Leonardo DiCaprio's Dating History: From Gisele Bündchen to Gigi Hadid

Bridget Hall

Hall has the honor of being the first supermodel connected to the actor. The pair were spotted canoodling in 1994 when they were just teens, but they never confirmed their relationship. Rumors abound that Hall ultimately found the experience "disappointing."

Kristen Zang

Zang, then 22, snagged some time with DiCaprio before he transformed into a megastar upon the release of 1997's Titanic. Not quite star-crossed lovers, this couple did attend the premiere of Romeo + Juliet (1996) together.

Nearly two decades after their romance — which she avoided publicly sharing details about — Zang spoke to PEOPLE in Septembeer 2022 about her past relationship with the actor (and spoke her mind on the "ageist" headlines surrounding his breakup with Camila Morrone).

"It was, dare I say, an innocent time," said Zang. "We were nerds. Good looking nerds with glamorous jobs, but still nerds. We went to amusement parks, concerts, museums and the movies.

Helena Christensen

Titanic served as DiCaprio's ticket to all of Hollywood's glory, including the dating field. The actor allegedly chose Christensen as the first model to take out post-iceberg in 1998, when she was 30. Neither DiCaprio nor Christensen confirmed their relationship.

Amber Valletta

The actor's second fling of 1998 was with model-turned-actress Valletta, who was 24 years old at the time. As the story allegedly goes, DiCaprio spotted the model in a magazine and had his people call hers to arrange a meetup that sparked a brief relationship.

Bijou Phillips

The actor is credited with dating model and actress Phillips in 1998 when she was 18 and jump-starting the starlet's career. He reportedly helped her land one of her first film roles in Black & White (1999) by introducing her to the director, James Toback (who, allegedly, has been accused of being a "serial sexual predator").

Eva Herzigová

DiCaprio and then-24-year-old supermodel Herzigová were said to have a one month relationship in 1998, but never confirmed the tryst. Maybe that's because Herzigová was married to Bon Jovi's drummer Tico Torres throughout the alleged affair.

Gisele Bündchen

Before Bündchen started dating (and later married) NFL superstar Tom Brady, the then-20-year-old supermodel was in a serious relationship with the actor from 2000 to 2005. She was even his date to the 2005 Oscars, where he was nominated for Best Actor for The Aviator. It marked the first and only time he'd ever brought a girlfriend as his date to the ceremony.

The couple would go on to have several on-again-off-again moments, but they eventually called it quits almost six years after they were first linked romantically.

"We were very young, and we grew together in a lot of ways," Bündchen said in a March 2009 interview with Vanity Fair. "We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best."

Bar Refaeli

Israeli model Refaeli — who was 20 at the time — and DiCaprio's romance might've started as a fling but quickly evolved into a serious relationship. The couple began dating in 2005; though they took a six-month break in 2009, many DiCaprio trackers thought the pair would settle down after reconciling. However, they split in 2011. Refaeli is now married to Adi Ezra and has three children.

Anne Vyalitsyna

Before she was Adam Levine's ex, the then-23-year-old Russian model (also known as Anne V. in the industry) was connected to DiCaprio in 2009. Some say that she and the actor had a brief romance while DiCaprio was on a break from his relationship with Refaeli.

In 2015, she and then-boyfriend Adam Cahan welcomed daughter Alaska. The two got engaged in 2016 before separating in 2018.

Blake Lively

Lively and DiCaprio romped it up around Europe in 2011 and dated for a few months — while the then-24-year-old actress was shooting Gossip Girl during a brief time when the show was set in L.A.

"When I think about shooting the L.A. episodes, Blake was dating [DiCaprio] at the time, and she had this thing where she had a doll that she took photos of that she sent to Leo," Gossip Girl executive producer Joshua Safran told Vanity Fair in August 2017.

DiCaprio and Lively broke up later that year, and the actress started dating her current husband, Ryan Reynolds, with whom she is expecting her fourth child after welcoming three daughters.

Erin Heatherton

After dating for nearly a year in 2011, the couple had an amicable split, citing the actor's demanding movie projects as the main factor. Despite their breakup, Heatherton, then 22, and DiCaprio remained friendly, with the model calling the actor "a wonderful person" and "a friend of mine" in a 2015 interview with E! News.

Mădălina Ghenea

Photographers spotted DiCaprio entertaining the Romanian model, then 24, during his stay in Australia for The Great Gatsby in 2011. Reports said the rumored relationship lasted a few dinners before fizzling out.

Toni Garrn

DiCaprio and the Victoria's Secret model dated in 2013 when she was 20, making headlines after they were first spotted taking photos together while walking the grounds and gardens of France's Chateau de Versailles together. The pair initially connected at the Cannes Film Festival, where DiCaprio premiered The Great Gatsby that year. They seemingly reconnected briefly in September 2017 when they were seen holding hands while leaving an N.Y.C. nightclub.

However, Garrn moved on to marry another actor, Alex Pettyfer, in October 2020 and welcomed a baby daughter the following year. Garrn and Pettyfer exchanged vows again in June 2022 in Greece.

Rihanna

In 2015, rumors circulated that the singer and actor were casually dating. A source told PEOPLE that although Rihanna and DiCaprio didn't act like a couple during the "Born Again" singer's 27th birthday festivities, they did share a few flirtatious moments.

"They weren't couple-y, but they would flirt and dance, so definitely a little magic there," said the onlooker. "They were definitely flirty and dancing, but not over the top."

Kelly Rohrbach

DiCaprio and Sports Illustrated model Rohrbach, then 24, began dating in the summer of 2015, and they were spotted riding around N.Y.C. on Citi bikes that June. The couple was never shy about showing some PDA — they were often seen kissing and holding hands while on outings. After a few months together, the actor and model called it quits, with a source telling PEOPLE that scheduling conflicts led to their breakup.

"They are very friendly, and it's super amicable," an insider close to the pair shared in January 2016. "They are both so busy, and he's got a big movie coming out, and she's one of the biggest supermodels in the world. There is no other person in the picture."

Roxy Horner

In April 2016, the actor was spotted getting cozy with the model when they stepped out to grab dinner in N.Y.C. alongside DiCaprio's close friend Lukas Haas and another blonde.

"She was very attached to Leo," a source told PEOPLE of Horner. "She was definitely with him, she was holding onto his arm. They were affectionate."

Despite the evident PDA, the model addressed romance rumors in a series of now-deleted tweets. "You can't have a friend in the industry without people assuming it's more than that it's a joke," she wrote. In a second tweet, she assured fans that she did not go home with DiCaprio. "FYI, we all went our separate ways home, as friends do."

Nina Agdal

DiCaprio and Agdal, then 24, dated for a year after first being spotted at a New York City club in May 2016. Following their split, a source close to the actor told PEOPLE that he wasn't ready to take the next step.

"Leo thought Nina was a super cool girl," said the source. "It almost seemed different this time because he was way more affectionate and public with her than he normally is, but his friends knew it wouldn't last."

The source added, "He's not ready to settle down and just isn't in the mindset to get married or have kids."

Ela Kawalec

Before leaving for Cannes, DiCaprio took advantage of the beautiful spring weather in May 2016 by going on a bike ride around N.Y.C. with the Polish model, then 21. The night before their bike ride, the pair went to dinner together and attended a birthday celebration at N.Y.C. nightclub Marquee, where they appeared "couple-y."

An eyewitness told Page Six the pair kept close the whole night: "They were dancing. Leo was dancing with her in his arms and canoodling. They were doing their thing, bumping and grinding."

Georgia Fowler

After a long day of movie premieres and exclusive events at the Cannes Film Festival in May 2016, the actor decided to let off some steam as he partied the night away at Gotha Club with the then-24-year-old Victoria's Secret model. At one point, Fowler wrapped her arm around DiCaprio, pulling him closer to her while they danced together. Fowler has since moved on, welcoming daughter Dylan Aman with boyfriend Nathan Dalah in September 2021.

Lorena Rae

In September 2017, DiCaprio was spotted spending quality time with the then-23-year-old German model at New York City's MoMA PS1. They continued their outing with a dinner date at Hillstone restaurant, according to Page Six. Although the actor's rep said they were not dating, Rae was seen among a group of revelers soaking up the sun on a yacht in St. Tropez with DiCaprio and his pal Tobey Maguire earlier that summer in May 2017 following his split from Agdal. However, the two fizzled out by the end of that fall.

Camila Morrone

Following a holiday vacation in snowy Colorado, the Oscar winner was spotted stepping off a private jet in Los Angeles with the then-20-year-old model. DiCaprio was first linked with Morrone in mid-December 2017 when he was seen leaving her house. Morrone joined the festivities in Colorado along with DiCaprio's close friend Maguire and his two kids — Otis Tobias and Ruby Sweetheart.

"They are family friends, and the two families are very close," a friend of DiCaprio and Morrone told PEOPLE.

On Aug. 30, 2022, PEOPLE confirmed the two had split after nearly four years together.

Gigi Hadid

Hadid and the actor were first spotted together in September 2022. That same month, an entertainment source told PEOPLE that DiCaprio "is taken with Gigi" and that she "is the type of woman he is usually attracted to." According to a film source, the duo "like each other and are having a good time."

Then, in November, the pair continued to see each other.

"Gigi keeps spending time with Leo in N.Y.C.," a source close to Hadid told PEOPLE. "He is very understanding about her being a mom and works around her schedule to see her — it's very sweet. Gigi is smitten."

The insider added that DiCaprio "is a gentleman and quite romantic" but still values keeping "things private" between the pair.

"Gigi shares few details, but she very much enjoys seeing Leo," the source continued.

In February 2023, a source close to Hadid told PEOPLE that the relationship had "fizzled" out.

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

Vittoria Ceretti

DiCaprio and Ceretti have been linked since August 2023, when they were spotted together in Santa Barbara, California.

A month later, the pair were seen locking lips at a club in Ibiza, Spain, and spending time with DiCaprio's mother, Irmelin Indenbirken, in Milan.