Leo DiCaprio tried to be Tobey Maguire’s wingman at a club, but the girls blanked Tobey

Tobey Maguire and Jennifer Meyer split up in 2016. Their divorce was pretty quiet, and it didn’t seem like there was a huge fight over assets or custody. Everything seems pretty amicable in general. Tobey had a much-younger girlfriend a few years after his divorce, but I don’t think they’re together anymore. It seems like Tobey is single right now and looking to pick up some young lady. His pick-up lines must be pretty rusty though: “Y’all remember Seabiscuit?” and “I was Spider-Man too for a while.” So Tobey’s BFF Leonardo DiCaprio decided to help out his bro, and one of the founding members of the P-ssy Posse. Leo went out as Tobey’s wingman last week! The results were… not good.

Old pals Leonardo DiCaprio and Tobey Maguire were spotted partying together in the VIP section of nightclub MainRō restaurant and supper club in Hollywood on Thursday night.

“Tobey and Leo came to the club together for a boys’ night out,” a source tells Page Six. “It was very clear that Tobey was on the prowl and Leo was his wingman. Leo introduced Tobey to three different blondes.”

But it seems that even starring in the latest “Spider-Man” installment doesn’t attract the ladies.

“Even with Leo’s help, Tobey couldn’t land a girl,” the source continued. “None of them seemed interested when introduced.”

The duo arrived at 10.30 p.m. but called defeat less than two hours later, leaving, “because it was clear they were having no luck.”

DiCaprio, 47, and Maguire, 46, have been friends for decades and were part of a notorious group of thespian pals that dubbed themselves the “p—y posse.” Other members included Lukas Haas, Kevin Connolly and David Blaine.

[From Page Six]

Thanks, I want this to be a Hollywood movie? I want Tobey and Leo to star in a movie, documentary style, of Leo going around a nightclub, introducing himself to random 20-something blondes, bringing those blondes back to Tobey and the blondes completely blanking him. I’m laughing just thinking about it. Maybe the movie could be shown through the blondes’ perspectives. And is Tobey’s “type” really “young blonde”? That’s Leo’s type. I think Tobey would be fine with dating women over the age of 25, and women with dark hair or red hair. But who knows. Another P-ssy Posse adventure ends in tragedy!! I love that 47-year-old Leo – arguably one of the most in-demand actors in the world – is doing wingman sh-t for his bro. Leo probably loved it though. I bet he relishes spending time with Single and Ready to Mingle Tobey.

Photos courtesy of Instar, Avalon Red.

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57 Responses to “Leo DiCaprio tried to be Tobey Maguire’s wingman at a club, but the girls blanked Tobey”

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  1. Jane says:

    Ha! Either they have no idea who Tobey is or they absolutely do thanks to Molly Bloom’s memoir and either way aren’t prepared to touch him with a barge pole. But I imagine all the members of the Pussy Posse are used to being invisible to women when Leo’s around – when was the last time Lucas Haas got any interest from the gossip columnists?

    • Noki says:

      He always came across as rude and uncharismatic in real life. And in Mollys Game he was portrayed like a real jerk,could also be Leo Dicap being your bff,that may arise insecurities.

      • Nina says:

        I could never even look at him after reading that book! What a terrible person.

      • Ajda Nguyen says:

        He is way more than rude and uncharismatic if Molly Bloom’s memoir is to be believed (and I believe her). He is a downright sociopath who enjoys destroying lives on a whim. So I am glad that he can’t get any.

        Also isn’t Leo over 50 now? I love these writers who shave years off his age. If Tobey is really the same age as Leo, I am happy that he is having no success in drawing young 20-something’s into his web of sociopathy (pun intended).

      • Kay says:

        Contrary to popular belief, Leo has actually been linked to women older than him such as Naomi Campbell, and women older than 25 such as Katie Cleary, Laura Whitmore, and Rihanna. He publicly dates women in their early 20’s but his taste in women is broader than that in real life. That’s why I tend to believe most of his official relationships are PR relationships.

      • KrystinaJ says:

        He’s actually 47.

  2. Lu says:

    There’s something really pathetic to me about being middle aged and still patrolling clubs for young women with your ‘wingman.’ Toby may benefit from investing that energy into therapy and learning how to accept himself in his current stage of life, rather than distract himself with these shallow ego boosts, which aren’t even working anymore. He comes across as emotionally immature.

    • Dena+Landon says:

      Same. I remember being in my 20’s in clubs and bars getting hit on by these much older men and I was always thinking – why aren’t you home with a wife and kids?? What are you doing here?

    • Merricat says:

      I always thought there was a strong homoerotic element.

  3. Jen says:

    “remember Seabiscuit” just gave me what I needed to start my day.

  4. Abby says:

    This is such a funny story and i love your take Kaiser. Who tipped off the press? A waitress? I could see this happening. Personally Tobey is one of my least favorite actors, for no reason. I’m sure he’s a nice guy. It’s personal preference. I feel like he always looks like he’s about to cry. I didn’t like spider-man, I didn’t like Seabiscuit (even though I am a die-hard horse lover, I love Seabiscuit the real horse, and I love the author of the book the movie was based on). I DID really like the Great Gatsby, but he was my least favorite part.

  5. Noki says:

    Eww i remember the p*** posse term,though Leo said it was unfairly given by the media.

  6. Millenial says:

    Is there a reason Tobey’s acting career has sputtered out? He was a pretty decent actor, but his IMDB is a deadzone for the last 10~ years.

    Is he spending all his time on his gambling ring? Did he get blacklisted after the bark like a seal stuff? Living off Jennifer Meyer’s money? I’m so confused.

    • Princess Peach says:

      He’s unprofessional and mean. He almost got fired as Spider-Man and replaced by Jake Gyllenhaal back in the day. His future father in law Ron Meyer was at that time the head of NBC and had to intervene so his daughter’s boyfriend didn’t get fired. So his bad reputation and honestly the fact that at the end of the day he’s just not that special did him in.

      • deering24 says:

        “He almost got fired as Spider-Man and replaced by Jake Gyllenhaal back in the day.”

        Yeeesh. A creep for a creep. No wonder Maguire is most convincing as a burned-out celeb in those car commercials these days.

    • OriginalRose says:

      I remember reading that he got into a huge amount of gambling debt? Wasn’t that scene in ocean’s 11 (where brad is teaching young Hollywood actors to play poker and they’re ridiculously crap at it) based on Tobey?

  7. SusieQ says:

    I’ve always thought Tobey Maguire has a very unsettling energy about him. He gives me the creeps on screen, so I’d probably back away slowly and then run away in real life.

    • Erin says:

      My husband cannot stand him and I used to laugh about it all the time. When he was still making big movies if he found out or saw Tobey was in it, automatic no. I don’t know exactly what it is and he’s not like that with any other actors but he can’t stand watching him or hearing his voice.

      • SusieQ says:

        @Erin, my stepdaughters and I were comparing him to an extraterrestrial wearing human skin for the first time after we saw the Spider-Man movie in December. That’s the best description I have for what his energy reminds me of.

        I’m 36, so I was in the target demographic for most of his big movies back in the day. He is my least favorite thing about his first two Spider-Man movies and Pleasantville, all movies that I love.

    • Gobo says:

      Molly Bloom did not have nice things to say about him. He’s the poker player who thought it would be funny to try to make her get up on a table and bark like a seal who wants a fish to get paid the tip she was due for organising the poker game.

      • Delphine says:

        I just went and read an article about it. My god what an abusive prick. Of course those women weren’t interested. They probably know.

    • Abby says:

      @SusieQ, @Erin I thought I was weird for feeling this way. I just don’t like watching him on screen. He brings down any movie–he’s why I didn’t like those two Spider-Man movies. I’m 37 so I’m right there with you.

      I think the only movie he’s been in that I liked was Gatsby, but he was my least favorite part.

      • SusieQ says:

        @Abby we can all form a club together! He just never seems to be in the same movie the rest of the actors are in because of the unsettling energy.

        I know I felt like a jerk for having such a weird reaction to him because I kept thinking to myself, “People can’t help their voices and how they move.” But years later, after reading about the incidents that @Gobo describes, I didn’t feel so badly, since he sounds entitled and abusive.

      • Erin says:

        This is funny and my husband will definitely appreciate hearing that he’s not the only one. I was pretty apathetic about him myself until all the crap came out about him being a complete douche. It’s just funny to me because my husband doesn’t even “know” actors, ya know. Like he has a hard time naming anyone who isn’t like George Clooney or Meryl Streep. He sure know Tobey though lol.

    • detritus says:

      This right here.
      Tobey ain’t all right.

      Also, wtf wants to be with an aging and passe actor when you first met Leo? It’s doomed to fail.

      • GOBO says:

        I find it hilarious that a man who gets off on humiliating others must have been humiliated by how this night on the pull played out.

    • Lonnietinks says:

      Same! He gives me very angry energy.

    • Korra says:

      It is interesting too because Tobey has been typecasted in regular guy, salt-of-the-earth type of roles for most of his career. I realize actors are supposed to be playing a part and not their real life selves, but let’s not pretend that a lot of actors don’t bring elements of themselves to the screen anyway. Besides being a jerk in real life, I think his career sputtered because of that unsettling energy you mentioned — it becomes noticeable to audiences after awhile and he no longer is believable as a goodhearted underdog.

      • deering24 says:

        Korra–he played a real scumbag in that Clooney thriller The Good German years ago, probably to counteract his Spiderman persona. This was before stories got out about him, and I was surprised at how convincingly hateful he was. Guess he wasn’t acting. 🙃🙃

  8. reef says:

    He showed up to the club in bootcuts and a sweater during SuperBowl weekend where there were rappers, actors, and athletes. I understand why the ladies said no.

    • It Really Is You, Not Me says:

      Trust your instincts. My college roommate back in the early aughts HATED Mel Gibson with a passion and I thought it was so weird because he was beloved at the time and seemed so harmless. Then all the racism and abuse came out.

      She also hated Alex Trebek and, after her record with Mel Gibson, I have been expecting something horrible to come out about Trebek for the last 20 years.

      • BrickyardUte says:

        I completely agree with about about Mel Gibson, but I feel the need to share my friend’s experience with him. She is married to an iconic singer’s first husband and while not famous has been around all the celebrities for the last 15+ years. She is a feminist and as liberal as they come (as am I) and this experience happened pre-racist meltdown, though it’s clear his views were longstanding and inexcusable. She credits Mel with helping her brother getting and staying sober. He mentored him and helped him to attend meetings and kept up communication and support. She was incredibly grateful as this was an act of kindness from him because neither her nor her brother have any pull within the Hollywood community. Mel clearly fell off the wagon but I have read he is sober again and has been so for the last 10+ years.
        Not trying in any way to excuse his behavior, and support the comments about not liking him. Just a “celebrity in real life” story I thought our group might find interesting. And I find Toby and Leo to be no bueno and I am 38 so also in their heyday demo.

      • whatWHAT? says:

        I recall Robert Downey Jr. saying that Mel was also instrumental in helping him, and was just about the only person willing to give him a shot in H’wood after he got clean.

        the problem with these stories is…

        …just like the old saying “a person who is nice to you but isn’t nice to the waiter/waitress is NOT a nice person” I think still holds true. Gibson did a nice thing for your friend’s brother, but he’s still a misogynistic anti-semitic MAGAt.

      • Ange says:

        Mel probably had a vested interest in keeping people sober, what with the Catholicism and all. It’s how he behaves the rest of the time that’s the problem.

  9. CC says:

    What if there was a third person seated at the table in “My Dinner with Andre?” Every so often the film will show a blonde woman looking uncomfortable and trying to get a word into the conversation but being cut off. It’s not until the credits roll that most of the audience realizes that “Blonde Woman” was played by a dozen different actresses – a different one in each shot.

    • PixiePaperdoll says:


      Would watch!

    • Rachel Phelps says:

      A more apt name for their group would be the Douche Crew. Maybe the reason why chicks weren’t into Tobey is because he’s friends with people who think it’s appealing/cool to refer to themselves as the Pposse in the first place? The douche waves wafting off of them are strong.

  10. lanne says:

    The girls probably told both of them to go home and take their medicine. They were up past their bedtime.

  11. Julia K says:

    2 guys pushing 50 out trolling for young girls. Pathetic. No fool like an old fool.

  12. Sue says:

    46 year old divorced dad creeps on 20-somethings at the club.

    That’s a nope.

  13. DiegoInSF says:

    Yuck nasty creeps lol serves Tobey right!

    • Justwastingtime says:

      Leo may end up having a Truman Capote trajectory. Seriously google Truman Capote as a young man..

  14. Marcie says:

    I’ve never cared much for his movies, though I didn’t hate him in spider-man, there were parts where he came off as creepy in the movie (mainly in his interactions with Kirsten Dunst). Anyway, after watching the NY Post documentary on the Don’s Plum film, I’m pretty sure he’s an awful person. He seems to get off on making people do things for his entertainment, he’s just…off. The doc is worth a watch though, it’s on youtube.

  15. Elsa says:

    The reality is they likely do not remember Seabiscuit – I just checked and it came out 19 years ago! And everything else he is known for – Spiderman, Cider House Rules, Pleasantville is older than that. His last major role was in the Great Gatsby and that was nine years ago!

  16. MelOn says:

    Never thought either of these guys were physically attractive and their behavior makes them even less so. Who needs to date a horrible jerk just because their famous?

  17. Digital Unicorn says:

    Never ever got his appeal – he was/is a decent enough actor who, as others say, ruined his career through bad behaviour.

    The sleaze oozes out of him and the rest of the posse – the same goes for Leo. Leo is a v talented actor but the sleazy is strong with him. You know what they say about judging someone by the company they keep.

  18. Bobbie says:

    I’m surprised the women didn’t hit on Leo.

    • Julia K says:

      Leo is not aging well. He just doesn’t have ” it” anymore.

      • Bobbie says:

        He’s famous and wealthy. That is all it takes for some women. And a lot of women find him hot. There are probably women throwing themselves at him. He doesn’t’ even need game.

    • J says:

      Really? I’m not. He’s a fine enough looking dude but he is older and looks like many of their dads I’d assume. And he’s also known for a young lady penchant so it is probably off putting knowing you’re with someone who fetishizes you.

  19. AnneL says:

    Ugh, I didn’t know he was a creep. It’s not like I’m a mega fan or anything but he always seemed OK to me. I liked him in Cider House Rules. That’s disappointing.

    I just read somewhere else that Olivia Jade was at that party. She’s back. The scandal didn’t sink her.

  20. jferber says:

    I’ve always understood that the two are together. I believe one of their mothers once said so.

  21. Bread and Circuses says:

    I honestly thought both these guys were in their fifties already.