If Leonardo DiCaprio stays unmarried & childless for 11 months, he wins $500K?


Jonah Hill stared into the face of the man he called a friend. Jonah felt his chest tighten with longing, desire, fear. “Is this love?” he asked himself. “Is this wrong? If it’s wrong, why does he feel so right?” Oblivious to the flashing lights, oblivious to the cacophony of shutters, screaming voices and the WHOOSH of heat and emotion coursing through his body, Jonah continued to stare up at Leonardo. “If he looks at me by the time I count to ten, then I’ll know he feels the same way,” Jonah told himself. “One… two… three…”

These are photos from the Wolf of Wall Street premiere in NYC a few nights ago. Obviously, this was the happiest day of Jonah Hill’s life, coming just ahead of the time Brad Pitt and Angelina Jolie came to his birthday party. Believe it or not, this post is not about Jonah though. I meant to write about Leo! I don’t know what’s going on with Leo these days. Is he still with Toni Garrn? Did he try to hook up with a newly single Miranda Kerr? Or is Jonah Hill all that Leo needs these days? Well, the Enquirer claims that two of Leo’s closest friends are just 11 months away from ponying up $500,000 to Leo after his “no-commitments, bro” modelizing ways have meant that he’s not a husband and father by the age of 40.

Leonardo DiCaprio’s two best buds – notorious gamblers Tobey Maguire and Ben Affleck – are suddenly sweating because Lea’s thisclose to collecting $500,000 on a bet they made years ago.

Said one pal: “Tobey and Ben, both high-rolling gamblers, bet Leo $250,000 each that he’d be married and a dad by the age of 40. Leo took the bet and went on to date a string of supermodels (Gisele, Bar, Erin) but never got serious enough to tie the knot. Now, with his 40th just 11 months away, Tobey and Ben are sweating big-time about coughing up a staggering quarter of a million bucks each!”

[From The Enquirer, print edition]

“Do you love them more than me?!” Jonah sobbed to Leo. “Why would you make that bet with THEM and not me?!”

Anyway, is this a thing? I could see it being a bet amongst Leo’s friends, but would they bet THIS much? I would think a gentleman’s bet of $10,000 would do the trick because, seriously, who needs to spend $250,000 betting on Leo’s crotch? Also – what kind of idiot looked at Leonardo ten years ago and thought, “Oh, he’ll settle down eventually”? NO ONE. No one thought that. Leo will always be Leo. He’ll always be this way.

What happens if Leo marries Jonah? Will Ben and Tobey still have to pay up?



Photos courtesy of WENN.

You can follow any responses to this entry through the RSS 2.0 feed.

74 Responses to “If Leonardo DiCaprio stays unmarried & childless for 11 months, he wins $500K?”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. Amelia says:

    Bloody hell, Jonah, calm down dude.

  2. Audrey says:

    They’re idiots if they bet that much

    I don’t think Leo will make them pay though

  3. karolina says:

    I don’t believe it. Aren’t both Toby and Ben married with children? The money would be better invested in their children’s future. So dumb if this is true.

  4. Neffie says:

    HAHAHAHA Jonah looks like some crazy fan that managed to snag a picture. stop embarrassing yourself bro!

    • Mary says:

      Ha! I was just thinking who knew Jonah was Leo’s biggest fangirl!?

    • Moiselle says:

      Jonah looks like a starf***er. Or like the nerd kid that finally got to sit at the cool kids table.

      • Virgilia Coriolanus says:

        Exactly that–but he’s a douche too. I read on his last post that he trashed the JP’s New Orleans home (had a party and left it), so that’s why they weren’t friends anymore. So I always think of him as an ass kisser of the highest order—except one day you’re going to show your true colors. You can’t keep that up forever–but I do think he puts on his nice face for people he thinks can help him out, give him a leg up in the business. But acts like an ass to reporters, to the ‘little people’ i.e. non famous. Someone also posted this story about how she saw him in a resturant w/a group of friends—he wanted everyone to know who he was, but didn’t want anyone coming up to him, trashed the table and didn’t tip (and I think she said he wanted free food too). Dick.

      • lisa2 says:

        @Virgilia not sure if that story is true about Brad/Angie being mad at Jonah. He was at the Oscar Ceremony when Angie got her Humanitarian award. There is a picture of Brad and Jonah smiling and laughing together. Not looking mad at each other at all.

        I really liked Jonah during the promotion of Moneyball. I haven’t been following him much after that.

      • Virgilia Coriolanus says:

        I’m not entirely positive it’s true–it’s just what I read on a previous post from someone else—but I still see him as an ass kisser of the highest order.

  5. FingerBinger says:

    I think Jonah might be in love. Look at how he’s looking at Leo. Anyway, the story sounds true. Those guys would bet on anything.

  6. Birdie says:

    It’s my birthday today, so I’ll be not a bitter b*tch today and say: Good for you, Jonah. Enjoy being next to Leo, I would look even more like a happy puppy.

  7. Eva says:

    George clooney has a bet like this with Michelle Pfeiffer and Nicole Kidman.

  8. Penny says:

    Every single photo of Jonah at this premiere is comedy gold.

  9. Marianne says:

    What if he got married, but didnt have a kid? Or what if he got someone pregnant, but they didnt get married? Is it like a package deal for him to get the money?

  10. break says:

    This film is the most misogynist piece of “art” I’ve seen in years. It’s just incredibly exploitative and gratuitous. I suspect that it perfectly represents Leo’s attitude toward women.

  11. j.eyre says:

    That’s it, I need better friends. The most any of the losers I know bet me was that I couldn’t eat an entire tub of Chewy Gooey Chocolate Ice Cream after my last break up. MY pay off was to be allowed to choose the rom com that night AND to clean up the bathroom floor after I threw up the ice cream.

    • Aysla says:

      Awww. Have you been able to eat that ice cream flavor since? I hope the rom com you chose was worth it, at least! ;) My friends bet me a measly five bucks to eat the hottest pepper in the world (I believe it’s called the Moruga Scorpion pepper), and I stupidly took up the challenge… even though I’m a horrible wimp when it comes to spicy food. I felt really really unwell, jittery and shaky, my heart was thudding, my mouth and face were on fire, and then I spent all night throwing up. On the bright side, I discovered that while milk does absolutely nothing to temper the heat… continuously sucking on ice cubes does.

  12. jinni says:

    If Leo married Jonah, Lucas Haas would go berzerk. Full blown Left Eye burning down the house/ Waiting to Exhale rage. He didn’t take all of those bike rides with Leo and his piece of the moment, give up his career to follow Leo around the world, and not settle down like most of Leo’s other friends just to be tossed aside. Everyone knows he’s been Leo’s long suffering homie lover friend. Jonah better just be happy being a side dude because Lucas is will always be the main dude. J/K

  13. V says:

    Anyone else hearing the song Hungry Eyes in their head when they look at these photos?

  14. Virgilia Coriolanus says:

    I would love it, if Leo dated a non blonde, non model woman, who he eventually married and made little Leos with–but I ain’t holding my breath. He’s a free wheeling, modelizing mama’s boy–and he ain’t ever gonna change until the entire catalog of VS says no to him. Which ain’t happening. But damn, Leo–at least pick a non VS model to switch things up.

  15. Littlewood says:

    Poor Jonah, wait till he hears that Leo has been seen out partying with Orlando at least 4 times this past week or so. I want them to be a couple just to see the media explosion if Bloom shows up as Leo’s date at the Oscar and not Miranda, lol. I’m naming them Leolando from now on.

  16. Barbara says:

    My gorgeous relative parties at the same places as Leo. I wonder if he knows she and her friends kinda call him an old man.

  17. Pink says:

    1 – Looking good, Leo.

    2 – Can’t wait for WOWS!!!

    3 – I can’t blame Jonah, I would do worse lol.

    4 – Enquirer, eh?

    That’s all!

  18. Maritza says:

    I believe Leonardo Dicaprio will be an eternal bachelor like Keanu Reeves. At least Leo seems to be having more fun than sad Keanu.

  19. J says:

    I snort-laughed at Kaiser’s verbal depiction of Jonah’s love for Leo. I mean, look at that guy, he just wants to inhale Leo and NEVER EXHALE for the rest of his life. Does he want to be him or be with him? He’s probably not quite sure either.

  20. Trixie says:

    Hahahaha This set of photos is killing me. My stomach hurts from laughing so hard. Jonah, settle down little dude. omg

  21. Anna-fo-Fanna says:

    These photos are Jonah’s “baby Bieber” photos from NOW ON. Please, you have to post these with every Jonah Hill story from now to eternity!

  22. Nessa says:

    Just wanted to leave a comment because bahahahaaaa these pictures of Jonah are hilarious. Jesus, guy… Bring it down!!!!

  23. Megan says:

    Jonah hill is so far up the ass of celebrities more famous than him I’m constantly wondering how he is able to breath.

    I really don’t like him. He gives off a major aura of douchiness.

  24. Murphy says:

    Just look at him, he turns more and more into Jack Nicholson with every passing day

  25. Skye says:

    If he manages not to marry and divorce in the next 11 months, he’ll have saved many times that, bet be damned.