The Life of Barbi Benton: Hugh Hefner’s One That Got Away

She Almost Shut Hef Down

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Benton was just an extra on his show, but Hef was so taken by her that he eventually promoted her to host. Apparently, that’s one of the perks of having a media mogul totally smitten. Surprisingly, she nearly rejected him before he had a chance fall in love.

On the second day of filming, the then-42-year-old Playboy mogul asked 18-year-old Benton on a date and she hesitated because of their 24-year age difference. Initially, she told him, “I don’t know, I’ve never dated anyone over 24 before.” Hef replied “That’s all right, neither have I.”