Caitlyn Jenner & Sophia Hutchins – 5 Years

If you thought that the age gap between Richard Gere and Alejandra Silva was massive, it doesn’t even compare to the 47-year difference between Caitlyn Jenner and Sophia Hutchins. While it’s an example of age not mattering, it’s also helped along by the fact that there is no romance in this relationship.

It’s more like a professional friendship, as Jenner puts it. Hutchins is also a transgender woman and the founder and CEO of the odorless, makeup friendly sunscreen called Limassol. The 23-year-old entrepreneur is a former Pepperdine University student, and her affiliation with Caitlyn began in 2015.

Sylvester Stallone & Jennifer Flavin – 23 Years

Sylvester Stallone once had to sell his dog and star in adult videos because he was flat broke. We all know he stopped doing adult films, and after selling the screenplay for Rocky, he turned his career around and even bought the dog back. His relationship with Jennifer Flavin has had similar ups and downs.

In the ’90s, the relationship was on-again-off-again, with Stallone at one point leaving Flavin, via FedEx no less. But it turns out it was because he thought model Janice Dickinson was pregnant with his child, and when he found out that she wasn’t, he went back to Flavin, whom he married in 1997.