Tobey Maguire, 44, and girlfriend Tatiana Dieteman, 27, went for a walk in LA

Tobey Maguire and Tatiana Dieteman get in a Afternoon Walk

One of the gossip stories which always stuck with me and changed how I perceive certain celebrities was all of the stuff around Molly Bloom, the woman who ran an underground poker game for celebrities and A-listers in LA. Bloom had a lot to say about Tobey Maguire – who was a big reason why Bloom hosted the poker games – and all of Tobey’s friends, including Leonardo DiCaprio and others. But the worst stories were always about Tobey Maguire and how he was (and is) a giant a–hole, a controlling, money-obsessed douchebag.

Although Tobey was married for a decade to Jennifer Meyer, he remained part of Leo’s P-ssy Posse all that time. Leo and Tobey are especially close, and I’ve even heard stories about Leo being close to Tobey’s kids. I have to imagine that Leo was probably pretty happy when Tobey and Jennifer split up in 2016, even if Jennifer was pretty popular within that crew of bros as well. But finally, Tobey and Leo would get to hit up all the clubs together, and the P-ssy Posse had new energy!

Well, yeah. That happened. Tobey eventually started dating Tatiana Dieteman in 2018. They’ve apparently (??) been together ever since. They stepped out in LA over the weekend for a walk/pap stroll. She’s allegedly 27 years old but she looks younger than that. Tobey is 44 years old. Leo would tell Tobey that rules are rules, and this woman is over the age of 25 and it’s time to wind that sh-t down. But I get the feeling that Tobey doesn’t have to follow Leo’s rules. The power structure within the Posse will never fail to be fascinating to me. Leo is clearly the “king” of the Posse, but I suspect Tobey is the power behind the throne.

Tobey Maguire and Tatiana Dieteman get in a Afternoon Walk

Tobey Maguire and Tatiana Dieteman get in a Afternoon Walk

Photos courtesy of Backgrid.

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28 Responses to “Tobey Maguire, 44, and girlfriend Tatiana Dieteman, 27, went for a walk in LA”

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  1. Aims says:

    He gives me bad vibes.

  2. Kamala says:

    It’s great that the guys in the posse never give up on love no matter how many times their hearts get broken.

  3. line says:

    She looks like 15 or 17 years old, so the image that sends back is a father (or an uncle) and his daughter walking in the street.

  4. BAddie says:

    It’s hard to trust someone who has looked like a disgruntled senior citizen since his twenties! Like, if heebie-jeebies was a man on a walk with a toddler, this is that!

  5. emmy says:

    God, I remember when he was THE thing. I loved him on screen and then he kinda vanished. Not vanished but stepped back until The Great Gatsby. And then vanished again. In my meaner moments I wonder whether his ex-father-in-law punished him for being a douche. Or gambling too much while being a douche.

  6. Michelle says:

    Can anyone fill in the blanks on why this guy is a douche/a$$hole? All I have heard about him is that he plays a lot of poker and stepped away from the Spider-Man roles because of previous back issues. Somebody spill the tea.

    • DS9 says:

      The tea is linked in this very story….

      • Kaiser says:

        lol people never read the links

      • whatWHAT? says:

        it’s funny…not only did I click the one link about Molly Bloom, I clicked like…three more links from pages that linked FROM that link. I reviewed all the Maguire and Affleck history there!

    • Ariel says:

      See the movie Molly’s Game.
      He’s a real piece of crap.

    • ennie says:

      I don’t recall much, except he wanted a waitress (or a woman with a similar service job) to bark just because he wanted to, he was paying.
      The story really painted him in a terrible light, most probably deserving.

      • Justwastingtime says:

        And lots of random comments from people like me who met him in a kids playground in LA (didn’t recognize him).

        His kid had approached my child and a friend and asked to swing on the tire swing with them. So, being a normal person , as you have to lift them up to get in the swing, I asked where her mom or dad was and she pointed to him . I went over to make sure it was okay..

        He was with a friend and literally treated me like I passed gas in front of them, the sneer was epic.

        I asked my friend if she knew who the ass-bro dad was thinking he was a local. She cracked up and told me he was Spider-Man.

      • ennie says:

        disgusting man.

      • whatWHAT? says:

        and, Justwastingtime, if you HAD just lifted his kid into the swing, I can’t even IMAGINE what his reaction would have been. “don’t touch my kid, WTF is wrong with you?!” etc…

    • Rachael says:

      Happy to help. I watched the movie “Molly’s Game” recently and there’s a character, Player X, who is a movie star. A bit of googling revealed that this character was based on Tobey Maguire. I have to say it is unusual to get actual real information on a famous person that explains what it is that makes them despicable.

      If it is true (and by all accounts it is accurate by Hollywood film standards) he’s a sociopath – he is a very good poker player, which is fine and indicates some intelligence I guess, but he was playing with huge amounts of money, like it was confetti.

      In the movie, Player X says something to the effect that his hobby is to “ruin people”. When one of the other characters gets into trouble with gambling losses, Player X brokers a deal to cover his debts which basically meant the guy had to cover his own losses but pay Player X 50% of any winnings, meaning it was all but impossible to get out of debt and Player X would effectively “own” him. It’s usury basically and completely unethical. And Maguire apparently did broker a similar deal with a gambling addict who was part of their game.

      I read up on the story after and apparently Maguire dragged di Caprio to a poker game once and Leo spent the whole game listening to music on headphones and showed little interest in whether he had a winning or losing hand. It kind of made me like Leo more.

  7. sherry says:

    I guess his a-hole ways caught up with him, because when is the last time he worked?

  8. Valiantly Varnished says:

    I never got what was the appeal of Tobey. I think he’s an okay actor but outside of that I don’t get it. And I has no idea he had such a bad rep but Im not all that surprised tbh.

  9. Jess says:

    Ugh, he’s always grossed me out.

  10. MellyMel says:

    She looks 18, which isn’t her fault, but geez. I’ve never gotten his appeal.

  11. Anna says:

    A beautiful girl with a bloated, pasty has-been. What else is new in Hollywood?

  12. Shoshone says:

    It looks like the “ugly” on the inside is finally showing on the outside.