- Photo: Jen Lowery/Splash News3 of 12
Okay, so maybe Hef tends toward younger women, and in multiples, but maybe that's the case because he hasn't met an age-appropriate match? We're thinking the 84-year-old might benefit from a more stable sweetie, who maybe might know who Billie Holiday is. And while Betty has officially (and repeatedly) denied that she appeared in those topless photos in the '40s, we don't think a hook-up with the Playboy king is completely out of the question. Oh, the stories they'd have.