Leonardo DiCaprio & Cameron Diaz: old friends or friends with benefits?

Leonardo DiCaprio has been single for more than a month. Or so. I don’t really think Leo is all that different when he has an “official” girlfriend and when he doesn’t, so no 20-something model is ever going to be safe when Leo is around. Since breaking up with Erin Heatherton, there’s only been one girl loosely associated with Leo – his Wolf of Wall Street costar Margot Robbie. She’s blonde, she’s “22” (cough) and she’s very pretty, with that sort of haughty look that some men love. The complaint against Robbie is that she’s an actress… and Leo doesn’t DO actresses, generally speaking. But what if he’s in the mood to go completely against type? What if he’s in the mood for a quick hookup with some blonde, with a great body, an actress… who is 40 years old? SHOCK! Page Six claims that there might be something brewing with Leo and his friend Cameron Diaz:

The party continues for single Leonardo DiCaprio. The “Django Unchained” star and Cameron Diaz hooked up, as pals, at the opening of hot new club Rosewood on Friday.

“Miranda Kerr and a group of girlfriends were the first to show,” said a spy at the cocktail lounge, adding that models Jessica Gomes and Jessica Hart were close behind. Later, “the crowds parted when Leo entered” and he sat with Kerr and company.

“He was texting until Cameron arrived,” a source said, “and it was obvious they are great friends . . . he was very excited when she came to meet him, and he got up from his table to guide her to where he was sitting.”

The models then did what models do: danced on banquettes, in this case to the tunes of DJ Regg Ruck, and drank Champagne and Belvedere. At 3 a.m., DiCaprio made sure to “tip the waitresses and say thank you” before he and his posse headed out. Leo was spotted the next day at a raucous Day & Night brunch (where one loaded reveler stuffed $2,000 in singles into a fog machine).

Diaz was seen dining at The Lion with a pal.

[From Page Six]

Yeah, it doesn’t say they hooked up, only that Leo looked very happy when he saw her and that he seemed attentive to her. Considering Camy’s dating history and Leo’s dating history, I think Cameron is probably into it and Leo is probably just hoping for a quick hookup. He wants to maintain their friendship, but he likes her and he likes her vibe. They’ve been friends for more than a decade, after all. He’s never going to get serious about Cameron or anything, but he’s probably up for a friends-with-benefits thing. And Cameron… well, I think the girl is a mess, but whatever.

Photos courtesy of Fame/Flynet and WENN.

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20 Responses to “Leonardo DiCaprio & Cameron Diaz: old friends or friends with benefits?”

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  1. Little Darling says:

    Meh. The star power of these two shines out nothing dazzling. If they bump uglies more power to them. It’s apparent they are both hot messes when it comes to dating, so doesn’t that kind of wipe out any potential of this being exciting?

  2. Ms Kay says:

    Uh… Leo doesn’t get past the 25+ years old expiration date (and I think I’m being way generous here) vagina and brainy wise, so let alone Jurassic old…

  3. Erinn says:

    Her face is looking way better… must be the makeup? She was looking haggard for a while there, around the ‘bad teacher’ time. Or maybe it’s because I don’t see her in motion.

    Either way she’s waaaaay too old for Leo.

    Not that Margot looks 22 in my opinion though. She looks like 26 or so… I’m 22, and she doesn’t look like any of the girls my age that I’ve come in contact with.

  4. KellyinSeattle says:

    The title caused me to have unpleasant pictures in my mind!!
    Leo was good in some movies, but he usually reminds me of a kid playing make believe. The baby face doesn’t bode well in Hollywood, nor in my “sexy vibes” file.
    As for a relationship between them, I doubt many people care.

  5. Miss Kiki says:

    I wonder if Cammy is still banging P Diddy? That was all kinds of gross and to be honest I find Leo almost equally as icky.

  6. stellalovejoydiver says:

    If Leo didn´t have that specific type, I´d say it is more likely that him and Miranda Kerr are having an affair while Orlando is still in South Africa.

  7. Nessa says:

    I think Leo and Cammy already hit it and quit it a while ago. I’m sure he’d be up for it again on a very casual level. He very well could be hitting Miranda discreetly, too. This is Leo we are talking about.

  8. emem says:

    cameron diaz is one actress i mostly consider lucky to be in the spotlight and rich too as an actress. she’s never been prety @ all to me. @ least some of d actresses may not be facially beautiful but their body makes u like them but she nothing @ all. put her in d middle of kim kardashian, jennifer lopez, beyonce one forget she’s a woman

  9. hoya_chick says:

    Uh….well he DID Blake Lively. Or are we not counting her as an actress? LOL.

  10. truthful says:

    Hollyweird just swaps germs all the time. yeech!

    I’m beginning to think its a prerequiste to have slept w/a infested A list celeb and then its a free for all.

    Diddy, A Rod, Justin
    (rocks back and forth)

  11. aston martin says:

    Cameron has those husky dog eyes that will never truly age. Guys barely notice crow’s feet when they surround eyes that amazing.

    Leo… Leo, Leo, Leo. I love him. He is just EPIC as an actor. He’s our generation’s Pacino/DeNiro/Daniel Day-Lewis/Jack Nicholson/whoever else was epic a generation ago. He’s just GOT IT. He’s THE MAN. He doesn’t do press, he only does the occasional charity appearance, and still he seems omnipresent. He’s kind like God in Hollywood… unseen yet everywhere, and powerful enough to part the sea. WHOOPS, I mean the crowd. I don’t care one bit who is or is not banging.