Man. He’s looking up to you in many ways, and admiring the knowledge that you bring to the table. Dating a younger man requires patience on all yourself and your man. My pistons firing like they were back in my 30’s, but hey, he care. As long as I The Cougar and the Cub: 10 Rules for Dating a Younger Man Please note: You are currently browsing img pin by loann sheets on sexy lil dresses pinterest that is 304x750px in size. This image is listed in milfs looking for cubs category. The Cougar and the Cub 10 Rules for Dating a Younger Man, 304x750 in 27.65 KB.