"Once Upon a Time in Hollywood is nearly three hours long. Leonardo DiCaprio attended the premiere, and by the end, his date was too old for him.” This is an old joke, but it is still funny.
Leonardo DiCaprio is one of the most famous and talented actors in Hollywood. But his talent goes much further than acting.
He is quite the ladies' man. Over the years, his relationships have filled the yellow-press pages.
He is known for preferring models (super and regular). And the older he gets, the younger the models are.
To be honest, he has accomplished a lot, and all men envy him. He's been in high-profile romances with the likes of Gisele Bündchen and is said to even have dated Rihanna. His dating statistics speak for themselves: most of his dates are younger, blonde, and have walked Victoria's Secret catwalk.
He's now dating Camila Morrone, a 23-year-old model/actress with whom he's been associated since 2017. It is clearly a committed relationship. This puts the Oscar winner's perfect score as a bachelor in jeopardy.
We have compiled a list of 12 beauties he has dated over the years, and we simply can't decide which one is prettier. Take a look:
1. Bridget Hall
Victoria's Secret model Bridget Hall was the first model Leo is said to have dated, with the two attending many events together in 1994. However, at the time, her modeling agent refuted any suggestions that they were anything more than pals, adding, "I recall him. He was a funny little fellow. This is not true. They were pals."
2. Kristen Zang
While Leo rarely walks the red carpet with any of his significant others, at the 1996 premiere of Romeo and Juliet, he strolled hand-in-hand with the actress Kristen Zang. Kristen reportedly ended their relationship in 1998 after two years of dating.
"She is the love of his life," a friend of Kristen's said at the time to The New York Daily News, adding, "She thinks he needs to grow up."
3. Gisele Bundchen
When Leo and the world's most renowned supermodel dated for five years, how serious were they? She is, after all, the only woman he has ever dated who has ever accompanied him to the Academy Awards.
From 1999 until 2005, the couple dated on and off for six years, becoming one of Hollywood's hottest and most discreet couples. The Brazilian model, however, decided to leave in 2005.
Then, in 2019, she eventually told PORTER about her breakup, stating she was suffering from panic attacks and felt she needed to make a lifestyle change.
"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. Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes."
4. Bar Refaeli
In 2006, he began dating Bar Refaeli, a Sports Illustrated swimsuit model. She was 11 years younger than him.
In 2009, the couple parted for six months, with Bar later telling L'Isha magazine that she wanted the space.
"It was a half year for which I am very grateful," the Israeli supermodel explained. "I came to understand a lot of things about myself. I worked on myself and I grew up," Refaeli said
"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 mid-2011, the couple split for good.
5. Blake Lively
The Gossip Girl star dated Leo before marrying Ryan Reynolds. Leo, then 36, and Blake, then 24, were photographed on dates and engaging in PDA in multiple locations, including Italy, Disneyland, New York, and Australia, after first being spotted at the glam film festival (and reportedly meeting the previous November at a dinner for potential cast members for The Great Gatsby).
They called it quits after being together for only five months.
6. Erin Heatherton
Leo began seeing Victoria's Secret model Erin Heatherton in early 2012, following his whirlwind affair with the Gossip Girl star, and the two were pictured zip-lining in Mexico with his mother, Irmelin. By November, though, the couple had amicably parted ways.
7. Toni Garrn
Leo and Victoria's Secret model were caught kissing on a yacht in Ibiza in 2013, Toni was significantly absent from Leo's 40th birthday event in December 2014, indicating the couple had split after 18 months.
The couple apparently temporarily reignited their romance in 2017 when they were pictured together in New York City. According to a source at the time, "They're simply hanging out and having a good time. It's comforting because it has a history."
8. Kelly Rohrbach
After that, in 2015, came Victoria's Secret model and future Baywatch star, but the couple called it quits after only 18 months together.
"This is a really busy time for both of them," a mutual friend said "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."
9. Rihanna
Photos of Leo and Rihanna getting very close during the 2016 Coachella Music Festival nearly brought the Internet down, coming only a year after the two were said to be kissing at a Playboy Mansion Party. As a result, when they were spotted together again at the Neon Carnival, rumors flew.
However, a source denied that the two were dating.
"They are friends and still hang out. They both like the same type of music and that's usually when they run into each other. Neither of them is looking for any type of relationship now."
10. Nina Agdal
While Leo and Nina were first linked in 2014 when they were seen at the same Super Bowl party, in an interview with Cosmopolitan, Nina knocked off the relationship claims.
"I've never met him, but I have a friend who got invited to dinner with him. But, you know, whatever," the Sport's Illustrated model added. "It's kind of the group you interact with, people that you meet at parties, so that would be only natural. If you're in New York City, you always see him around."
But, Nina and Leo were dating by May 2016, according to a source, and "they have amazing chemistry and laugh a lot." However, their romance had ended in May 2017 after one year together, which included holidays to the Bahamas and Montauk.
11. Bella Hadid
Leo and the model fueled relationship suspicions when they were photographed together at the amfAR charity dinner during the Cannes Film Festival in May 2017, just days after his breakup from Nina. However, at the time, a source stated that both the actor and Bella were "single" and that nothing was going on between them.
"Leo is not on the lookout for a new girlfriend," a source said. "Leo is not looking for another girlfriend," a source explained. "He is just doing Leo. Leo is a flirt, always has been."
12. Camilla Morrone
But it turns out that Leo was ready for something more serious, as he began seeing his current girlfriend Camila Morrone in April 2018, and the two were first seen kissing at Coachella.
While Leo's relationship with the then-21-year-old actress got off to a rocky start, in November of that year, a source told stated that it was "becoming more serious." They've been inseparable for a year and are completely devoted to each other. They've met one other's families and enjoy spending time together."
The couple enjoyed dressing casually.
Camila, unlike some of Leo's former lovers, hasn't been afraid to speak openly about their relationship, hitting back at harsh comments on Instagram after she shared a photo of the late Lauren Bacall and Humphrey Bogart. "A love like this," she wrote with photographs of the couple, who were 20 years apart in age.
Here is one interesting fact for you: The 47-year-old actor has never dated anyone over the age of 25. In fact, three times, he has ended a relationship with a woman before her 26th birthday.
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