The winners and probably all-time champions in this category are Crystal Harris and Hugh Hefner who - despite some highly-publicized bumps along the way - didn't let their 60 year age difference prevent them from getting married last year.
With some couples on our list you may not have realized that the man and woman are from different generations. No one ever talks about the 14 year age difference between Matthew McConaughey and Camila Alves, for example.
And, of course, as it's been since the dawn of time: men get a pass on cradle robbery whereas women get criticized for even the slightest age gap.
That's why we were sure to include Jennifer Lopez and Demi Moore to make this an even opportunity list of borderline creepiness.
Sure, Ashton and Demi broke up in 2011, but as the original Hollywood GILF, Ms. Moore deserves credit for paving the way.
So whether you'd like to feel better about your own weird love life or marvel at the stuff celebrities get away with, check out the gallery and try to imagine all the awkward conversations these guys had with dads their own age.