Celebrity gossip like this — the kind that comes from “sources” who overhear something at a restaurant or someplace — is ridiculous and not really something I spend a lot of time looking at, personally, (if you can believe it!), because 9.5 times out of 10 it seems false and invasive and boring. But then there is that .5th time where it’s just, like, so on the nose and sounds so much like how humans act and talk that you feel as if you are IN that restaurant with Leonardo DiCaprio, Kevin Connolly, and those twelve women!!! From Starcrush:

Leonardo DiCaprio recently had dinner in New York with his friend/fellow actor Kevin Connolly and 12 women (because 13 would’ve just been silly) [Ed. Note: Perfect. Perfect perfect perfect.] and allegedly spent the entire time bragging about how everyone else is just dying to spend a day in his shoes.

According to an eavesdropper who was supposedly sitting next to the group, “Leo talked about the fact that he is sleeping with ‘multiple women’ right now. He was totally open about it. Kevin looked at Leo and told him, ‘I want to be you.’”

“Leo replied, ‘Everyone does,’” the snitch said. “He was acting very nice, but is very arrogant.”

After promising to take Connolly on vacation someday (just ask Jonah Hill what that’s like), Leo footed the entire bill and took everyone clubbing before heading back to a room he’d booked at the Trump hotel.

Surrounded by 12 women and Kevin Connoly, Leonardo DiCaprio, speaking to no one and everyone, declares, “I’m sleeping with multiple women.” Kevin turns to him and says, quietly, reverently, “I want to be you.” Leo: “Everyone does. I promise to take you on vacation someday.” The 12 women clink their forks to their full plates without speaking. Kevin Connolly’s eyes widen at the prospect of being taken on vacation. “Me?” he thinks to himself, “A member of the pussy posse?” Leo’s steely blue eyes lock with Kevin’s as if to say, “Don’t get ahead of yourself, Kevin. I take lots of men on vacation.” Still, Kevin remains lost in the idea until he looks up and realizes the 12 women and Leo were gone. Was it all a dream, he wonders? Were the 12 women meant to be the 12 apostles, and was Leo meant to be Jesus? Do I have to pay, or…?

Comments (35)
  1. I read the headline as “Kelly Conaboy Is So Jealous Of Leonardo DiCaprio, Oh My God, You Have No Idea.”

  2. It’s times like this that I am so sad that “You Can Make It Up” seems to be retired.

  3. Does anyone else ever think that it must just be so dreadfully dull to be one of the bevy of anonymous ladies? I hope they brought books or traveling chess or something. Unless they’re not allowed to have personalities. Then I hope they are robots. SEXY robots.

    • but they get to maybe sleep with Leonardo DiCaprio, who is famous and rich and handsome!

      i’d be p stoked if i was them

    • You’re so smart, lbt! I bet they are bored but that they do that on purpose to look bored and cool like fashion models. Also do you think they’re all best friends or is it just like a constant episode of The Bachelor? Maybe they are all in a book club or something.

      • I like to think they are all besties who made Leo hang with all of them, because as the Spice Girls said, if you wanna be my lover you gotta get with my friends. And they happen to have eleven best friends. So deal with it, DiCaprio.

        Because lets face it, if he’s sleeping with all of them, I have to imagine that there is a schedule and they are, at best, smanging every other day. That is like 47.5 hours of downtime! Yes, there is sleeping, but that’d only eat like 20 hours. I hope there is a raquetteball court or painting lessons, because otherwise I don’t care how rich and handsome and famous Leo DiCaprio is, that’d be so boring.

        • Going out to dinner with Leonardo DiCaprio probably isn’t THAT boring. I mean, he probably has some cool stories that don’t involve his man vacations.

          Plus, isn’t he best friends with Kate Winslet? I definitely don’t want to hang out with the guy from Entourage, but some of his friends are probably cool.

        • Oh yeah, of course the Spice Girls got it right! Then it’s probably not so boring…I’d love to hang out with my 11 best friends all the time even if they were all sleeping with the same dude. (But not Mr. Truck…if my 11 best friends were all sleeping with Mr. Truck I’d have to start cutting people)

      • I’m really enjoying the idea of the Leo’s Ladies Book Club, where they read things like Ulysses and The Brothers Karamazov in the original Russian, and then sigh and regretfully mark their places, remove their glasses, change into super high and uncomfortable shoes and shake out their ponytails when Leo says they’re on.

  4. Chin up, Kevin. You don’t have to be a Leonardo DiCaprio-grade-asshole to sleep with multiple women. Lots of regular-grade assholes do it every single day.

  5. That Eavesdropper is really putting in his work to try to get that promotion to Spy.

  6. In all seriousness, thirteen WOULD have been silly, and a bit unfair. I mean, there were two guys and twelve women, and really, no one likes to be the 8th wheel.

  7. “I tell you what. I’ll do you one better, Kev,” our source heard Leo say after signing off on the check. “You see. I make it a policy to sleep with everyone I take to dinner.” Leo then reportedly locked eyes with Kevin and repeated “Everyone.”

  8. This is some seriously amazing Kevin Connolly/Leo DiCaprio fanfic.

  9. I love the pic used for the post!

    “You like that Kevin? I call her #8. Her real name was Betty but you have to forfeit your name to sleep with a member of the Pus…err, Best Friends Club. You like that huh? You like #15…er, Kevin??”

  10. Serious question: Am I supposed to know who Kevin Connolly is?

  11. Leonardo DiCatchaho, get a life already. Just so immature and embarrassing!

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