Sean Penn, 59, has married his girlfriend of four years, 28-yr-old Leila George

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As I get older, my tolerance for men’s shenanigans and malarkey is at an all-time low. That’s what makes me understand these May-December romances though – women in their 40s and 50s want no part of someone like Mr. Hamface himself, Sean Penn. The younger women are the only ones who will have him. They’re the ones buying his “tortured artist” bulls–t. Women past a certain age see that crap for what it is: ham drama. Anyway, 28-year-old Leila George has tied herself legally to 59-year-old Sean Penn. Ugh.

Sean Penn and girlfriend Leila George appear to have taken the next step in their relationship. The actor, who turns 60 this month, and the actress, 28, recently tied the knot, according to their friend, philanthropist Irena Medavoy.

“We are so happy for @leilageorge #seanpenn getting married. We love you,” Medavoy wrote in a celebratory social media post on Friday, alongside a slideshow of images, including a photo that showed off the actress’ blue engagement ring, as well as a pair of matching gold rings worn by the couple.

“We are over the moon to find your soul mate true partner,” she added. “You are meant to be together God Bless you both.”

Rosanna Arquette also wished the couple well in the comments section, writing, “Wonderful. 🎶 Love and light,” while Josh Brolin replied with a series of heart emojis.

The pair’s marriage comes just days after they were spotted in Los Angeles, grabbing dinner with the actor’s 26-year-old son Hopper.

[From People]

Something that’s a little bit crazy to me is that Leila seems to have taken after her mother, Greta Scacchi, entirely and she doesn’t look a bit like her father, Vincent D’Onofrio. I wonder what D’Onofrio thinks of this. Would your father approve of your marriage to a 59-year-old ham when you were 28? Oof. Anyway, congrats to Sean and Leila. I feel like this will end in disaster, but what do I know. They have legitimately been together for four years now, so it’s not some sudden thing. That doesn’t necessarily make it better though!

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83 Responses to “Sean Penn, 59, has married his girlfriend of four years, 28-yr-old Leila George”

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  1. Ceej says:

    Two years older than his son. She could actually be his daughter. Blech

  2. lola says:

    That’s the age difference between me and my mom. I know my mother would not be amused if I married a guy that was her age, so I can imagine her parents are not that thrilled.
    And then it had to be Sean Penn out of all the old dudes, I’m sure there are less problematic almost 60 year old men. I wonder how long she will be able to stand his bullshit.

  3. Noki says:

    Him and his ex wife are both ridiculous.

  4. Kiki says:

    She’s gorgeous.

  5. Biff says:

    He looks like he’s two handles and a zipper away from a handbag. Imagine what she will have to look at in 10 years. Sorrynotsorry

  6. VS says:

    She is marrying a man who is almost as old as her dad; I think Sean is 2 years younger than her own father; Sean is marrying a woman who his son could date…. LOL

    They are both adults, so they know what they are doing. I wish them all the best and a happy life!

    • Ms_TheTea says:

      @VS I checked – 11 months between Vincent and Sean.

      GROSS! Basically marrying your absentee father?!

      • PixiePaperdroll says:

        I mean… I’d go after her dad but also, I’m 45. Sean remains a ‘never’.

      • McMom says:

        Yeah, I’m surprised her relationship with her father hasn’t received more attention here. Didn’t he completely abandon her as a child? I’m no shrink, but perhaps there is…a connection? #daddyissues

      • McMom says:

        Yeah, I’m surprised her relationship with her father hasn’t received more attention here. Didn’t he completely abandon her as a child? I’m no shrink, but perhaps there is…a connection? #daddyissues

  7. AnnaKist says:

    I have but one word: Yuck.

    • You Must Be Joking says:

      Sure. She’s a downgrade from Charlize Theron. A big downgrade. But I find it refreshing that a Hollywoid celeb cares about more than just looks and is willing to be with a nice person even if she is a bit plain.

      • Biff says:


      • CherryL says:

        She isn’t plain. She’s really pretty.

      • Biff says:

        I read it as sarcastic. That she’s the pretty one and he’s the…well, you know.

      • Smadge says:

        My first thought she was that she’s really plain too. But to each their own, I guess! She also seems older than 28, she has sort of a mature vibe in photos. Plain but probably nice, and could definitely do better than him.

  8. Case says:

    Well, she’s very pretty.

    That’s all I’ve got.

  9. Watson says:

    I liked her ring as it’s understated and simple, with a sapphire solitaire. However no amount of money would get me to marry that insufferable man. God help his new young bride, and may her prenup provide her with plenty of therapy.

  10. reef says:

    I feel like if you marry an almost 60 yo man when you’re almost 30, nothing can go wrong!

    • TeamMeg says:

      LMAO – best comment ever!

    • Nikki* says:

      A 60 year old who’s been rumored to abuse women. Ugh. And an angry man. And one, according to AnnaKist above, has a face like a dropped pie.

  11. CherryL says:

    So they started dating when she was 23 or 24? That’s kind of creepy. That’s coming from someone who has no problem dating men 20 or 30 years older but I’m in my 30s. Old men dating women in their early 20s just seems weird to me.

    • Sarah says:

      That was going to be the subject of my comment, that is young to be starting a relationship with such an old guy, even if he didn’t have the baggage, ego, etc. we KNOW comes with Sean Penn. Oh dear.

  12. whatWHAT? says:

    “ham drama”


    and THAT is why I keep coming back. bravo.

    1) this will last a few more years, then kaput.
    2) I didn’t know Greta Scacchi and Vincent D’Onofrio dated and
    3) I SURE as hell didn’t know they had a kid.

    • Boxy Lady says:

      I’ve heard some interesting things over the years about Vincent and Greta’s relationship. Like it was quite passionate and torrid. Then he left her and Leila when Leila was very young and Greta had a bit of a nervous breakdown because of the break up. I don’t think Leila had a strong relationship with Vincent in her early life. I might be off on some details, though.

  13. stormsmama says:

    I adore Vincent (her father) and encourage ou all to follow him on instagram. He is the most lovely burly man. Yum.
    She actually did get some of her fathers looks- she is a perfect combo of her mom and dad-
    she is beautiful. Have you seen her on Animal Kingdom? I enjoy her on that show a lot.

    As for her marrying Sean Penn: EW…EW! And soul mates? Really. UGH

  14. Liz version 700 says:

    Ham drama is a perfect quote! This guy literally scares women into running away and ghosting him. Best wishes to the new Ms. Penn but keep a burner phone handy.

  15. Otaku fairy says:

    Wasn’t Charlize in her early 40’s when she dated him? I’m not so sure if it’s about being old enough to see Sean Penn for what he really is. Everything I’ve heard about him from sites like these make him seem undateable and like a shit human being, so it would be a no. Plus he’s fug. She’s well into her 20’s. For a woman, that’s ancient by ‘cancel culture’ standards, so to me it’s not about her being too young, it’s the fact that it’s Sean Penn.

    • bettyrose says:

      I agree there’s two different issues here: 1. much older man. 2. Sean Penn. But I’m curious how this relationship started with her at 23-24. She’s not some bumpkin with dreams he picked up at the bus station. She hardly needed Sean Penn’s help with her career, so what could possibly have been appealing about him to a beautiful and well connected 23 year old?

  16. AA says:

    “As I get older, my tolerance for men’s shenanigans and malarkey is at an all-time low. That’s what makes me understand these May-December romances though – women in their 40s and 50s want no part of someone like Mr. Hamface himself, Sean Penn.” 10000 times yes.

    • bettyrose says:

      Doesn’t Charlize Theron basically omit her relationship with him in any discussion of her life?

  17. Jenn says:

    I think she looks a lot like Young D’onofrio in profile (same jawline and button nose!), but from straight-on she looks astonishingly like her mom. She’s a really pretty young lady.

  18. Lala11_7 says:

    I will NEVA get pass the fact that Greta Scacchi married her FIRST cousin and has a grown son with him…

    I mean….


    • Andrea says:

      I just read about that when I deep dived what happened to this woman’ s parents. She must have Really loved him.

    • M4lificent says:

      Ewww… My mom is one of 9 kids, so I have about two dozen first cousins on that side. And everybody knows that Cousin Billy is the hot cousin. But it’s not like we would have ever actually hit it….

    • bettyrose says:

      I mean it’s gross by current standards, but read novels from even half a century ago and it was totally normal to be cruising for love at family gatherings.

    • You Must Be Joking says:

      It still happens in some countries and is socially acceptable. I met a guy from Syria who married his first cousin. She passed away years ago. The last time I spoke with him he was telling me there were a lot of war widows in Syria looking for overseas husbands so they could get out of the country. He told me he was looking in to getting one. Not my thing. But hey, you do you.

      • Chrissy says:

        Yes. Greta spent most of her early years in Europe which seems much more socially liberal, so I think it’s not that unusual.

  19. Bella A A says:

    I live in SF and I saw It at a bar where he hangs out a few years ago and he literally looks orange and smells like stale cigs!!

  20. Jessa says:

    Anyone else (probably UK only…. v niche reference) think the image was of Barry Chuckle in the thumbnail – the one with the ‘tash

  21. Chaine says:

    Whenever I hear a couple described by someone else or each other as “soulmates” I also always hear Morgan Freeman in the background narrating “They were NOT soulmates.”

  22. Valiantly Varnished says:

    I have only one word: YUCK.

  23. nicegirl says:

    Full on barf

  24. jbyrdku says:

    I dated a guy in his 50’s once (still in my 30’s). Worst mistake I ever made.

    • candy says:

      Well, I dated a 40+ year old when I barely cleared 20. It was a manipulative and exploitative relationship, which I only realized after the fact. I don’t really judge people if they think they’re happy, but in my experience, guys who do this are usually immature jerks.

  25. Mariane says:

    Ewww another man incapable of aging & being with women his age!! I doubt this would last but I wonder if this is because she’s pregnant ?

  26. holly hobby says:

    Is he going to make her give up her career too so she can stay at home and play house? I really think whatever career momentum Robin Wright had he killed it. She struck lightening twice (Princess Bride & Forrest Gump) and both times nothing happened afterwards. She stayed at home in Ross while he fooled around. This guy is a career killer.

  27. candy says:

    holy crap, I thought he just got done dating Charlize Theron. Gossip years move fast.

  28. SJR says:

    $10 says divorced in less than 5 years.

    Has she not heard of his past behavior?
    If I was on my last $5 and Sean Penn offered to buy me lunch if I would date him..No thanks, I’d rather starve.

  29. Bobbie says:

    I would ride that for a night. I bet he’s a basket full of hell. 🙂 For a night. Not for a lifetime.

  30. L4frimaire says:

    Her parents are basically the same age as Penn. Was recently watching Greta Scacchi in the Versailles tv show, and she’s still very good. Remember when she was one of the hot prestige actresses of the 90s. Penn is such an egotistical weasel. Watched that Kate del Castillo documentary where she gets him that meeting with El Chapo and he comes across really cavalier and egotistical, which he probably is. Don’t envy his new bride having to manage his moods.

  31. AmyB says:

    I am 49, going on 50 and wouldn’t date anyone who looks like him LOL. I am not speaking of his fame, or wealth or Hollywood connections – which is precisely the reasons he lures these young women in. In addition, how can anyone be ignorant to the fact of his volatile temper and his abusive history towards women??? LOL. And yes, Charlize Theron basically negates the fact that she even dated him in interviews, which is pretty telling to me …

    I am not denying his acting ability, he has produced some great characters on film. I AM saying he is a total asshole in life, and good luck to this poor young woman. How anyone could marry someone that much older, and someone so close to their own parents’ age is beyond my comprehension. But hey, maybe that’s me. I don’t have Daddy issues lol.

  32. Jill says:

    1. I always thought Greta Scacchi was absolutely gorgeous. Her daughter is as well.
    2. An LA friend says Sean Penn is the single most charismatic man she’d ever met. Absolutely compelling. (She’s in the entertainment industry and has so many good stories.)
    3. Ew. So much.