15 Celebrity Relationships With Bigger Than Average Age Gaps

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What matters in a relationship? The answer to that question varies based on the person answering the question. Some might say that compatibility is important while others might say they need to have things in common. There are couples who have shared goals and others who have a sense of passion that just draws them to one another. There are other things that don’t matter nearly as much. In Hollywood, as well as in other sections of the world, age doesn’t seem to be one of those things that matters all that much.

It might seem odd to think that people who are decades or even generations apart would have enough in common to marry one another or be in a relationship of any kind. Isn’t it hard to get over the idea that the person they are with could be their grandfather, grandmother or another relative of equal distance away from them in age? The age gap doesn’t seem to bother these individuals, but it makes some of those around them uncomfortable at times. They likely get a lot of stares and questioning looks when they go out—especially if they show affection to one another that shows they are a couple.


It’s not particularly surprising to have Hugh Hefner at the top of the list. He was the mascot of the romantic lifestyle that embodies younger women in bulk. In fact, he’d in serious relationships with younger women in the past and could often be found hanging out with the beauties in his magazine on a regular basis. He has pretty much been with younger women for decades and has been married twice before. His first union ended in 1959, which happens to be 27 years before his third wife was even born. People reported that Hefner married his girlfriend Crystal Harris on New Year’s Eve in 2012.

When Harris tied the knot with her ultra-rich boyfriend, she was 26—a mere 60 years younger than the 86-year-old Hefner. The pair, of course, got married at the Playboy Mansion. But the wedding followed a failed engagement the year before when Harris called the ceremony off just days before it was to occur. The couple then reconciled, said they were happy once again and then eventually did marry. It’s amazing to think that Hefner was only married three times, though he always had plenty of girlfriends from which to choose. This was Harris’ first marriage and it’s amazing to think how she got over their 60-year difference.

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