Jade Bahr

Interesting list. Was it ever posted? 10 Women Leonardo DiCaprio Is Close To (5 He Stays Away From) He exudes street-savvy with just a touch of sophistication, and it seems to work in his efforts to get close to the ladies. For better or worse, Leonardo DiCaprio might, just might, be described as a man's man. Not so much macho, as swaggering, cocky, and full of himself. He exudes street-savvy with just a touch of sophistication. And it's just true to say that he's dated more 20-something supermodels than just about anybody else out there. As Tina Fey once quipped, introducing Leo at an awards show, "And now, like a supermodel's v*****, let's all give a warm welcome to Leonardo DiCaprio." Even Leo was in stitches over that one. It's funny because it's too true. It's fair to say that he has been, until now at least, a love 'em and leave 'em kind of guy, the kind of entitled man who thinks he can have any woman he wants. That means he's made a lot of enemies in the modeling world. Not surprisingly he's also made quite a few female friends along the way. Some of them will surprise you. Here are 10 women that Leo is close to And 5 he would probably run across the street to avoid. 15 Close - Kate Winslet In 1997, Kate Winslett and Leonardo DiCaprio made Titanic together. The dynamic acting duo has remained true friends ever since. Leo has called her a great actress and said: "We just like each other as people." Their chemistry onscreen in Titanic was strong and undeniable. But Leo has said the love scenes gave them the giggles big time. 14 Close - His Mom A boy's best friend is his mother. Right? Well, if the boy is Leonardo DiCaprio, that is absolutely the case. His mother Irmelin Indenbirken raised him on her own in Los Angeles after she split with his father. It was a financial struggle, the result of which is that the two have developed a strong and lasting bond. She is often his "date" at events. 13 Stay Away - Cara Delevingne So, in 2013 38-year-old Leonardo was at the Cannes Film Festival to promote his film The Great Gatsby. He runs into the 20-something model Cara Delevingne and fancies her like mad. Come up to my room he says. No, no, no she says. Seems she thought he was too cocky and (wait for it) too old! Ouch. And that was 7 years ago. Good one Cara! 12 Close - Camila Morrone 25-year-old Camila Morrone and Leonardo DiCaprio dated for five years. That's a long time for Leo. And it turns out they are still on good terms – so much they hang out even after their breakup! Why is that? Before anyone begins to speculate they are potentially rekindling their relationship, that is not the case. Apparently, the exes still co-parent their dogs which they first fostered and finally adopted while they quarantined together in 2020. 11 Close - Margot Robbie She is beautiful, talented, and fun to be around. From the time Leo watched her audition for The Wolf of Wall Street Leonardo has been a big fan of the Aussie actress. They have done three films together, including 2019's Once Upon a Time In Hollywood. The pair seemed to have bonded along the way and display an easy-going, relaxed friendship. It doesn't hurt that Robbie is drop-dead gorgeous. 10 Close - Cameron Diaz From the time Cameron Diaz and Leonardo DiCaprio worked on 2002's Gangs of New York, they have been firm and fast friends. They always seem happy to see one another when they find themselves at the same place at the same time. Are they more than friends? No. Leo doesn't "do" actresses and Cameron is 47-years-old. Leo likes 'em young. Very young. 09 Stay Away - Nina Agdal Is it a coincidence that shortly after Leonardo DiCaprio broke up with model Nina Agdal in 2017, he hooked up with Camila Morrone at Cannes Film Festival? Some think it is more than a coincidence. So, he dumped a 25-year-old in order to make way for a 19-year-old? Got it in one. We'd stay away from Nina if we were Leo. 08 Close - Naomi Campbell For once in his life, Leonardo was a boy toy when he dated supermodel Naomi Campbell in 1995. He was around 20-years-old and she was 25! It was a first (and probably a last) as far as Leonardo DiCaprio was concerned. They have remained friends and can be spotted chatting and sipping champers on some yacht or another in places like Cannes. 07 Close - Drew Barrymore Leonardo DiCaprio came into Drew Barrymore's orbit due to their mutual friendship with actress Cameron Diaz. She has gushed over his talent and his accomplishments. Leo and Drew are the same age and were both "up and coming" Hollywood stars in the late 1990s. So, their paths crossed often. They have gone from up and coming to established together. 06 Close - Jennifer Aniston We all know about the Brad Pitt/Leonardo DiCaprio bromance. Well, in the past Jennifer Aniston and Leo's paths have crossed again and again. She was even at his 44th birthday bash in Los Angeles in 2019. Many try to link her with Leonardo romantically. No way. As we said, he isn't into dating actresses and she is just way too "mature". Besides, the tabloids are busy marrying her off to Brad . . . again. 05 Stay Away - Lady Gaga A few years back, Leonardo DiCaprio ran into Lady Gaga at the Golden Globe Awards. Well, it was actually the other way around. She was intent on getting to the stage to accept an award when she brushed past Leo. He pulled quite a face. Was he dissing the singer/actress? Some think so. Steer clear, Leo. Steer clear. 04 Close - Beyoncé He rolls up to fundraisers for her foundation. She and Jay-Z were invited and attended DiCaprio's 44th birthday party. The couple doesn't usually do that kind of Hollywood party thing. So, it's a sign of the friendship between Beyoncé and Dicaprio that she was there. Seems, Queen Bee and Hollywood's number one bachelor have become good friends. 03 Stay Away - Toni Garrn How would you feel if you were a 20-something German model who in 2014 was supposedly loved up with Leonardo DiCaprio and the guy left you at a party, departing with 20, count them, 20 other women? Not surprisingly, the split came soon afterward. We don't think Leo is on Toni Garrn's list of best chums, to say the least. The mind boggles. Leo and 20 women? 02 Close - Gwyneth Paltrow Back in the 1990s, they were Hollywood mates, maybe a little more. He talked dirty to her. No, it's not what you think. He told her that red meat was disgusting and dirty. Like with Drew Barrymore, Paltrow and DiCaprio were up and coming together, their paths often crossing. They'd take in a movie together or go out for a meal. It's hard to believe they were ever that young and fresh-faced. Time flies. 01 Stay Away - Aretha Wilson It's 2009 and Leonardo is at a Hollywood party at producer Rick Saloman's house when, out of the blue, a Canadian model by the name of Aretha Wilson smacked him over the head with a smashed bottle. He had to have stitches. It's not clear why she did it. But what is clear is that she was tried, convicted, and served jail time. This one is definitely one to avoid at all costs. Source

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Guess who's aries? LOL by Xavi Gordo

^I think most people are even the ones claiming hating him are deeply obsessed with his love life LOL

Lainey making a brief summary of all exes people who showed up separately and kinda have a connection to Leo LOL Single Models and Bradley Cooper... and Leo DiCaprio Irina and Bradley did spend time together inside the event… …and no one can say for sure whether or not they’re on again or if they’re just really close co-parents. But remember, a couple of weeks ago at Coachella, Irina was hanging out with BCoop’s good friend Leonardo DiCaprio, leading to speculation that there might be something going on there. So if we’re bringing it full circle, Gisele was with Leo in the way back so why can’t Bradley and Gisele be a thing in the now? While we’re here, we might as well continue with the Leo connections and Gigi Hadid...

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Met Gala 2023

Love those photos 🖤

Met Gala 2023

^She looks spectacular. I wish I could pull off a shaved head like this Florence Pugh via Instagram on May 1, 2023 Florence Pugh getting ready for the Met Gala on May 1, 2023

credit to Alana O'Herlihy Laura Polko Patrick Ta Mimi Cuttrell Matthew M Williams

Met after party

Those models are married and/or dating his friends. Geez lol More in the other thread.

^Not exactly "with him" lol

Sry repost whatever lol

Favorite look of the night 🤍 Met Gala 2023

Met Gala after party

LOL

"Poor things" - first look

"Flirtable" is the word people are describing Leos ComicCon look. I've read worse 😄

Martin Scorsese tells Leo DiCaprio at CinemaCon award lunch: “Movies introduced me to everything” *crying in the corner DiCaprio and Scorsese talk 'Killers' as Rihanna hits CinemaCon For Killers Of The Flower Moon, Martin Scorsese wanted to "do right" by Osage people CinemaCon Surprise: Leonardo DiCaprio Shows Up for Martin Scorsese Honor With Killers Of The Flower Moon, Martin Scorsese Wanted To Understand Complicity In Genocide [CinemaCon 2023]

I guess we're all gettin old. At least we do it together LOL

Damn that's the nicest surprise in a long time Welcome back working Leo. We missed you