Tobey Maguire’s newly-single mid-life crisis is proceeding by the book


During this holiday, please spare a thought for poor Tobey Maguire. Tobey and Jennifer Meyer announced their split back in October – they had been married for nine years, and they have two small children. I’m not going to say that they were Hollywood’s Golden Couple or anything, but they were well-liked and well-connected. Their kids call Leonardo DiCaprio “Uncle Leo” and Jennifer is pretty much friends with every mom in Hollywood. Soon after they announced their split, everyone was like, “I bet Tobey is mid-life-crisis-ing and wishes he had Leo’s life.” And yes, there were rumors that Tobey was already hitting up the clubs and acting like a single guy. And now this piece of news from Page Six:

Tobey Maguire is enjoying the single life. The actor, who split from his wife of nine years, Jennifer Meyer, in October, was spotted at Catch in LA on Monday night next to a pretty blond model. A source tells us it was “not a date,” but rather a 16-person dinner party that included Leo DiCaprio and Jonah Hill — who sat with Maguire and the babe.

Sources tell Page Six Maguire’s previously been seen around LA with other blond models. He seems to be taking a page from DiCaprio’s playbook: The newly single “Spider-Man” star’s become a fixture at clubs such as 1Oak and has been hanging with DiCaprio’s so-called “Wolf Pack,” which includes Lukas Haas.

[From Page Six]

The thing about it is… this is a bad look on Leo, but we’ve come to expect it from Leo. This is all Leo has ever been, the Senior Wolf of the Wolf Pack, the Alpha of the P-ssy Posse. Leo has spent the last twenty years doing this. But Tobey was the one who settled down with a nice girl, had babies and seemingly stepped away from all of this. So is it just a standard-issue mid-life crisis (Tobey is 41 years old) or is it something else? Like, Tobey just seems like the P-ssy Posse version of Scott Disick. The mess who doesn’t realize that he’s a mess. The guy with small children who still wants to party like a 21-year-old. Just buy a sports car, dude.


Photos courtesy of Fame/Flynet.

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68 Responses to “Tobey Maguire’s newly-single mid-life crisis is proceeding by the book”

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  1. MunichGirl says:

    He’s kinda creepy.

    • Ladybird83 says:

      There’s always been rumors following him about a serious gambling addiction, maybe his wife got fed up? Never been a fan.

      • MunichGirl says:

        Yeah, he’s just like Ben Affleck when it comes to gambling.

      • Kate says:

        At least he didn’t get a “phoenix rising from the ashes” mid life crisis back tat

      • MunichGirl says:

        The tattoo is fake and for a movie.

      • zxc says:

        I’ve disliked him ever since I stumbled upon a bunch of comments about him, possibly even on this site? Several people described how mean and petty he was, I think one of them worked at a casino he used to visit.

        ETA: See Ramona’s comment down below.

    • StartupSpouse says:

      I think the Lainey blind riddle about the newly single guy who sends d–k pics to his hookups, and none of them have cared enough to go public with them, is about TM.

    • Katenotkatie says:

      God, he did not age well. Remember The Ice Storm and Pleasantville and Cider House Rules? The late 90s were all about Tobey. It’s kind of funny but mostly sad that so many of the hot young actors from those days have just…not maintained.

      • hunter says:

        I never thought Tobey Maguire was hot, just average. Average dude in movie looks. Which is fine, because he played compelling roles and did a good job. But never thought he was hot.

    • sensible says:

      ….and homely.

  2. Veronica says:

    It’s pretty sad when you’re non-famous – albeit well connected – ex-wife is the more interesting partner in the breakup.

  3. Danielle says:

    Does Tobey even work anymore?

    • jmo says:

      He has a new movie coming out 2017 (The Boss Baby) but I don’t think he really cares about acting anymore. He’s made enough money with Spiderman.

      • Bitchy says:

        Google says Maguire’s net worth is $75 mio. That won’t last forever if he keeps living the high life. He just bought a house for $13 mio. And the old house sold for less than $5 Mio. So Maguire is going big???

      • zxc says:

        >Google says Maguire’s net worth is $75 mio. That won’t last forever if he keeps living the high life.

        Depends how that 75 mln is allocated. Maybe he has a bunch of fancy rentals.

  4. Margo S. says:

    That photo of tobey is so perfect. And can i say, this whole “pussy posse/wolf pack” thing is getting kind of redundant. I mean, this has been going on forever. Is leonardo going to be 60 years old at 1Oak?! That last sentence I wrote made me laugh. I think it might happen!

    • littlemissnaughty says:

      I was going to say, NEVER use another photo for any TM posts! 🙂

      I always thought he’d go the Clooney route later in life. But Clooney was always so much classier about his life choices and didn’t seem embarrassed by them. Not sure if Leo is embarrassed but he should be. He can live his life the way he wants to but the Wolf Pack is too much for a grown-*ss man.

      • zxc says:

        > But Clooney was always so much classier about his life choices and didn’t seem embarrassed by them. Not sure if Leo is embarrassed but he should be.


        Leo can’t even pull a VS model anymore. Not for the lack of trying though I’m sure.

  5. I Choose Me says:

    Excellent choice of pictures. Leo despite his modelizer ways does not strike me as sleazy. Tobey however, gives off such a sleazebag vibe.

    • Sunrise says:

      Really? DiCaprio screams sleazy.

      • HadleyB says:

        He never made the public believe he was anything other than partying, dating models and acting, and he has many interests other than booze and coochie.

        Tobey is just a sad sad man who wanted to be this, than that, and has no identity.

        what else does he do but gamble, drink and pay young girls to be his date? He barely works and even when he does we never remember what it is, and he has no other interests or hobbies at least Leo does and tries to fight for the environment and wildlife and never tried to be this ” good guy” or America’s guy pal.

      • minx says:

        Leo likes models, they like him. He’s single, he can do what he likes.
        I used to think Maguire was just sort of a harmless guy. Now I think of him as a homely, mean douche who has no career anymore.

    • Ramona says:

      Your Tobey suspicion is confirmed by the Blackjack dealer who wrote in her memoir about how Tobey ordered her make animal noises before he would tip her.

  6. Rocio says:

    His face screams D-BAG!

  7. Sally says:

    I just think about that article about how tobey treated those girls at their poker tournaments made me forever dislike him

  8. OSTONE says:

    Since I read how he treated the poker game hostess, this douche canoe has been in my naughty list. Sayonara, 2nd best Spider-Man.

  9. Louise177 says:

    I had to chuckle that because he sat next to a model Tobey is a pig. If anything was going on I would think there would be more details. Maybe a mid-life crisis but at least he doesn’t seem out of control and sleazy.

  10. Talie says:

    The only thing I like him in was Pleasantville and Cider House Rules…beyond that, no.

  11. Aenna says:

    He looks like he’s been eating shit out of a hairbrush in those pics.

    • I Choose Me says:

      Never heard that expression before but can I just say, ’tis a thing of beauty. *adds to my insult file*

    • Kitten says:

      He looks like he smelled a fart but the pics are amazing. Seriously giving me life.

  12. ell says:

    hahahah his face. what is he famous for now? he hasn’t done a movie since like, 2006 (and if he has, i missed it).

  13. mia girl says:

    Me thinks it comes down to that old saying:

    “You can take the boy out of the P*ssy Posse
    but you can’t take the P*ssy Posse out of the boy.”

  14. MrsBPitt says:

    I seriously, do not mind Leo D. with his models…He isn’t married, doesn’t have any kids, so as far as I’m concernd, he has the right to party with his “pussy posse” until he is 90! Who cares?? Tobey, on the other hand, needs to grow up! He has children to think about…Is it me, or does TM just have the most “I’d love to smack him in the face” face, ever!!!!

    • Kitten says:

      I tend to agree. The modelizing doesn’t exactly make me respect Leo but it doesn’t bother me in that it’s his choice to live that lifestyle. As you said, he’s single and presumably these models know what they’re getting into with him.

    • minx says:


    • I Choose Me says:

      Backpfeifengesicht. German word. Definition: a face that cries out for a fist in it. 😀

    • Chingona says:

      Exactly, I have no problem that a man or woman who is single wants to party and date tons. But Tobey has two children and should be over the Wolf Pack lifestyle. When you have children that you decided to bring into this world they deserve better than to see their parents hooking up with randoms and hungover all the time. I am not saying you can’t have fun and go out but be responsible about it.

      • Fanny says:

        But what did Tobey do that’s not responsible? I saw a bunch of pepaws and a blonde sitting around a table. Presumably, Tobey doesn’t have sole custody of his kids so they were probably being taken care of by their mother (who also spends a lot of time with Leo, including spending Thanksgiving with him).

        I saw it implied that the divorce was because Tobey’s career has dried up and he has “nothing going on” while his wife has a thriving business and social life. Being single might not be his choice, so going out and meeting women doesn’t seem unforgivable to me. I do find it distasteful that so many people have no qualms about needling him for his career misfortune.

      • N says:

        He was making out with a young looking model, there is a video of it and he is literally eating her face and even when she is pulling away and trying to leave, he pulls her right back several times. He was all over her.
        Feel sorry for his ex and kids if they see that video.

      • Bridget says:

        Tobey gets needled because his career downturn is a direct result of his notoriously poor attitude. He’s an infamous jerk.

      • Bitchy says:

        Well, Tobey is single and his children were probably taken care of. It is his life after all.
        But I do think he should be criticised for cavorting with his new lady love so publicly. He should be discreet as his children might see that and what will they think? I don’t think that publicly kissing you new girl leaves a positive impression wíth the family of your ex-wife and keep in mind that that family is actually aunts and uncles and grandparents to your children.
        Not classy.
        Nobody expects him to remain single. But be discreet for your children’s sake.

        Btw. does anybody know why Dicaprio sold so much of his properties lately and even at a loss?

      • Fanny says:

        I’m curious about Leo’s home sales as well just because it’s a bunch of properties all of a sudden. Leo has always been notorious for being extremely careful with his money so I don’t think it’s money troubles.

        There is his Palm Springs house (did he ever really use that?), the Malibu house his mother has always used, and a weird little ranch house in Studio City that I would imagine someone else in his family has been using.

        He just cut the price on the Malibu house, but he’s still selling it for four times what he paid for it.

  15. smcollins says:

    I used to find him so adorable. Not anymore!
    But I still love him in Pleasantville and Wonder Boys.

  16. tracking says:

    He seems like such an @ss.

  17. BeBleu says:

    I remember reading an interview Rashida Jones did years ago where she talked about being in a relationship with an emotionally abusive actor at the start of her career, and following his advice because he “seemed to know what he was doing.” Always thought she was referring to Maguire.

  18. Ruyana says:

    Everything I’ve ever read about him anywhere says he’s a really creepy, nasty guy with zero regard for other human beings. Oh, and gambling addiction.

  19. Allie B. says:

    I don’t know why everyone gives Leo such a hard time about his dating preferences. I would watch him read the dictionary. He is a stellar actor and all of these models know exactly what they’re getting when they bed him. A selfish lay and a 10 day boyfriend. It’s not like he’s some abusive womanizer.

    • Fanny says:

      I think Leo’s great – wonderful actor with a lot of integrity, smart, funny, charming, well-spoken, devoted to his family. For me, it’s a bit of a blemish on his personality that he chooses to spend all of his time with 1) friends who are by and large known to be immature douchebags and 2) a parade of interchangeable Victoria’s Secret models that he seems to treat as disposable.

      It’s just that he’s got so much potential, and then there’s this unsavory side that makes me think less of him. He’s not hurting anybody and there’s no need to hate on him, but I feel like I’m just rooting for him to be a little better.

      And I would like to see him have a meaningful, stable relationship at some point, just for his own benefit. I kind of feel sad because sometimes I think the womanizing (and cheating that goes along with it) is compulsive and not just recreational.

  20. Rebecca says:

    I thought that, at one time, he was a recovering alcoholic. If this is true, he is off the wagon ans there is probably more mess to come. I’m sorta expecting more dishelved drama from him.

  21. serena says:


  22. Kriz says:

    I have always always alway thought he was an overinflated ego, with a slack jaw and mediocre talent. Never understood the appeal.

  23. Dial Side says:

    Amongst people I know who’ve spent time with him, the rumors are that he’s been physically abusive to women. My BFF used to work with one of his exes, and I remember my friend passing along stories about his physical abuse too. I didn’t necessarily believe them because secondhand info about celebs is kind of horseshit, but when they’re combined with his Pussy Posse membership and the book that mentions he made a female card dealer bark before he tipped her . . . Eh, they’re kind of believable.

  24. Etienne says:

    Worrisome developments.

  25. artistsnow says:

    I LOVE that sneer picture. Thank you!! Shows his true colors.

  26. Zach Taylor says:

    You commentators need to shut up Tobey is going through something and so what if he wants to go out and party like a 21 year old its his life and so what if he wants to date girls that’s his choice and by the way he’s a badass actor.