Ashley Olsen, 30, was looking ‘romantic’ with 59-year-old George Condo

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To this day, I get Ashley Olsen and Mary-Kate Olsen confused. Not just in photos (I will never be able to tell them apart, honestly), but I confuse their dating histories too. Mary-Kate married Olivier Sarkozy (brother to former president Nicholas Sarkozy) last fall. So MK is spoken for. Ashley was single-ish, although there were rumors that she had gotten serious with director Bennett Miller. But Ash and Bennett might be over, who knows? Because Page Six claims that Ashley was looking “romantic” with a 59-year-old artist.

When spies saw Ashley Olsen meeting with artist George Condo at the Mercer Hotel recently, buzz began that the pair were dating.

“It looked romantic,” a source told Page Six.

But a rep for Olsen, 30, told us it was all business. And Skarstedt Gallery, which reps Condo, 59, replied, “It was simply a business meeting. Mr. Condo just finished [an] advertisement for the Row,” Ashley and twin Mary-Kate’s fashion line. The brand recently posted a Condo sketch of its new Upper East Side store online.

With work in the collections of MoMA, the Whitney and the Met, Condo was commissioned by Kanye West to create artwork for his 2010 album, “My Beautiful Dark Twisted Fantasy.” Condo’s wife, Anna, filed for divorce in 2015.

[From Page Six]

I know of George Condo mostly because Kanye West loves his art. In addition to the Dark Twisted Fantasy album cover, Kanye also commissioned Condo to “paint” on a Birkin bag for Kim Kardashian. Kim carried that Condo-painted Birkin one time and it was pretty obvious that Kim loathed it. As for the idea of Ashley getting romantic with a dude who is nearly twice her age… it wouldn’t surprise me. I guess MK was always more into older men, but I wouldn’t be shocked if Ashley had a thing for older dudes too.

I’m including a few photos of Condo below. When I first saw these pics, I was like “why am I looking at photos of Timothy Spall?!?” Is Ashley Olsen dating Timothy Spall’s doppelganger?

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Photos courtesy of WENN.

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32 Responses to “Ashley Olsen, 30, was looking ‘romantic’ with 59-year-old George Condo”

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  1. LaraK says:

    The bag Kim got is the funniest thing I have seen in a while. I needed the laugh today.

    I think both MK and Ashley are all kinds of screwed up, but their relationships are not hurting anyone, so whatever. Their business practices on the other hand… yeah, not so harmless.

    • Rocío says:

      Please tell me more about their business. I know they are “fashion designers” but that is as far as my knowledge goes.

    • meme says:

      kimbo doesn’t wear that hideous bag anymore, does she? I wonder where she keeps it.

  2. HeidiM says:

    his fly is down in that last pic.

    • Imqrious2 says:

      Omg I had to go back and check lol. Gave me my first laugh of the day! Thank you, HeidiM!

  3. Guest says:

    I don’t know MK and Ashley don’t bother me at all. Sure there looks to be something off, but they are cool with me.
    Good for her if she’s happy.

  4. meme says:

    these two are just plain weird.

  5. Lilacflowers says:

    If Timothy Spall and Andrew Lloyd Weber had a child

  6. HH says:

    I normally rail against the idea of “leagues” and “ratings”….. but girl…. ASHLEY…. boo boo….you can do WAY better.

  7. Annie says:

    It’s like they date sugar daddies when they don’t need the money. Idk… Their guys always look so smarmy.

  8. Lucy says:

    I’ve only recently learned how to tell them apart. It’s something about the shape of their lips. As for both of them being into older men…I tend to atribute it to the fact that they’ve been working ever since they were babies, and have matured faster than most people their age as a result, which could be why neither of them is interested in guys their age.

  9. serena says:

    Damn I forgot MK was married..

  10. Original T.C. says:

    Thing is, the Olsen twins have very old faces for their age and men are very superficial. I won’t be surprised if younger guys were not as much into them as older guys. In addition to them maturing faster intellectually due to exposure to working with adults from age 3months upwards.

    As a young impressionable woman when you are rejected by one age group and favored by the other, you eventually learn to appreciate the group that favors you and then start spending more time with them. This is my theory about the twins preference for older men. It doesn’t always have to be daddy issues! It’s similar IMO to when men of another race have a preference for your particular looks and body type so then you learn to appreciate them back, spend more time getting to know them and overtime preferring them back.

    • that last part is one of my closest sorority sisters…. she was kinda ridiculed about having a more voluptuous body when she was young and white guys didn’t typically latch to that but men of color (mostly black and latino) loved it… and she learned I think earlier on to prefer them back….

      nothing wrong with that last part of Original T.C. 🙂

  11. GoodNamesAllTaken says:

    An odd little pair, those Olsen Twins.

  12. frisbee says:

    No I don’t think he looks like Timothy Spall who is lovely and a British National Treasure – I do think he looks like Andrew Lloyd Webber – who always reminds me of a slug in pants.

    • antipodean says:

      @frisbee, thank you so much for the laugh, it was of coffee spitting proportions! I needed that today. We always refer to SIR ALW as Mr Inside Out Face, but a slug in pants is hilarious, and takes the proverbial biscuit. I have also heard him described as having the face of a fried gumboot. Given what I have heard about him over the years, the outside matches the inside, so I have no qualms when he is denigrated for his oleaginous appearance.
      I concur with you that Timothy Spall is a National Treasure, I loved him in “Turner”, did you see that? It was a really quirky performance, if I remember right he was nominated for an Oscar for that part. His son Rafe is no slouch either as an actor, apples and trees it seems.

    • Starkiller says:

      You know Andrew Lloyd Webber is also British, right? Wouldn’t that make him a slug in trousers? Unless you’ve seen pictures of him in his underpants, which…ugh, I’ve just put myself off my breakfast.

      • frisbee says:

        @ Starkiller Yup he is a slug in trousers but this is a US site and I was pandering – downright pandering to the US readers on that one. Slug in trousers sounds funnier to me though… sorry your breakfast has been waylaid perhaps you can catch up on it later?
        @ antipodean – Love love love Tim Spall, he was so good in Turner – heartbreakingly so at one point, shame he lucked out of an Oscar nom but then as we all know by now, Oscars have very little connection to acting, it wasn’t a big film and they probably didnt have the millions of dollars it take to run a campaign and hire ‘opinion formers *cough* Di Caprio *cough*
        http://www.independent.co.uk/arts-entertainment/films/news/oscars-2015-mr-turner-star-timothy-spall-admits-disappointment-at-snub-9990301.html

      • antipodean says:

        Thanks for taking the time and trouble to post that article from the Independent, @frisbee. It seems that I got confused when I thought Mr Spall was nominated for an Oscar, but in fact was overlooked…again. His reaction was typically gracious, and he will no doubt go on to produce further sterling work, in spite of the snub! Anything by Mike Leigh is fabulous in my book. I sussed that you were using the word “pants” for those Americans who are reading, and I always substitute the word “trousers” in my head, so it made no odds to me. I always remember the old joke about the “jam trousers”, and it makes me laugh. Of course, you may have meant “pants” in its pejorative sense, and that also makes me laugh, so it’s a win/win. Hats, and pants, off to the Messrs Spall, major, and minor.

  13. Bridget says:

    MK is the one with the really random taste in men – Stavros Niarchos, the Katzenberg son, a couple of artists, and then ended up married to Sarkozy. But Ashley has a definite type, the guys all look vaguely similar. That alone makes me think that she’s not actually with this guy. But if she is… these women have some really random taste in men.

  14. Crackkin says:

    As they age it gets easier to tell them apart. I think MK’s a chain smoker and it has started to show on her face in the past few years.
    These women are moguls. They have been for years and it comes as no surprise to me they are attracted to older people. People who have their s**t together generally are
    older.

    • Danielle says:

      I used to be able to tell them apart easily. Hate to say it, but Ashley was the pretty one. But not anymore. Now I can’t tell them apart. Weird.

  15. Manjit says:

    He looks absolutely nothing like Timothy Spall.

  16. Sasha says:

    I don’t understand all the comments saying how odd they are? MK Olsen has certainly battled some demons in the past but they seem happy, close and are still incredibly successful.

    Unfortunately I think they are VERY easy to tell apart now. Ashley looks a lot more like their old selves. MK looks very different.

  17. Roller74 says:

    What’s with the Olsen twins and the MUCH older men they seem attracted to? It’s a bit weird, no?

  18. tealily says:

    I completely forgot about that bag!! Hahaha! HAHAHAHAHAHAHA! I see a touch of Spall, but with zilch of his likability. I mean, maybe this dude’s a lovely guy, but he’s got a fish mouth and his art sucks.

  19. MellyMel says:

    I’ve been a fan of them since I was little so I can tell them apart…it’s the eyes. Ashley has big round eyes and MK are more squinty. Also MK looks a little older I think from her past(?) health issues.

  20. jammypants says:

    They’re actually not identical twins. They’re fraternal twins.