Truth be told, we can’t get enough of celebrity relationships. We love to see who’s dating who, who just got engaged, and everything in between. We love seeing couples in love. But something we frequently scratch our heads at is when some of the most popular celebrities date people half their age over and over again — seriously, what do you talk about?

We know the “older men are sexier” is a cliched mindset as old as time, but sometimes celebrity men take on that mindset way too much and roll with it. All jokes aside, there are many wonderful, healthy relationships that have larger age differences — and that’s fine! But we can’t help but be a bit confused when celebrities like Leonardo DiCaprio, Wilmer Valderrama, and Steven Tyler continually date women nearly half their age.

Sometimes it ends with a happily ever after — like George Clooney and Michael Douglas. Or it gets, er, inappropriate — ahem, Hugh Hefner. We can’t help but question these dating patterns, and we found a lot of men in Hollywood that date women half their age. Check out which A-list male celebrities continuously date women anywhere from 10 years younger to more than half their age.

A version of this article was originally published in Nov. 2021.