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

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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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16 Responses to “Sean Penn, 59, and Leila George, 27, attended his 2020 CORE gala together”

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  1. Pineapple says:

    When Charlize kicks you to the curb and you are afraid of women your own age.

  2. AnnaKist says:

    Erghh. I wouldn’t be seen dead with this nob. Oh, wait. Yeah, that’s right. I’m too old for him… Relief.

    • Joanna says:


    • Regg says:

      I’m surprised he doesn’t hide…people still aren’t too happy about the el chapo thing…and when I say ppl, I mean ppl aligned with chapo who would make him disappear, no matter how famous 😶

      At least her dad is Vincent D…you knw if Sean Penn breaks her heart, Vincent could do some serious damage 🤗

  3. Laura Hunt says:

    Aw. Taking Poppop for a night out. He’s a ludicrous little man.

  4. Joanna says:

    I used to get upset when guys my age dated younger women than me. Now I realize they did me a favor. Thank God for my wonderful husband who is 6 months younger than me 😊

  5. StormsMama says:

    I follow Leila on Instagram and have always loved her father Vincent D (swoon)
    She is gorgeous and actually looks a lot like both her mom and her dad.
    These pics of her here with hideous bangs and dirty dishwater hair color do her no favors. The only thing I find really concerning about her is that she smiles cigarettes. Ew.
    I love her and think she’s talented beautiful and seems nice. But obv she’s a twenty something who thinks she kknows everything how else do you explain dating Sean Penn and smoking cigs!
    Hoping she ditches him soon. I think he’s aging her.

    • BeanieBean says:

      I agree, she has features from both parents. I also think she looks like Glenne Headly as she was in Dick Tracy.

    • fatladysinging says:

      Vincent D’Onofrio! Yes, Ma’am! I will watch anything with that man in it.

  6. Lady Baden-Baden says:

    Hahaha Julia Roberts’ face in that last photo confirms everything I ever suspected about being up that close to Sean Penn!

  7. Tiffany says:

    I think Leila is the spitting image of her mother, Greta.

  8. Jessica says:

    The least he could do is shoot some Botox into that baked forehead of his.

  9. Nuzzybear says:

    Left their “Totally Not Creepy” t-shirts at home, I see…

  10. Jolene says:

    I think the people of Haiti will be thrilled that he won’t be running around Port-au-Prince with a gun strapped to his thigh anymore.