How superior were Leo and the world's astir celebrated supermodel erstwhile they were together? Well, she is the lone pistillate he's dated to ever travel him to the Oscars.

The brace dated connected and disconnected for six years from 1999 done 2005, becoming 1 of Hollywood's hottest and astir backstage couples. But successful 2005, the Brazilian exemplary made the determination to locomotion away. And then, successful 2019, she finally opened up astir the breakup to PORTER, revealing she was struggling with panic attacks and knew she needed to alteration her lifestyle.

"No longer numbing myself with smoking, drinking and excessively overmuch work, I was becoming much and much alert of things that I'd chosen not to look at," she reflected in her book, Lessons: My Path to a Meaningful Life. "Was I unsocial successful wanting to bash immoderate superior soul-searching portion helium stayed the same? In the end, unfortunately, the reply was yes."

But successful the end, it each worked out, arsenic Gisele yet married Tom Brady in 2009. Meanwhile Leo moved onto different superior relationship...

In 2006, helium began romancing Sports Illustrated swimsuit exemplary Bar Refaeli, who was 11 years his junior.

The brace divided for six months successful 2009, with Bar aboriginal telling L'Isha mag she needed that clip apart. "It was a fractional twelvemonth for which I americium precise grateful," the Israeli supermodel explained. "I came to recognize a batch of things astir myself. "

"I worked connected myself [and] I grew up," Refaeli continued "I didn't cognize what 'alone' was like. Today I cognize that a narration tin enactment lone if you cognize you tin beryllium unsocial and you are not afraid. Today I'm not acrophobic of being alone."

By 2010, they were sparking engagement rumors, but a root changeable down the reports to E! News. And by mid-2011, the mates divided for good.

Spotted successful May 2011: Hollywood's astir in-demand histrion and TV's It Girl getting cozy connected a yacht successful Cannes. Yes, earlier she joined Ryan Reynolds, the Gossip Girl prima dated Leo.

After archetypal being seen unneurotic astatine the glam movie festival (they reportedly met the erstwhile November astatine a meal for imaginable formed members for The Great Gatsby), Leo, past 36, and Blake, past 24, were photographed connected dates and engaging successful PDA successful Italy, New York and Australia.

Alas, aft conscionable 5 months, the hottest mates of summertime 2011 was dunzo, with a root telling E! News that the divided was amicable.

Following his whirlwind romance with the Gossip Girl star, Leo began dating Victoria's Secret exemplary Erin Heatherton successful aboriginal 2012, with the brace being photographed zip-lining successful Mexico with his mom, Irmelin.

However, they had amicably divided by November. 

Leo was archetypal spotted with the Victoria's Secret exemplary successful 2013 erstwhile they were photographed kissing connected a yacht successful Ibiza. (Fun fact: This was the travel Leo infamously tried flyboarding.)

By 2014, the mates had enjoyed lavish vacations to Bora Bora, the French Alps and St. Barts. Plus, the German exemplary attended a Golden Globes after-party with the star. In an interrogation with GQ, a past 22-year-old Toni looked guardant to starting a household 1 day, though she didn't notation Leo: "I ever wanted 4 kids. But we'll see. We'll commencement with 1 astatine immoderate point, I don't know."

But aft 18 months, it was confirmed the brace had divided successful December 2014. (Toni was noticeably absent from Leo's 40th day bash.)

However, the mates reportedly rekindled their romance concisely successful 2017 erstwhile they were photographed unneurotic successful NYC. As a source told E! astatine the time, "They are conscionable hanging retired and having fun. There's a history, truthful it's comfortable."

Next came the Victoria's Secret exemplary and aboriginal Baywatch star in 2015, but aft 18 months the brace had called it quits.

"This is simply a truly engaged clip for some of them," a root said astatine the time. "They are some conscionable truthful engaged that it was hard to marque a narration enactment They are inactive precise friendly. They truly bask each other's company."

The Internet astir unopen down erstwhile photos of Leo and Rihanna getting precise adjacent astatine the 2016 Coachella Music Festival emerged, which came conscionable a twelvemonth aft the 2 reportedly were kissing astatine a Playboy Mansion Party.

So erstwhile they were spotted unneurotic erstwhile again astatine the Neon Carnival, the rumor mill ran rampant. But a root denied the brace were an item. "They are friends and inactive bent out," an insider shared. "They some similar the aforesaid benignant of euphony and that's usually erstwhile they tally into each other. Neither of them are looking for immoderate benignant of narration now."

While Leo was archetypal linked to the Danish exemplary arsenic aboriginal arsenic 2014 erstwhile they were spotted astatine the aforesaid Super Bowl party, Nina changeable down the romance rumors. "I've ne'er met him, but I person a person who got invited to meal with him," she told Cosmo. "But, you know, whatever. It's benignant of the radical you interact with, radical that you conscionable astatine parties, truthful that would beryllium lone natural." 

Noting that helium "likes blondes," the Sport's Illustrated star admitted they had crossed paths a fewer times before. "If you're successful New York City, you ever spot him around."

But by May 2016, Nina and Leo were an item, with a source saying, "They person large chemistry and laughter a lot." Alas, after a twelvemonth together, including vacations to the Bahamas and Montauk, E! News confirmed their romance had ended successful May 2017.

"They stay successful interaction and stay friends," a root adjacent to the erstwhile mates revealed astatine the time. "It's an amicable split, and they're moving forward."

In May 2017, Leo and the exemplary sparked romance rumors erstwhile they were spotted unneurotic astatine the amfAR foundation gala during the Cannes Film Festival, conscionable aft quality of his divided from Nina broke.

But a source astatine the clip confirmed some the histrion and Bella were azygous and there was thing going on. "Leo is not looking for different girlfriend," a root explained. "He is conscionable doing Leo. Leo is simply a flirt, ever has been."

But it turns retired Leo was really acceptable to get a spot much serious, arsenic helium started dating woman Camila Morrone successful April 2018, with the duo archetypal spotted engaging successful PDA at Coachella (though they were archetypal photographed unneurotic successful December 2017). 

While Leo's romance with the past 21-year-old histrion started disconnected "relaxed," a source told E! News successful November of that twelvemonth that it was "getting much serious. They've been inseparable for the past twelvemonth and are brainsick astir 1 another. They've gotten to cognize each other's families and they emotion being together."

Unlike immoderate of Leo's erstwhile girlfriends, Camila hasn't been acrophobic to casually code their relationship, adjacent clapping backmost astatine hateful comments aft she posted an Instagram of the late Lauren Bacall and Humphrey Bogart. "A emotion similar this," she wrote alongside the pictures of the couple, who had a 20-year property quality betwixt them.

When fans came aft her, she was speedy to respond connected her Instagram Story. "I conscionable work immoderate of the comments connected my Instagram and...my God, radical are truthful mean and afloat of choler with radical that they cognize thing about."

Since then, she's supported him at events promoting Once Upon a Time...in Hollywood, with Leo returning the favor, playing Instagram Boyfriend for her during their clip astatine Cannes. "I saw the meme," Camila aboriginal told Vanity Fair. "Poor thing, he's being called an Instagram boyfriend. He's an environmentalist and a movie prima and it doesn't mean a thing!" 

But conscionable 2 months aft the actress' 25th birthday, the brace called it quits, sources adjacent to the mates confirmed to E! News in August. 

"Distance played a factor," a root said, adding that the romance "ran its course."