Leo’s a great actor, you can’t deny that. But his dating history has been so extensive and kind of predictable that it basically became a meme. Now we all jokingly predict the demise of each of his relationships the moment his model girlfriend turns 25. But has it really always been that way? Were there any exceptions? Is there any sign of change now that he’s gotten older?
1994: Bridget Hall
Leo’s first major rumored romance was with model Bridget Hall. At the time, he was fresh off What’s Eating Gilbert Grape and just entering the public eye. The New York press hinted that the two hooked up, but by 1998 Hall denied it ever happened, even claiming, “nothing happened.” Tabloids had painted it as a fling gone wrong, but Hall later brushed it off as overblown speculation.
1995: Naomi Campbell
The following year, Leo was linked to Naomi Campbell — and who wasn’t in the ’90s? Their romance was reportedly brief, more of a spark than a full-on relationship, but the two remained close friends. Unlike many of his exes, Naomi kept him in her inner circle, and the pair have been spotted together socially years after the fact.
1996–1997: Kristen Zang
Kristen Zang was one of Leo’s first serious girlfriends. She even spoke candidly to People about their romance, describing him as thoughtful and sweet. They traveled together while he filmed abroad, hung out with each other’s friends, and lived something close to a normal relationship despite the fame. Kristen ended things a few months after her 25th birthday — not that she didn’t notice the timing herself, joking about the “25 rule” in hindsight.
1997: Amber Valletta
Amber Valletta was another one of Leo’s supermodel crushes. The story goes that Leo spotted her in a magazine, asked someone to track her down, and they briefly dated. Neither of them confirmed the romance publicly, but the story has lived on as a classic Leo move.
1997: Helena Christensen
That same year, Leo was also linked to Danish model Helena Christensen. Like Amber, their supposed relationship was more rumor than fact, fueled by the limited tabloid culture of the late ’90s. With little evidence to back it up, this one goes down in history as more speculation than romance.
1998: Eva Herzigová
These two met at the premiere of The Man in the Iron Mask and apparently the connection was almost instant. Eva publicly spoke about DiCaproio, said Leo was a kind man, full of energy, and no to subtly hinted at a memorable first night together. It didn’t last long, but Eva’s rare public comments made this fling more than just a whisper.
2000: Virginie LeDoyen
Leo was linked to his French co-star Virginie LeDoyen since they worked together on The Beach,. Rumor has it that their on-screen chemistry carried over off set, but LeDoyen later dismissed it as tabloid exaggeration. She was far more focused on criticizing the overwhelming media frenzy and said she would “not wish” his level of fame on anyone.
2000–2005: Gisele Bündchen
Then came his first truly long-term relationship: five years with Gisele Bündchen. At the time, they were one of Hollywood’s hottest couples. After their relationship ended, Gisele wrote a memoir in which she revealed that while she was growing spiritually and personally, Leo generally stayed the same. So in the end she decided to move on. But but she credited the relationship with teaching her a lot about herself.
2005–2010: Bar Refaeli
Not long after Gisele, Leo started dating Israeli model Bar Refaeli. They were together on and off for about five years, meeting at a U2 party and quickly becoming a paparazzi staple. According to reports, the relationship ended when friends and family pushed for marriage and Leo wasn’t ready to commit.
2011: Blake Lively
In a surprise detour from models, Leo briefly dated actress Blake Lively. Their fling started during the Cannes Film Festival and ended within a few months. Sources blamed “distance and timing,” which seemed convenient since Blake quickly moved on to her now-husband, Ryan Reynolds.
2012: Erin Heatherton
Leo kept the Victoria’s Secret streak alive with Erin Heatherton, and for almost a year in 2012, they looked picture-perfect. Their breakup was refreshingly low on drama — by Hollywood standards, practically boring. Erin never bad-mouthed him afterward; in fact, she said she was happy, which pretty much tells us this was one of Leo’s rare “clean exits.”
2013: Toni Garrn
Next came German model Toni Garrn. They kept things mostly under wraps, but whispers of a breakup got louder after Leo was spotted leaving a Miami nightclub with about 20 women in tow. Whether that was the nail in the coffin or just tabloid flair, Toni didn’t stick around long after.
2016: Kelly Rohrbach
Kelly Rohrbach, a Sports Illustrated model, had one of Leo’s most meme-worthy flings. The two were photographed biking all over New York City, looking like a rom-com in motion. But it didn’t last — apparently, their busy schedules got in the way. Still, sources insisted it ended on friendly terms.
2016–2017: Nina Agdal
Danish model Nina Agdal was up next, and their relationship lasted about a year. There were vacations, paparazzi shots, and the usual whirlwind. When it ended, the word “amicable” popped up again — Leo’s favorite breakup adjective, apparently.
2017–2022: Camila Morrone
Now this was the game-changer. Camila Morrone dated Leo for nearly five years — practically a decade in DiCaprio time. They were serious enough that engagement rumors circulated, and Leo was said to be “very in love.” Camila even addressed the elephant in the room: their 23-year age gap, telling critics to judge the relationship itself instead of her birth certificate. When it ended in 2022, the internet immediately revived the “25 rule” meme — because, yep, she’d just hit that number.
2022: Victoria Lamas
Right after Camila, Leo was linked to actress Victoria Lamas. Her dad confirmed she was “smitten” but warned her to treat the fling like a holiday romance — fun while it lasts, but don’t get too attached. Turns out, Dad was right.
2022: Eden Polani (Rumored)
Around the same time, Leo was spotted next to 19-year-old model Eden Polani at a party. Cue the headlines. A source swore nothing was happening, but just sitting beside someone under 20 was enough to reignite his reputation as Hollywood’s Peter Pan.
2022–2023: Gigi Hadid
This one actually surprised people. Leo and Gigi Hadid made headlines in late 2022, and for a second, it looked like he might be breaking his type. They were spotted together more than once, but sources clarified it was casual. By early 2023, they were doing their own thing, and the romance fizzled out.
2023–Present: Vittoria Ceretti
Finally, Vittoria Ceretti. The Italian supermodel entered Leo’s orbit at Cannes in 2023, and things escalated quickly — ice cream dates in L.A., steamy nights in Ibiza, the works. By the end of that year, he was reportedly exclusive (a rarity in Leo-world), and as of 2025, they’re still going strong. Vittoria has even spoken about what it’s like to date someone as famous as him, saying love makes her feel secure. Translation: this might actually be the real deal.
The Big Picture
So what’s the verdict? Leo’s track record is heavy on models, light on longevity, and almost obsessively tied to the age of 25. But with Vittoria Ceretti, he seems to be rewriting his own script — or at least, stretching past the meme. Whether it sticks? Well, only time (and the next Cannes Festival) will tell.
