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.