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Kylie Jenner and Timothée Chalamet Make Red Carpet Debut in Rome
Camila Morrone’s heart will go on for a new man in her life.
Nearly three years after the end of her four-year relationship with Leonardo DiCaprio, the Daisy Jones & the Six alum debuted her new romance with Cole Bennett in a sweet birthday post.
Camila, 27, celebrated the music video director’s 29th birthday with a series of snaps shared to her Instagram Story May 14. In one pic, she playfully squeezed a shirtless Cole’s cheeks, making his lips pursed while he stared into the camera. She captioned the photo simply, “Happy birthday baby.”
Other pics included in Camila’s celebration of the director—who has frequently collaborated with Eminem, Drake, Doechii and Lil Yachty—were candid looks at Cole eating ice cream, drinking from a bottle on the beach and taking a mirror pic in the bathroom together. Across the photos, Camila referred to Cole as the “coolest ever.”
Though this is the first time Camila has featured her new boyfriend on her social media, the pair first fueled romance rumors when they stepped out together in July. Around that time, they joined the Never Goin’ Back star’s bestie Kaia Gerber and her then-boyfriend Austin Butler for a double date in New York City.
While Camila—whose mom Lucila Solá, 49, dated Al Pacino, 85, from 2008 to 2018—has been fairly private about her current relationship, the 27-year-old wasn’t shy about discussing her very public relationship with Leo, including addressing others’ critiques of her and the Titanic star’s two-decade age gap.
"There's so many relationships in Hollywood—and in the history of the world—where people have large age gaps,” Camila told The Los Angeles Times in 2019. “I just think anyone should be able to date who they want to date."
Camila Morrone/Instagram
Noting that she understood the interest in her relationship and "would be curious about it too,” Camila added, "There should always be an identity besides who you're dating."
"I understand the association,” she continued, “but I'm confident that will continue to slip away and be less of a conversation."
Read on for a deeper dive into the ocean waters of Leo’s dating history.
DMI (Dave Allocca)/The LIFE Picture Collection via Shutterstock
Bridget Hall
The first model Leo reportedly romanced? Victoria's Secret model Bridget Hall, with the pair attending several events together in 1994. But her agent at the time denied any rumors that they were anything more than friends, saying, "I remember him. He was such a twitty little guy. They were friends, this is so so not true."
DMI/The LIFE Picture Collection via Shutterstock
Kristen Zang
While Leo rarely walks the red carpet with any of his significant others, he was hand-in-hand with actress Kristen Zang at the 1996 premiere of Romeo + Juliet. The couple dated for two years before they split in 1998.
Dimitrios Kambouris/Getty Images for Make-A-Wish Metro New York
Vanessa Trump
In 1998, around the height of his post-Titanic fame, there were rumblings Leo was romantically linked to Vanessa Trump. However, his publicist Cindy Guagenti firmly said otherwise and told New York Magazine that year, "He never dated her."
Vanessa wed Donald Trump Jr. in 2005 and they went on to welcome five children together: Kai, Donald, Tristan, Spencer and Chloe. But in 2018, the couple filed for divorce, which was finalized the following year. In March 2025, Vanessa confirmed she’s dating Tiger Woods.
Frank Micelotta/Getty Images
Gisele Bündchen
How serious were Leo and Gisele Bündchen when they were together? Well, she is the only woman he's dated to ever walk the red carpet with him at the Oscars.
Leo and Gisele dated on and off from 1999 through 2005, becoming one of Hollywood's hottest and most private couples. But in 2005, the Brazilian supermodel made the decision to walk away. And then, in 2019, she finally opened up about the breakup, revealing she was struggling with panic attacks and knew she needed to change her lifestyle.
"No longer numbing myself with smoking, drinking and too much work, I was becoming more and more aware of things that I'd chosen not to look at," she reflected to PORTER at the time. "Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes."
But in the end, it all worked out. In 2009, Gisele married Tom Brady, with her becoming stepmom to his son Jack from his previous relationship with Bridget Moynahan and later welcoming kids Benjamin and Vivian. However, the runway star and the former quarterback divorced in 2022.
She's since found love again, welcoming her first baby with Joaquim Valente in 2025.
As for Leo, he moved onto another serious relationship...
Noel Vasquez/Getty Images
Bar Refaeli
In 2006, Leo began romancing Sports Illustrated swimsuit model Bar Refaeli, who was 11 years his junior.
The pair split for six months in 2009, with Bar later explaining she needed that time apart. "It was a half year for which I am very grateful," the Israeli supermodel told L'Isha magazine. "I came to understand a lot of things about myself."
Such as? "I worked on myself [and] I grew up," Bar continued "I didn't know what 'alone' was like. Today I know that a relationship can work only if you know you can be alone and you are not afraid. Today I'm not afraid of being alone."
By 2010, they were sparking engagement rumors, but a source shot down the reports to E! News. And by mid-2011, the couple split for good.
Bar went on to marry businessman Adi Ezra, with whom she shares kids Liv, Elle and David.
Revolver / BACKGRID
Blake Lively
Spotted in May 2011: Hollywood's most in-demand actor and TV's It Girl getting cozy on a yacht in Cannes.
Yes, before Blake Lively married Ryan Reynolds, she dated Leo.
After first being seen together at the glam film festival—months after they reportedly met—the Gossip Girl star, then 24, and Leo, then 36, were photographed on dates and engaging in PDA in Italy, New York and Australia.
Alas, after just five months, the hottest couple of summer 2011 was dunzo, with a source telling E! News that the split was amicable.
BACKGRID
Erin Heatherton
Following his whirlwind romance with Blake, Leo began dating Victoria's Secret model Erin Heatherton in early 2012, with the pair being photographed zip-lining in Mexico with his mom, Irmelin. However, they had split by November.
In 2023, Erin wed Karol Kocemba. The couple welcomed daughter Eila Violet the following year.
FameFlynet / BACKGRID
Toni Garrn
Leo was first spotted with the Victoria's Secret model Toni Garrn in 2013 when they were photographed kissing on a yacht in Ibiza. (Fun fact: This was the trip Leo infamously tried flyboarding.)
By 2014, the couple had enjoyed lavish vacations to Bora Bora, the French Alps and St. Barts. Plus, the German model attended a Golden Globes after-party with the star. In an interview with GQ, a then-22-year-old Toni looked forward to starting a family one day, though she didn't mention Leo: "I always wanted four kids. But we'll see. We'll start with one at some point, I don't know."
But after 18 months, it was confirmed the pair had split in December 2014.
However, they reportedly rekindled their romance briefly in 2017 when they were photographed together in NYC. But ultimately, they both moved on. Toni was married to Magic Mike actor Alex Pettyfer, with whom she shares daughter Luca, from 2020 to 2023. The following year, she sparked romance rumors with Joshua Phitoussi.
Best Image / BACKGRID
Kelly Rohrbach
Leo dated Victoria's Secret model and Baywatch star Kelly Rohrbach in 2015, but they called it quits after 18 months.
"This is a really busy time for both of them," a source told E! News at the time. "They are both just so busy that it was hard to make a relationship work They are still very friendly. They really enjoy each other's company."
In 2021, Kelly wed businessman Steuart Walton.
Jesse Grant/Getty Images
Rihanna
The Internet nearly shut down when photos emerged of Leo and Rihanna getting very close at Coachella in 2016, with the pictures coming just a year after the two reportedly were kissing at a Playboy Mansion Party.
So when the "Umbrella" singer and the Titanic actor were spotted together once again at Coachella's Neon Carnival, the rumor mill ran rampant.
But a source denied the pair were an item. "They are friends and still hang out," the insider told E! in 2016. "They both like the same type of music and that's usually when they run into each other. Neither of them are looking for any type of relationship now."
In 2019, Rihanna began dating A$AP Rocky, with whom she shares kids RZA and Riot.
SPOT / BACKGRID
Nina Agdal
While Leo was first linked to Nina Agdalthe as early as 2014 (when they were spotted at the same Super Bowl party), the Danish model shot down romance rumors.
"I've never met him, but I have a friend who got invited to dinner with him," she told Cosmo. "But, you know, whatever. It's kind of the group you interact with, people that you meet at parties, so that would be only natural."
But by May 2016, Nina and Leo were an item, with a source saying, "They have great chemistry and laugh a lot." Alas, after a year together, including vacations to the Bahamas and Montauk, their romance ended in May 2017.
BACKGRID
Camila Morrone
But it turns out Leo was actually ready to get a bit more serious as he started dating girlfriend Camila Morrone in April 2018, with the duo being spotted engaging in PDA at Coachella that year (though they were first photographed together in December 2017).
While Leo's romance with the Daisy Jones & The Six actress started off "relaxed," a source told E! News in November 2018, it was "getting more serious. They've been inseparable for the last year and are crazy about one another. They've gotten to know each other's families and they love being together."
Camila continued to support Leo at events for his 2019 movie Once Upon a Time...in Hollywood, with him returning the favor by playing Instagram Boyfriend for her during their time at Cannes.
"I saw the meme," Camila later told Vanity Fair. "Poor thing, he's being called an Instagram boyfriend. He's an environmentalist and a movie star and it doesn't mean a thing!"
But after more than four years together, the couple split in 2022.
"Distance played a factor," a source said in August 2022, adding that the romance "ran its course."
However, their hearts did go on. In July 2024, reports spread that Camila had struck up a romance with music video director Cole Bennett.
Taylor Hill/Getty Images, Amy Sussman/Getty Images
Gigi Hadid
After his split from Camila, Leo sparked romance rumors with Gigi Hadid in the fall of 2022. However, a source close to him told E! News that September The Revenant alum was "enjoying being single" and that he and the model were “not exclusive.”
And an insider noted that Gigi, who is mom to daughter Khai with ex Zayn Malik, was in a similar mindset.
"Gigi and Leo are having a lot of fun right now," the source close to her told E! that October. "They have been trying to stay low-key and private and she has been enjoying the time they have been spending together."
But over the next few months, the two continued to make headlines with their various dinner outings in New York and Italy. They also both attended star-studded events like a pre-Oscars celebration and a Met Gala party in the spring of 2023. And that June, Gigi was spotted at the same London restaurant as Leo and his parents.
However, the runway of their time together didn’t stretch much longer. Leo sparked romance rumors with Vittoria Ceretti in August 2023, and Gigi later began dating Bradley Cooper.
VALERIE MACON/AFP via Getty Images; Gilbert Flores/Variety via Getty Images
Vittoria Ceretti
Leo and Vittoria Ceretti first sparked dating rumors in August 2023 and have continued to keep much of their bond private, with them being spotted on only a couple of public outings.
"If I've learned anything, it's that there's nothing more precious than what we don't know about you," the model told Vogue France in an interview published March 24. "Preserving a part of your life for you and your loved ones is a luxury many in our professions don't have. So I cherish my secret garden.”
However, Vittoria expressed how she tries not to let the public attention get to her.
"If what you're experiencing is real, if you know you love each other, then there's no reason to be alarmed," she added. "Love protects and gives confidence."
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