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Kris Jenner & Ben Flajnik Hot Date Pictures - Kris Jenner just admit to dating 31-year old Bachelor Ben Flajnik? Nah. But she did post a selfie of she and Ben on a "date" last night. The cheeky 58-year old Keeping Up With the Kardashians mom, who recently separated from husband Bruce Jenner, took to social media last night to poke fun at a recent Us weekly cover story.