Leo's List of Lovers Revealed: 48 Women Named in DiCaprio's Secret Conga Line of Hook-Ups!

Leonardo DiCaprio's dating spree started in 1994 with Bridget Hall. According to People, they were spotted canoodling around New York, but the actor reportedly dumped her after she found their "night of love" disappointing.

Hall clarified the reports and told New York Magazine that The London Sun's 1998 gossip was untrue and that nothing happened between them.

DiCaprio immediately moved on with his The Basketball Diaries costar Brittany Daniel after his split from Hall. Per The Sun, they dated off-screen but never addressed their romance.

Naomi Campbell and DiCaprio are currently good friends, but they had a brief fling in 1995 ahead of the release of his hit film Titanic.

The Parenthood actor sparked dating rumors with Kidada Jones in 1999 after her engagement with Tupac Shakur ended following the rapper's tragic murder.

DiCaprio and Claire Danes followed their Romeo + Juliet characters' love story and had a real-life fling.

The actress revealed in her interview with W Magazine that her romantic interest in the actor was problematic.

"I couldn't really have a crush on the guy I was professionally having a crush on!" she said. "Quite a few gay men have talked to me about the fact that when they were kids watching Romeo + Juliet, they were confused about who they wanted to kiss. It was all about Leo! And I completely understand."

DiCaprio chose Helena Christensen as the woman to hook up with around Titanic's release.

Demi Moore reportedly hooked up with DiCaprio in 1997 as her marriage to Bruce Willis started to hit rock bottom. They were spotted having a dinner amid her marriage troubles.

Due to Titanic's success, more women got linked to the DiCaprio – including Donald Trump Jr.'s ex-wife Vanessa Trump.

New York Magazine published a report about their outing in a New York City nightclub, but DiCaprio's representative dismissed the rumors. Eventually, news outlets exposed her as the one who fed the story to a gossip writer and claimed DiCaprio was happy he was with someone who was so down to earth.

In 1997, DiCaprio reportedly had another brief fling with one of his party friends Natasha Henstridge.

A tabloid claimed that DiCaprio started pursuing Amber Valletta after seeing her in a magazine. He reportedly asked his representatives to track her down and connect him with her.

Bijou Phillips dated DiCaprio in 1998, and DiCaprio played a huge role in connecting her with Hollywood director James Toback, who soon cast her in the film Black and White.

Aerosmith frontman Steven Tyler's daughter Liv Tyler ignited romance rumors with the This Boy's Life actor after photos of them at a late '90s party spread.

Czech supermodel Eva Herzigová stole DiCaprio's heart when they met at the Man in the Iron Mask premiere in 1998, and they had a two-month affair while she was married to Bon Jovi drummer Tico Torres.

The Catch Me If You Can star finally had a long relationship when he met and dated Gisele Bündchen. Their relationship lasted only five years until 2005.

In her interview with Vanity Fair in 2009, she revealed they were not meant to be boyfriend and girlfriend.

DiCaprio had another lengthy romance with Victoria's Secret model Bar Refaeli from 2005 to 2011, though their relationship was on-again, off-again over the years.

Swimsuit model Anne Vyalitsyna met DiCaprio in Ibiza when he broke up with Refaeli. News outlets caught them getting close while enjoying a trip on a yacht in 2009.

Another yacht love story: DiCaprio's romance with Blake Lively started in 2011 while they sailed in the south of France. Their relationship lasted only five months, and they ultimately moved on from their failed fling.

DiCaprio also had a brief romance with American socialite Paris Hilton from September 2000 to November 2000.

In 2012, Erin Heatherton and DiCaprio dated for ten months and broke up because of their schedules.

The Gardener of Eden actor added a young model to his relationship history as they sparked romance rumors in 2013. DiCaprio reportedly asked Jonah Hill for her number, and he soon invited her to his New Year's yacht party in Australia.

DiCaprio and Miranda Kerr became close when they hung out in 2013. At that time, the model had just split from Orlando Bloom.

Toni Garrn broke DiCaprio's dating spree with young models in 2013. They marked one of their first outings as a couple at the 66th Cannes Festival but broke up the following year.

Dating rumors between DiCaprio and Rihanna began in February 2015, but the singer denied it. The rumors resurfaced in January 2016 when the public spotted them having a flirtatious night in a Paris club.

In 2016, DiCaprio and Kelly Rohrbach called it quits after dating for months. h

"They both have intense work schedules and a lot going on in their lives right now," a source told Us Weekly. "They are still friends and talking but it's over."

DiCaprio was spotted with another model in 2016.

Roxy Horner grabbed dinner with the star in New York City.

A source told People that the model was attached to DiCaprio and that they were affectionate. However, the romance rumors ended after she revealed in since-deleted tweets that they were just friends.

Another model appeared on DiCaprio's dating list: Chelsey Weimar.

Page Six cited sources who claimed they saw the duo leaving Nobu Malibu together and that Weimar went to his Los Angeles home based on the photos she shared on Instagram.

Another insider dismissed the rumor and said the report about their relationship was not true.

"He isn't spending time with anyone," said the source. "Most of his time lately has been in places like Indonesia, trying to help save the ecosystem."

DiCaprio reportedly flirted with Laura Whitmore after they met at the 2016 BAFTAs following an after-party. One source claimed he invited her to his hotel room.

DiCaprio's flirting stage with Ford model Victoria Lee Robinson seemingly started when they attended Justin Bieber's Purpose tour in 2016. It is unclear how long they were together or if their relationship progressed.

DiCaprio started a new romance with Nina Agdal in the summer of 2016. However, they reportedly split after their brief romance but remained friends.

As soon as DiCaprio called it quits with Agdal, he sparked romance rumors with Ella Ross. The model previously dated Kourtney Kardashian's ex Scott Disick.

DiCaprio had one of his "most serious" connections with Camila Morrone.

The couple was first spotted at Barney's in Los Angeles in December 2017, but their relationship also attracted criticism because of their more than two-decade age gap.

However, the model soon defended their romance in her interview with the Los Angeles Times.

"There's so many relationships in Hollywood — and in the history of the world — where people have large age gaps," she said. "I just think anyone should be able to date who they want to date."

However, they broke up in August 2022 after four years of dating.

In September 2022, Gigi Hadid and DiCaprio sparked dating rumors after being spotted on an outing. Their dates continued until they broke up in February.

"She hasn't seen him for a while. She just decided that she was done with him," a source told People. "They are at very different places in life. She prioritizes being a mom. It was never that serious anyway."

While dating Hadid, DiCaprio had another romance rumor with Victoria Lamas after they grabbed dinner at The Bird Streets Club. They left the restaurant separately but soon got into the Oscar winner's car together.

After DiCaprio's romances with Hadid and Lamas, new relationship rumors emerged after DiCaprio was photographed getting close to Eden Polani at Ebony Riley's music release party.

However, the buzz did not last long.

"Leo and Eden just so happen to have been seated next to each other at the party and were hanging in the same group," a source told E! News. "Just because Leo might be talking to or sitting with a girl doesn't mean he's dating her."

Neelam Gill sparked speculation that she and DiCaprio were an item. Photos taken during their vacation in a yacht and dinner dates surfaced in July, but she clarified on Instagram hours later that she was not the handsome hunk's new flame.

"In fact, I am in a committed relationship with his good friend, and have been for many months now," she said. "The only reason we have been pictured in the same vicinity is because I have been there with my partner."

Maya Jama was with Bertram and DiCaprio when they snuck out of a bar, and she became the subject of her own romance rumors.

She previously responded to other buzz that exploded earlier this year, asking everyone to stop since they were not dating.

"I've been minding my business on holiday & said I wouldn't respond/pay attention to any of the silly stories anymore but you need to stop now," the Love Island host wrote on X, formerly known as Twitter.

Bradley Cooper's ex Irina Shayk sparked rumors she was dating DiCaprio after they mingled at Levi and Don Julio's Neon Carnival event. Their representatives did not clarify their relationship, but they have been longtime friends before the rumors broke.

DiCaprio was spotted canoodling with another young model as of late.

The young beauty, confirmed to be 25-year-old Italian model Vittoria Ceretti, sparked dating rumors with DiCaprio after they were spotted kissing at the Hi Ibiza club in Ibiza, Spain. A source told Daily Mail that the duo has been dating for at least two months now.

"It has obviously led to much chatter within his circle that Leo is ready to hang up his lothario ways," the unnamed insider said. "There have been many women pictured with him, partying with him, but what he has with Vittoria is much more serious."