Leila George and Sean Penn – 31 Years

Sean Penn has come off the back of some pretty big-time relationships. This includes marriages with Madonna and a very messy nuptial experience with Robin Wright that included several divorce filings by both of them. He also dated Charlize Theron for a while, but that didn’t work out either.

But he appears to be going pretty strong with Australian-American actress Leila George. She is 31 years younger than him, and they started dating in 2016, eventually marrying in 2020. In 2021 Penn had a role in the series “Gaslit,” while George had a role in “Animal Kingdom.”