Leonardo DiCaprio’s Complete Dating History: From ’90s It-Girl Rumors to Today
Leonardo DiCaprio is one of Hollywood’s greatest actors — but his love life has almost become its own franchise. His dating history is so extensive (and so consistent) that it spawned an entire internet meme: the 25 rule. The running joke? As soon as his girlfriend hits her mid-twenties, she’s out.
But was it always this way? Let’s rewind through Leo’s little black book, from the ’90s supermodel era to his current flame, and see how the legend of “Leonardo the Eternal Bachelor” really unfolded.
1994: Bridget Hall
Leo’s first rumored romance was with model Bridget Hall, fresh off his What’s Eating Gilbert Grape breakout. The tabloids painted it as a messy fling, but Hall later shrugged it off, flat-out denying anything happened. Chalk this one up to gossip column fantasy.
1995: Naomi Campbell
Naomi and Leo were briefly linked (because, honestly, who wasn’t linked to Naomi in the ’90s?). Their spark didn’t last, but unlike many of his other flings, they stayed close friends — and still hang out to this day.
1996–1997: Kristen Zang
Leo’s first real girlfriend. Kristen described him as thoughtful and down-to-earth, and they lived something close to a normal relationship amid his rising fame. She ended things after her 25th birthday — years later joking about the infamous “rule.”
1997: Amber Valletta
Leo reportedly saw Amber in a magazine, asked someone to track her down, and boom — a brief fling was born. Neither of them confirmed it, but the story became classic Leo lore.
1997: Helena Christensen
Another supermodel, another rumor. The gossip was fueled more by the media than facts, so this one is filed under “tabloid speculation.”
1998: Eva Herzigová
Eva actually talked about Leo publicly, calling him kind and full of energy — not-so-subtly hinting their connection wasn’t just platonic. It fizzled quickly, but this fling had a little more substance than the usual whispers.
2000: Virginie LeDoyen
Co-stars in The Beach, Leo and Virginie were rumored to be more than just colleagues. She later brushed it off as exaggerated and admitted she couldn’t imagine living with his level of fame.
2000–2005: Gisele Bündchen
The five-year romance with Gisele was Leo’s first true long-term relationship. They were the definition of a power couple. In her memoir, Gisele revealed that she evolved personally while Leo stayed the same, so she moved on. Still, she credited the relationship for teaching her a lot.
2005–2010: Bar Refaeli
Enter Bar Refaeli. Their on-again, off-again relationship stretched for about five years. The pressure to settle down reportedly contributed to the split — Leo wasn’t ready for marriage.
2011: Blake Lively
In a rare departure from the model trend, Leo briefly dated actress Blake Lively. It began in Cannes and ended within months, blamed on “distance and timing.” Blake quickly found her forever love with Ryan Reynolds.
2012: Erin Heatherton
For almost a year, Leo and Victoria’s Secret model Erin Heatherton were picture-perfect. Their breakup was clean and drama-free — a rarity in Hollywood.
2013: Toni Garrn
Leo’s low-key romance with German model Toni Garrn ended in 2014, with tabloids buzzing after he left a Miami nightclub surrounded by 20 women. The timing didn’t help.
2016: Kelly Rohrbach
The Sports Illustrated model gave us some of the most iconic paparazzi shots: the pair biking through New York City like a rom-com come alive. It didn’t last, but they reportedly stayed on friendly terms.
2016–2017: Nina Agdal
Danish model Nina Agdal dated Leo for about a year, complete with beach vacations and paparazzi moments. The breakup was labeled “amicable.” (Leo’s favorite word, apparently.)
2017–2022: Camila Morrone
This was Leo’s most serious relationship in years. Camila and Leo lasted almost five years, fueling engagement rumors. She openly addressed their 23-year age gap, urging people to focus on their bond instead of the math. But when she turned 25 in 2022, the internet’s “rule” jokes returned with a vengeance.
2022: Victoria Lamas
Leo was linked to actress Victoria Lamas, whose father bluntly told her to enjoy it like a holiday romance. His advice turned out to be accurate.
2022: Eden Polani (Rumored)
Spotted next to 19-year-old Eden Polani at a party, Leo instantly sparked headlines. Sources denied they were dating, but the optics fueled his “forever young” reputation.
2022–2023: Gigi Hadid
This one surprised people. Leo and Gigi were spotted multiple times, hinting at something more than casual, but by early 2023 it fizzled. Still, it was a notable break from his usual “model under 25” pattern.
2023–Present: Vittoria Ceretti
Finally, the Italian supermodel Vittoria Ceretti. They met at Cannes in 2023, and their whirlwind romance escalated quickly with vacations, dates, and public outings. By late 2023, they were reportedly exclusive — and as of 2025, they’re still going strong. Vittoria has even said love with Leo makes her feel secure, suggesting this could actually be the real deal.
The Verdict
Leonardo DiCaprio’s love life has been a saga of supermodels, short flings, and a meme that refuses to die. For decades, he’s been Hollywood’s Peter Pan, dating younger women while avoiding long-term commitment. But with Vittoria Ceretti, he may finally be rewriting his own script.
Will this be the relationship that breaks the cycle? Only time — and maybe the next Cannes Film Festival — will tell.
