Looks like Hef's business advisor told him it would look bad for the 'world's most eligible playboy' to be all broke up over being jilted, so he picked Ms. January for his new tootsie-roll :P.
BTW, he's 85 now - time to change his title to 'world's oldest play-geezer'
He really looks like he's got Alzheimer's or something, at least in the later pix.
And as to his claim-to-fame of championing women's freedom, there's an expose out by one of his former playmates, stating that in order for house bunnies to get their weekly salary, they would have to meet with Hef and he would go over in detail what he disliked about them and order them to improve. Guess he had to be the controlling daddy figure..