This story may or may not be true. I’m betting that it’s completely fake because Rihanna can do better than a dude who plucks his girlfriends out of the Victoria’s Secret catalog. Then again, Rihanna doesn’t have the best taste in men at all. And Leo’s on the rebound, sort of. He broke up with Toni Garn late last year and spent his holidays in St. Barts, on the beach and surrounded by models. Likewise, Rihanna partied in St. Barts for New Year’s Eve at P. Diddy’s yacht party. Maybe they crossed paths, who knows. I don’t want to think about it.
Bad news: Thinking about “it” isn’t optional because TMZ says Leo and RiRi were both back in Los Angeles this weekend. Some eyewitnesses say they hooked up at the Playboy mansion. One of Leo’s posse members denied anything happened, but others are all like, “Yaaaasssss.” Ugh:
It wasn’t Leonardo DiCaprio’s birthday this weekend … but it sure felt like it … he was seen going straight up “Wolf of Wall Street” on Rihanna at the Playboy Mansion.
It’s a good thing for Leo … designer Nikki Erwin had boyfriend/producer Chuck Pacheco — “Alpha Dogs,” “My Sister’s Keeper” — invite him to her star-stacked 30th B-Day at the Playboy Mansion Saturday … and our spies tell TMZ, Cap and RiRi were gettin’ super steamy and even swapping spit.
A friend of Leo’s tells us the kissing didn’t happen … but 2 people who were there say it did. BTW … not that there’s anything wrong with it.
The two apparently seemed very comfortable getting hot and heavy around stars like Paris Hilton, Hilary Duff, Tom Hardy, Pamela Anderson, Naomi Campbell, and Tobey Maguire.
It’s not clear if they left together but we’re told they ended up at the same after-party — along with 50 Cent — and things got even hotter.
[From TMZ]
You know, I already get grossed out at the thought of a Playboy mansion party. All those germs. Now there’s the added visual image of Rihanna lowering herself to make out with Leo. Not that she wouldn’t go there. I can see her thinking it might be hilarious. She’d never take it seriously. Okay, I changed my mind and sort of want this story to be real. Someone needs to mess with Leo’s ego. Rihanna may be the girl who could make it happen.
Dicaprianna in 2015!
Photos courtesy of Fame/Flynet & WENN
Somewhere, Drake is gazing out into a window…. Whispering “it hurts….”
Lmao!!!
Lol this makes me want to look at Drake memes all day.
Ya’ll @StuffDrakeDoes on Twitter is The Gold You seek
The Only Hooking up Leo needs to be doing is with a Shower and a Barber… But I bet the Entire VS Catalog is heartbroken at this hook up posibility
I read on lipstick alley that he basically has his own harem? There were pics and all of all the girls he’s regularly seen with
You mean VS isn’t his harem?? I wish she would just make better choices in men, my goodness. He is so gross.
Love the makeup in that top pic, but is she trying for hooker chic?
I was talking about Drake
Ugh thinking about The Bloke partying with Paris Hilton at the playboy mansion is making my skin crawl.
And yes of course Rihanna can do better. I hate thinking of Leo’s hobo beard rubbing up against her beautiful face.
Right? Are we sure The Bloke was really there?
I always got the impression that he wasn’t into the celeb party scene.
Him and Leo are filming a movie together right now, so I think that’s why they’ve been hanging out more. BUT Tom has been partying more with Leo which doesn’t exactly bode well if he wants to keep his long-term sobriety in check.
There have been rumors about Leo and Rihanna for years.
Going back to when she was spotted sneaking out of his LA pad in 2008.
They also mix and club in the same circles, as recently as pictured together in St Barts, this New Years Eve.
Of course Rihanna *could* do better, but the question has always been…does she really want to?
Yep, true enough.
“I hate thinking of Leo’s hobo beard rubbing up against her beautiful face.”
Me too. I imagine it smells like the nasty rag bartenders use to wipe up spilled beer. I can’t imagine getting my face NEAR that vile beard!
Ewwwwww! LOL
Rihanna puts the o in ho. Of course she did this. I dont know where you guys plucked the “smart princess” image from but she is ratchet. And I do mean sleep with Di Caprio type of ratchet.
I do agree with you
Exactly.
Yup. This. She is gross.
Lol wtf….
Leo is constantly surrounded by dozens of models half his age and we know hardly anything about Rihanna’s love life, but she’s the ho?
@bns – They are as bad as each other.
And with same nasty habits.
I know, right???
Thank you BNS!
Rihanna’s been linked to maybe five guys but she’s the “ho”. I don’t see those people pulling this double standard crap on Taylor Swift posts.
+10,000
Okay, she’s not a ho, and I don’t onow what rachet means, but she seems like such a nasty person.
Pfffft wtf is right. With bns on this one.
I guess being gorgeous, successful, sexy, confident and female makes you a ho. If I had to drink out of the same glass of one them, I’d pick Rihanna without a second thought.
She not a ho, but apart from her beauty, I can’t seen anything appealing about Rihanna. She seems so shallow, narcissistic, and, judging by the way she treated that girl who had a prom dress similar to hers, she’s also a mean person.
At lest Leo seem like someone you could have a conversation with.
And he’s talented, she isn’t. Not that it matters when it comes to them hooking up.
Lmao. You ladies need to spend more time on urban gossip sites. Rihanna isnt just a yacht model for Daily Mail. She is a known hit-and-run girl. She doesnt even discriminate either, she’ll bang guys who roll together and be like “what?”.
The only difference between her and Di caprio is that mainstream (i.e. white media) doesnt broadcast her crap.
@Skepticintheroom
Lol do you hear yourself? So, it’s true that she’s a ho because a GOSSIP site told you? And by urban, I hope you don’t mean MediaTakeOut because if you do then this convo is over.
@Charlie
Sure, you can have a conversation with Leo… as long as you’re a man. He’s not interested in whatever women have to offer in conversation, I think his dating history proves this much.
@bns
Took those words out of my keyboard 😛 mediatakeout is hilarious
Cue the people mad at you for ho shaming! But for real, Leo likes them really young and super skinny. Rhianna is thin by real standards, but if you’re not the type that a 00 is hanging off of, he’ll pass.
No one is mad, and it’s not ho shaming when you don’t even have enough evidence to prove that the person in question is actually a ho.
I won’t call her a ho, but I will agree there’s a lot of really ‘optimistic’ people judging her against Leo. Riri has never been ashamed to get down and get wild with cameras present so it’s not exactly a big ol secret.
But does that make her less of a person? It seems to be that she’s being condemned for being sexual. (Not by you, but by some other posters). It seems to me that she just does what many men do, but people have to belittle her while the man’s behavior is fine, boys will be boys, but people are lining up to stone her. That kind of thinking has held women back for centuries.
Good lorde!! No one wants this to be true, cause GROSS. But why does that make ker a “ho”? Bad tase if true, yes. But if anyone has a right to that title, it’s Leho. Come on, Riri does what she wants, but Leo has a ball pit he fills with barely legal models and dives in.
those typos!!! awful.except for Leho,which i meant. don’t text and do brain surgery, kids.
@Danielle Leos been around the block and back for 20 years, in his 40s and living like an ageing playboy, but you choose to call Rihanna a ” ho”? Misogyny is well and truly alive. Smh.
RiRi is game. Yes, of course she might do Leo and one of his models too.
I think she’s bi anyway.
I’m on the same page as you, Bedhead. Rihanna is probably one (of very few woman) who could just leave Leo a whimpering wreck.
Let the games commence….
#Dicapriannain2015
I dunno, it’d break my heart to see her this body on a fat old guy. Besides, why do you think he dates 20-year-olds? It’s not just their tight asses that he goes after. She’d eat him alive.
*WASTE this body
I believe it she likes douchey men.
MAKE THIS HAPPEN!
I’m totally yelling this like Gerard Butler in “300”….
Less loincloth wearing at my end, thank god 😜
I’m sure you can rock a loincloth Kali.
@ mia girl – hahaha thank you but trust me, after the amount of food eaten at Christmas, loin cloths are best left alone….
+1000!!
I hope she hit and quit it.
Nooooo Rihanna, noooooo
So no more blue-eyed blondes for Leo? he used to be hot, now not so much. Rihanna can do better but she has a thing for douches so who knows.
Do you actually think he would date her it’s called a hook up and Leo’s done it with half of Holywood for the last 20 years and from what I’ve read Rihannna loves a fuck /hook up, especially with Hollywood actors , I remember years ago watching her make out at a after party in Toronto with Shia Lebeouf and that before she became really famous .
One of my local radio DJs tells a story about seeing him in cuban clubs in NYC all the time (this is maybe 15 years ago?). He says it seemed like Leo was interested in women of any race. Although, he only publicly dates the blond VS models, which is shtty.
That guy looking at Leo D in the last pic is probably thinking ” What do women see in this guy? “
Money and fame.
And he might be a blast to hang out with if you’re a barely-twenty-something who just wants to party in expensive ways with no strings attached. Who knows.
I got itchy all of a sudden. I would so have hit it in the titanic and Romeo + Juliet era. Now? Not even with antibiotics in tow.
Ewww!! Are these younger girls hoping that Leo Crapio (my daughter calls him that! Haha) guy would turn just like Mr.Kentucky soon and want to be around just in case?
I am bajan, just like rihanna. I think they would make a fantastic couple.
He like to use girls like the taking tissues out of a tissue box, and rihanna loves a man who like to tell what to do. So yeah I think they would make a lovely couple.
Just as long she stays away from sweet men like Tom Hiddleston, I am quite happy.
After reading a few books about the playboy mansion ( bunny tales and playground – good read btw ) any little bit of curiosity about the place left. Apparently it’s a big sh*thole trapped in 1970 so I don’t get why these celebrities even want to party there anymore. Maybe they look at it the way I look at a good dive bar , it’s fun to slum it every once in a while – you just know better than To actually sit down anywhere lol Who knows but Gross.
As far as Leo amd Riri that would be some good gossip if they were to start hooking up on the regular. Hot messes
The Playmate who tweeted about Leo and Rihanna, had to delete it cause to live in the Playboy mansion requires strict confidentiality contracts.
You see nothing, You hear nothing.
Which is why so many celebs like going there, safe that their debauchery will stay within the mansion walls.
My friend’s husband does lighting for television shows and he says the playboy mansion smells like pee! Apparently there are many pets and they just go in the house. Yuck. Besides the smell, he says that it is very 70s and dated.
I picture cosby & hef wandering around in robes so of course it smells like stale urine from the 70s (it might be them & not the 1 pound chihuahua). The only people I think of wanting to party there these days is Tara Reid, David Hasselhof, Paris Hilton & Verne Troyer.
I don’t care about the (alleged) hook up, but GOTDAYAM she is SO gorgeous.
Word.
Nah. She’s not a VS model, she’s 26 and she’s fond of drama in relationships… I don’t think she’s quite his type (then again I would think higher of him if it were true).
I hope this happens just so we can keep calling them Dicaprianna!!! Love it!!!!
DicapRIHo*
😀
Leonardo may not be attractive like he used to be, but I’d sleep with him out of curiosity.
Rihanna can do better than Leo? I think he’s a immature guy who’s looks are fading and who picks his girlfriends out of the VS catalogue and even I can admit he’d probably be the best guy she’s hooked up with ever.
Pfft. Rihanna has sht taste in men. Drake, Chris, Mat Kemp…users and abusers. Leo would be a step up on the escalator to the bottom.
Well Rihanna has done worst, and honestly I think she is hotter then all the VS Leo has dated recently.
Y all putting Leo down… Whts so good bout banging riri?? Half industry done had dat, lov Leo, especially in titanic !!
I don’t have much of an opinion on if they did/didn’t, but sort of off topic, can’t this guy get his heart broken just ONCE? Just. one. time. That is the only appropriate karma I could see for his grossness. I wanna see him fall in love, get dumped, cry, stalk, mope around and generally just have one f*ing emotion just once. Sadly, it’ll never happen.
“Doesn’t have the best taste in men”- understatement of the year! She can only go up from her past so Leo might be a prize….I would actually love to see them together for some odd reason.
Anyone else think these stories about Leo are too convenient? I know he’s not promoting anything BUT what if these are planted by him? Taylor Swift and Rihanna want to or have hooked up with Leo? I highly doubt that, he’s looking like a bag of hot garbage lately, i think he’s planting these stories to make himself still seem wanted.
I think LD is a classic commitmentphobe. Multiple long term relationships that he always exits. He doesn’t allow himself to be vulnerable enough to get his heart broken.
GROSS.
All over gross, and he’s looking especially gross lately too.. ugh.
Seriously. If she wants to get her rocks off with Leo, so what? They are both living in the delusional world of celebrity. I would happy to know there was an honest connection. Do I expect it? No. But they are who they are.