Sean Penn, 59, and Leila George, 27, attended his 2020 CORE gala together

June 2024 · 2 minute read

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Sean Penn and Leila George have been dating since 2016. It was actually a complicated start to their relationship, because at the time, Penn was moving through 20-something women like tissues, but Leila was the one who stuck around. Leila is the daughter of Vincent D’Onofrio and Greta Scacchi, and she manages to not look like either of them. She’s quite lovely and I feel sorry for her because she’s dating a baked ham. They started up when she was 24 and he was 56 or so. Now he’s 59 and she’s 27. And they’re still together! Which shouldn’t surprise anyone, they were still together last year when they partied on a yacht with Leonardo DiCaprio and Camila Morrone.

Sean brought Leila to the 2020 CORE Gala on Wednesday night in LA. CORE is Penn’s charity, the one focusing on relief efforts in Haiti and the Caribbean. He’s been focusing a lot on CORE for years, although I don’t think he goes on the ground much anymore (which is fine, fundraisers are great). Penn’s kids Hopper and Dylan were also in attendance at the gala. Fun fact: Dylan Penn is actually one year older than Leila George. Also: Leila was blonde a few years ago but I guess she’s brunette now. The darker hair actually makes her look younger?

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Photos courtesy of Getty.

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