Us & Star: Rihanna & Leo have hooked up for years, ‘he’s the best she ever had’

Rihanna

Rihanna and Leonardo DiCaprio both partied on P. Diddy’s yacht in St. Barts over the holidays. When they got back to Los Angeles, they attended the same Playboy mansion party. There were conflicting reports, but some spies say Leo and RiRi made out and left the party together. God knows Rihanna has bad enough taste in men to make this story plausible. I’d love to see Rihanna put Leo through the wringer. His reputation with women deserves some table turning.

This week’s issues of Us Weekly and Star have some details about the alleged hookup. Both outlets say this isn’t the first time. I’ll start with Us, picking up with the “hookup history” between these two:

DiCaprio had his eye on Rihanna s far back as May 2009. During a night out with friends at L.A. club Villa, he stared at the beauty “for an hour,” says an eyewitness, even asking the DJ to move his equipment out of the way so as not to obstruct his view. They flirted again at the Coachella music festival in 2011. By then, they were “party friends,” shares an insider. “They’ve rocked in the same room a lot.” Notes the friend: “Leo’s had her to his house for get-togethers.”

To ring in 2015, they brought the fun to the beaches of sunny St. Bart’s. Using their respective crews as cover, they hung together all week. “Rihanna is sexy, and they have a connectin,” says a DiCaprio source. “She’s the kind of girl to keep you on your toes — smart and a little unpredictable.”

“Neither one is looking to make this anything more than fun,” explains a source. “He’s into her, and they’re enjoying it.” Two free spirits, they are not the types to commit. DiCaprio, off to shoot The Revenant in Atlanta in February, has blamed his work schedule for his long list of failed affairs. And Rihanna, says a source, dumped ex Drake when he started taking aobut buying a ring. “This,” says the insider, “is a no strings kind of deal.”

[From Us Weekly, print edition, February 2, 2015]

As gross as this sounds, I don’t have trouble believing that Rih and Leo habitually hook up when they’re both single. It’s probably a power thing for both of them. What I don’t believe is that Leo is amazing in bed, but that’s what Star is saying: “Their chemistry is off the charts. Rihanna loves Leo’s attitude about life, and he thinks her laid-back demeanor is irresistably sexy. She says he’s the best she ever had.” Girl, no.

Leonardo DiCaprio

Rihanna

Photos courtesy of Fame/Flynet & WENN

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

100 Responses to “Us & Star: Rihanna & Leo have hooked up for years, ‘he’s the best she ever had’”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. tifzlan says:

    More like SHE’S the best HE’S ever had.

    • Maria says:

      Agree 1000000%

    • Sunny says:

      I have read blind items that suggest RiRi is amazing in bed. That I can totally see. But this story feels made up because I cannot picture Leo being good in bed. It has nothing to do with how his looks have changed or even his terrible beard and everything to do with the fact that I think he is immature, selfish, and an egomaniac.

      Can you imagine how often you would have to tell Leo how much you loved his dick? God, he totally strikes me as the guy who needs you to tell him how good he is in bed. All without the curtsey of making sure you finish as well.

      Uhhh yuck, Leo.

      • Wren33 says:

        Of course you never know, but he just seems selfish and not terribly sensual. Given the fact that he dates a series of very similar blond models, the women scream “trophy” more than someone he is totally into. Here ends my snap judgment.

      • MaiGirl says:

        In her memoirs, Bobbi Brown (former model and wife of Janie Lane, the late Warrant lead singer) wrote about the fact that he was pretty terrible and she basically did all of the work, and she wound up either leaving early or kicking him out, don’t remember. While it was a long time ago, and he may have gotten better, his entitlement in bed mirrored his entitlement in life.

      • lukie says:

        I am convinced RiRi ties him up and makes him her B*tch.

      • The Original Mia says:

        All of this. There’s no way he isn’t a selfish lover.

      • FLORC says:

        Wasn’t it said Leo only last about 2 minutes? That he’s kind of just there for himself? Anyone remember this?

    • Jan Harf says:

      Exactly.

      • Sam says:

        If anything probably the opposite … Last month Rihanna’s interview in Vogue or one of those mags….she was quoted as saying what she finds sexy is when’s man tells her what to do.

        And anyone who lets a guy beat on her isn’t what you are guys delusionallay posting here , it wasn’t as that was the first time Chris Brown knocked her around, she didn’t even leave him until the media pressure forced her to and she was desperate enough that she went back to him and it was he who dumbed her the second time.

      • HH says:

        @Sam – “Let’s a guy beat on her…” >>> Domestic violence is not that simple. It is very traumatizing psychologically. Also, I don’t believe the public and media shamed her into breaking up with him. I think it gave her the mirror that most people don’t have, and she got a chance to ask herself, “WTH am I doing?”

    • huh! says:

      LOL! What a joke.

    • Mispronounced Name Dropper says:

      Ha. Take that Chris Brown!

  2. Milena says:

    Although it would be nice to see Leo go after a lady for more than just her looks, he’s turned into such a skank! And that beard makes him look like a scraggly hill dweller – not sure who would consider him a catch these days. RiRi should hit it and quit it. Fast.

    • huh! says:

      And the lady would be Rihanna? LMAO
      Leo’s stabdards were never high but he hit an all time low with Rihanna.

  3. paola says:

    Leo dating a non blonde? IMPOSSIBLE!

    • Tiffany says:

      There have been blinds about Leo having an attraction to women of color but will never go public with the relationship (Giselle was the exception). I believe this one.

      • tifzlan says:

        Wtf? Are we back in 1945 now? Why would you not want to go public with a relationship?

      • Bridget says:

        Gisele may be Brazilian, but she’s got a very European heritage and I don’t really think anyone would describe her as a woman of color. It’s no coincidence that she was discovered as a model – scouts targeted the region she lived in based off of European immigration and settlement patterns.

      • How is Giselle the exception?!

      • AG-UK says:

        @Bridget
        During World Cup they had a week of shows on BBC about Brazil and where she is from 90 are German background and the older generation do not speak Portugues. They all look similar to her, only recently they have tried to get models from Brazil that actually look like 90% of the population.. not sure if that’s correct but def. the blondes in minority. And him with the beard, where is my banjo..

      • Branvoyage says:

        Giselle is a woman of color?

      • Bridget says:

        AG-UK: Yep. The Brazilian model “boom” that came with Giselle was actually because scouts were exploiting the immigration pattern, and got these tall, tan and lovely women with a slight exotic flair but traditional European features.

      • Moneypenny says:

        Brazilians, like Americans, come in all races. Giselle is a white Brazilian. She is not a woman of color.

      • Vvvoid says:

        How is Gisele a woman of color, realistically? Her ethnicity is irrelevant, as is mine, when the average person would look at her and treat her as a white woman. I’m substantially Native American, which is classified as non-Caucasian/Mongolid, but my experience is that of a white woman. Just saying.

    • perplexed says:

      Yeah, I think that’s what surprised me more than anything else. Also how tall is she? I thought he only went for 6 footers.

    • sally says:

      I don’t think Leo dates or sleeps with women of color. I don’t believe this story at all.

      • FingerBinger says:

        He has dated women of color. I’m pretty sure I heard something about him briefly dating Naomi Campbell a few years ago.

      • Asher says:

        Why not? Would that offend you, Sally?

      • sally says:

        Well, i’m asian so it would not offend me. i don’t believe it because he’s never linked to or seriously dated a WOC. even on his birthday the bevy of models didn’t include any non-whites.

      • jinni says:

        He went out with Kidada Jones (Quincey Jones’s daughter) back in the 90’s.

  4. AbbySaurusVex says:

    hahahahahahahhahaha
    No.
    Leo looks like Grizzly Adams got drunk and hooked up with the pillsbury dough boy. Gets lonely out there in the mountains.

    • Jem says:

      Does the Pillsbury Dough Boy say “tee hee hee hee” whenever Grizzly pokes him…?

    • Hudson Girl says:

      Um. You just reminded me that when I was little- in elementary school- I used to have a crush on Grizzly Adams. So, thanks for giving me a dose of inner turmoil.
      (I suppose this explains my previously unexplained Lumberjack Chic weakness in men.)

    • lamamu says:

      Oh, thank you for the laugh! I can finally get on with my day in a great mood. Cheers!

    • JenniferJustice says:

      How dare you put down Grizzly Adams. He would be so offended.

  5. kls2686 says:

    The his/hers photo comparison is astounding – Beauty and the Beast!

    Girl, you can do WAY better than this douche.

  6. Jem says:

    Maybe she just has low standards in bed.

    • AbbySaurusVex says:

      Maybe it was a dare. Her and Katy Perry are daring each other to sleep with mangy people.

      “Leo DiCaprio!!! Double Dog Dare you!!!!

    • bns says:

      How do you know how he is in bed?

      • perplexed says:

        Obviously, I wouldn’t know, but didn’t some model write a book where he mentioned how he was? I can’t remember if she said he was good or bad, but think she might have complimented him. And I cannot believe I am typing this out…

      • Maria says:

        so because someone wrote it in a book its true?

      • perplexed says:

        “so because someone wrote it in a book its true?”

        I don’t know. I was just contributing to the conversation.

    • Zwella Ingrid says:

      Its hard to believe that Leo could be better in bed than Drake.

  7. Amy says:

    You know what…I’m going to say it. Rihanna is imo the, to one of the, prettiest celebs in the celeb scene. Even without makeup she’s got amazing bone structure and her nose is so adorable.

    All that being said the inside of her head must look like a unplugged ice cream freezer left out to rot in the sun. She has the worst taste in men and prioritizes the physical (which isn’t wrong in itself) over just getting a quality dude.

    Is it impossible to find quality dudes who want to hook-up? Maybe. But damn such a gorgeous girl letting that beard hit it, ugh.

  8. Mandy says:

    Well, he’s certainly been with enough women to have a lot of practice….

  9. scout says:

    ANYBODY who is “normal/regular” is the best thing ever for her after what Chris Brown did to her in the past, I am sure. Good luck to ya.

  10. amanda says:

    they both seem like they think they’re great in bed because of their looks or reputation, but really, nobody wants to say anything to them, but they’re both terribly average and selfish in bed.

    lol.

  11. Chris says:

    OMG! You can do much better Ri Ri. Who is feeding this gossip by the way. Ri Ri people?

    • Ankhel says:

      Yup. Ri Ri’s people. As in, “Leonardo f***ing DiCaprio’s so much better than you, Chris! Chriiiis?”

  12. Eleonor says:

    I tend to think they are more party-friends with benefits.
    And honestly I think Rihanna is faaar way hotter than all the VS models he has been dating lately.
    And she has awful taste in men.

  13. ab says:

    ugh, leo is so gross these days. physically and behaviorally. ’90s teenage me would never believe that leonardo dicaprio was capable of becoming so completely unattractive.

    I kind of get the rihanna/leo hook-up since they’re both wild partiers, but I’m not sure anyone can make me believe he’s the best she’s ever had.

  14. Loopy says:

    He looks like a lazy selfish sloppy lay.

  15. Bridget says:

    I’m pretty sure that the only person that thinks Leonardo DiCaprio is the ‘best they’ve ever had’ is Leonardo DiCaprio.

  16. **sighs** says:

    Hahahahahahahahahahah.

    Thanks for the laughs, bed head.

  17. Cindy says:

    Karma for Leo, I think, would be to fall in love and have his heart trampled. I don’t think it would be Rihanna because she’s not his type. How is it this guy hasn’t ever been rejected, even once? Nothing touches him.

    • qwerty says:

      Blake Lively dumped him and one of his co-stars said he spent the whole day in his trailer or something.

      • Jegede says:

        @qwerty – Yup. It was on of Baz Lurhman’s assistant who accidentally outed the fact that Leo refused to come out of his trailer post break-up, and his behaviour from then on became intolerable for a few crew members.

  18. sara says:

    Leo is really gross. He is quickly turning into version of Marlon Brando and that isn’t pretty.

  19. TeresaMaria says:

    Leo is channeling Benicio Del Toro on that top picture.
    I mean, current Benicio Del Toro, not the hottie he was 10 years back

  20. bns says:

    He’s old, but this doesn’t bother me. She’s the most beautiful celebrity in the game right now, and she deserves to have some fun in her love life. Get it.

  21. perplexed says:

    Weirdly, I think Leo might be better than some of the other guys she’s gone out with. He doesn’t have a reputation for beating women (i.e Chris Brown) and he doesn’t kiss and tell (sometimes Drake seems to be doing that?

    • Maria says:

      what you say is true but its really not the way someone should look at finding a partner. “oh he doesnt beat me until im almost dead”

      • perplexed says:

        True. I wasn’t trying to convey that I think Leo is a great catch in the context of larger mankind, and I wouldn’t say Leo is an ideal mate for anyone, but in the context of who else she has dated, he strangely seems to come out on top.

  22. Nessa says:

    I honestly think this a ‘notch in the belt’ type of thing for both of them. It boosts their egos to add such a high profile name to their lists of conquests.

    Either way, it makes me feel icky to think about it! Blaaahhhh.

    • Maria says:

      i dont know about rihanna but how is having been with Leo a great thing? its hardly an exclusive club. its like saying “i ate at McDonalds” no one is going to think you are something special.

      • Liv says:

        Your comment is cracking me up! True! He’s nonetheless still a big name and I can see her being fascinated by it. And vice versa of course.

      • Jegede says:

        @Maria – Exactly being with Leo is not even a career maker for non descript models any longer.

  23. Maria says:

    “She says he’s the best she ever had.” ”

    that could very well be true and would be very sad.

  24. Lucy says:

    Good Lord(e). I am not the only one who thinks she could do WAY better, am I?

  25. JenniferJustice says:

    I can see them being party buddies – even friends with benefits, but I can’t accept that he’s the best she’s ever had. No way.

  26. anne_000 says:

    “She says he’s the best she ever had.”

    I seriously doubt that’s what she really thinks. Whoever told STAR this must be from Leo’s camp.

    I know Leo is a player, but I don’t think of him as some kind of ‘Sex Genius.’

    • Seriously serious says:

      Who profits from such gossip? It certainly makes clear that the audience shouldn’t consider Rihanna and Leo to have a serious relationship. It suggests that it ain’t much worth hunting them or expecting to see them together and to photograph them together.

  27. Branvoyage says:

    Leo is a Scorpio, they are supposed to be amazingly passionate in the sack. Js

  28. minx says:

    Hooking up? I believe that.
    If he’s the best she’s ever had, eew.

  29. Jenny says:

    I highly doubt Leo is good in bed. He probably just lays there like a whale expecting the other person to do everything.

    • Seriously serious says:

      He is a smoker … Rumour has it they don’t last. πŸ˜€ πŸ˜€
      On the other hand there are these little blue pills … πŸ˜‰ πŸ˜‰

  30. Mispronounced Name Dropper says:

    As a big fan of Leo’s work ( I like some of his movies too) it warms my heart to hear that he and the lovely Rihanna (she is everything) have been making love on a regular basis, because I was beginning to worry, just a tad, about what seemed like an endless procession of white chicks for my man Leo. Anyway, keep up the good work, Leo, it’s a tough job but someone’s gotta do it.

  31. M says:

    I still just see the young kid from Growing Pains……

  32. Newgirl says:

    I really don’t get the love for Rihanna and the hate for Leonardo dicaprio for this pairing. I admit her music is catchy. If comments are saying that she can do whatever she wants then so can Leonardo.. He is gross… But isn’t she kind of gross for getting with him then?

    That’s all I got.

    • perplexed says:

      I think her music videos are kind of gross, so, yeah, I’m a little surprised she’d be considered too good for him. Is it because of her youth? She’s very pretty, but nothing about her actual image and presentation really screams that she’s looking for someone outside of Leo’s type (which seems to be most of single Hollywood, I think?). If she suddenly got interested in…uh…maybe Benedict Cumberbatch (and his somewhat weird eyes), I guess that would shock me.

  33. Barbara says:

    I say this is a media driven relationship…..and BS in truth

  34. Vvvoid says:

    Sigh. Rihanna is the sexiest thing I’ve ever seen in my life. Leo would be lucky, but it would surprise me if he could appreciate or know what to do with that body having seen the gangly man-bodies he typically prizes.