Leonardo DiCaprio’s Dating History: A Timeline of His Romances

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Vittoria Ceretti values the privacy she maintains regarding her personal life, including her relationship with Leonardo DiCaprio, and has stated that there’s nothing more valuable than what remains unknown about an individual. In a conversation with Vogue France, she expressed that keeping a part of one’s life private for oneself and loved ones is a rare luxury in our professions, referring to it as her “secret garden.”

Gossips about their romantic involvement first emerged in August 2023. Although Vittoria did not disclose the specifics of her relationship with the Academy Award winner, she mentioned during the interview that they initially crossed paths in Milan and would rather avoid discussing further details.

Since then, Vittoria, aged 26, and Leo, aged 50, have been seen on several public outings together, such as a walk through New York City with intertwined hands back in October. Despite engagement rumors, TopMob News confirmed in November that the two are not engaged at present.

In essence, fans eagerly grab any hints about their relationship dynamics, and Vittoria recently provided a few peeks into her connection with Leo. To start off, it’s obvious that she has watched Titanic, stating in an interview with Vogue France, “Who hasn’t seen it? Or didn’t enjoy it?” She considered it an iconic film. Moreover, it seems that Vittoria has had the chance to meet Leo’s mother, Irmelin Indenbirken, whom she mentioned going through “childhood photos with my boyfriend’s mom.” Lastly, Vittoria has left no doubt about her feelings regarding media labeling her as “Leo’s girlfriend”.

When you start dating someone who has a greater fanbase than you, you often find yourself referred to as ‘the girlfriend/boyfriend.’ This can be quite frustrating,” she noted. “Suddenly, conversations revolve around ‘so-and-so’s girlfriend who used to be so-and-so’s ex.’ It’s disheartening to feel that your love for someone is limited because of the labels society insists on attaching to you.

Despite the constant media focus on her personal life, she makes an effort not to let it overwhelm her.

In a similar vein, Leo has grown accustomed to the countless news articles about his romantic affairs over the years. As he once said in an interview with Extra back in 2013, “Becoming an actor means your private life becomes public, but it’s also a choice you make.” Adapting to these circumstances is something he’s learned to do.

When asked about potential marriage and children in the future, Leo remains open-minded. “I take things as they come,” he said. “Time will tell what happens.”

Moreover, Leo doesn’t try to foresee the future. Instead, he takes it one day at a time.

For those interested in exploring Leo’s past relationships, there’s more information available below.

It’s been said that the first model Leo was romantically linked to was none other than Bridget Hall, a Victoria’s Secret model. The duo were spotted at various events together in 1994. However, her representative at the time dismissed any speculation about them being anything more than friends, stating, “I recall him. He was quite a pesky character. They were just friends; this claim is absolutely false.

At the 1996 premiere of “Romeo + Juliet,” Leo was seen walking hand-in-hand with actress Kristen Zang, a relationship that lasted for two years until their separation in 1998. Despite seldom attending red carpet events with his romantic partners, this was an exception to the rule.

Back in 1998, during the peak of Leonardo DiCaprio’s popularity following the release of “Titanic,” there were whispers suggesting a romantic involvement with Vanessa Trump. Nevertheless, his publicist, Cindy Guagenti, categorically denied these rumors and stated to New York Magazine that year, “He never went out with her.

In 2005, Vanessa tied the knot with Donald Trump Jr., and they subsequently had five children: Kai, Donald, Tristan, Spencer, and Chloe. However, in 2018, the pair decided to separate and filed for divorce, which became official the following year. In March 2025, Vanessa made it public that she is in a relationship with Tiger Woods.

In terms of their commitment, it appears quite significant as Gisele Bündchen is the only woman Leo has accompanied on the red carpet at the Oscars.

Leo and Gisele had an on-again, off-again relationship from 1999 to 2005, making them one of Hollywood’s most secretive power couples. However, in 2005, the famous Brazilian model chose to end things. Later in 2019, she shared publicly about the split, admitting that she was battling panic attacks and felt compelled to alter her lifestyle.

2019 saw her pondering to Porter, “I stopped masking my feelings with cigarettes, alcohol, and overwork, and as a result, I began to notice things I’d previously ignored. Was it just me who yearned for introspection while he remained unchanged? Regrettably, it turned out that I was indeed alone in this.

Eventually, everything fell into place for Gisele. In the year 2009, she tied the knot with Tom Brady, thereby stepping into the role of mother to his son Jack, who was born from a previous relationship with Bridget Moynahan. Over time, they also had children named Benjamin and Vivian together. However, their union ended in 2022.

Gisele has since found new love and welcomed her first child with Joaquim Valente in the year 2025.

Meanwhile, Leo embarked on another serious relationship…

In the year 2006, Leo started dating Sports Illustrated swimsuit model Bar Refaeli, who was 11 years younger than him. (This sentence is easier to read and more natural.)

In 2009, the duo separated for a period of six months, and later Bar expressed her gratitude for that time, stating it as “a half year” to the magazine L’Ish’a. She shared that she utilized this time to gain self-awareness, saying “I came to understand a lot about myself.” Essentially, she worked on herself and matured during this period. Moreover, Bar admitted that prior to this separation, she was unacquainted with the concept of solitude. However, today she understands that a successful relationship requires the ability to be alone without fear. In 2010, there were rumors of their engagement, but these were denied by a source to TopMob News. Eventually, in mid-2011, the couple parted ways permanently.

In May 2011, photographs emerged showing Hollywood’s top actor and the reigning TV sweetheart, Blake Lively, appearing affectionate on a yacht in Cannes.

Indeed, before Blake Lively tied the knot with Ryan Reynolds, she was linked to Leonardo DiCaprio.

Their relationship became public knowledge following their appearance at a glamorous film festival, several months after they were reported to have first met. The Gossip Girl actress, aged 24 at the time, and Leo, who was 36, were later photographed on various dates and showing public displays of affection in Italy, New York, and Australia.

Regrettably, their romance, which had been dubbed the ‘hottest couple’ of summer 2011, came to an end after only five months, with a source confirming to TopMob News that the split was friendly.

In early 2012, after a swift romance with Blake, Leo started dating model Erin Heatherton. They were spotted zip-lining in Mexico alongside his mother, Irmelin, but their relationship didn’t last until November.

In 2013, Leonardo DiCaprio was seen with model Toni Garrn for the first time. They were captured locking lips aboard a yacht in Ibiza. An interesting tidbit: It was during this vacation that Leo attempted flyboarding, an event that later became quite notorious.

By the year 2014, the pair had indulged in luxurious holidays in destinations such as Bora Bora, the French Alps, and St. Barts. Moreover, the German model graced a Golden Globes after-party alongside the famous actor. In an interview with GQ, a 22-year-old Toni expressed her desire to start a family in the future, though she did not mention Leo specifically: “I’ve always dreamed of having four children. However, we’ll have to wait and see. We might begin with one at some point, I guess.

But after 18 months, it was confirmed the pair had split in December 2014. 

In 2017, there were reports suggesting that they reignited their relationship for a short while in New York City. However, it didn’t last and they each moved forward independently. Toni was married to the actor Alex Pettyfer (from Magic Mike), with whom she has daughter Luca, from 2020 until 2023. The subsequent year, there were whispers of a romantic connection between her and Joshua Phitoussi.

In the year 2015, Leo was romantically linked to both a Victoria’s Secret model and a star from “Baywatch”, namely Kelly Rohrbach. However, their relationship didn’t last beyond 18 months as they decided to part ways.

At the specified moment, a source shared with TopMob News that this period is exceptionally hectic for both individuals. Due to their overwhelming schedules, maintaining a relationship proved challenging for them. Despite the complications, they remain good friends and appreciate spending time together.

A wave of excitement swept across the Internet as images surfaced of Leo and Rihanna appearing quite intimate at Coachella in 2016. Remarkably, these snaps emerged only a year following rumors that hinted at their sharing a kiss at a party held at the Playboy Mansion.

It was reported that the singer known as the “Umbrella” artist and the famous actor from the movie Titanic were seen together again at Coachella’s Neon Carnival, which sparked plenty of speculation. However, a source stated in 2016 that they are simply friends who occasionally meet up. They share similar musical tastes, which often brings them together, but neither of them is seeking a romantic relationship at this time.

From as early as 2014, rumors circulated about Leo being connected to Nina Agdal, especially after they were both spotted at the same Super Bowl gathering. However, Nina dismissed these speculations by stating that she hadn’t met him personally, but she had a friend who was invited for dinner with him. She added, “It’s just the kind of social circle you move in, meeting people at parties, so it’s only natural.”

Fast forward to May 2016, Nina and Leo were confirmed to be dating, as a source mentioned they shared great chemistry and often laughed together. Their relationship lasted for about a year, featuring getaways to the Bahamas and Montauk. Unfortunately, their romance came to an end in May 2017.

However, it was discovered that Leo had been preparing to take their relationship a step further when he began dating Camila Morrone in April 2018. They were even seen showing affection towards each other at Coachella that year, although they were first noticed together back in December 2017.

In November 2018, Leo’s relationship with his Daisy Jones & The Six actress partner initially began casually, according to TopMob News sources. However, it later evolved into something deeper and intense. They’ve been almost inseparable for a year and are deeply fond of each other. They have become acquainted with each other’s families and enjoy spending time together.

During the promotion of his 2019 film Once Upon a Time…in Hollywood, Leo found support from Camila at various events. In return, he was by her side as her Instagram companion during their Cannes appearances.

When asked about being labeled an ‘Instagram Boyfriend’ by a meme, Camila responded to Vanity Fair, “He’s an environmentalist and a movie star, but that doesn’t mean anything.”

Unfortunately, after nearly four years together, the duo parted ways in 2022.

It was mentioned in August 2022 that distance influenced the relationship, and it’s said they had grown apart. Nevertheless, their feelings persisted. In July 2024, news broke out that Camila was involved with music video director Cole Bennett.

Following his separation from Camila, there were whispers of a romantic connection between Leo and Gigi Hadid towards the end of 2022. However, a confidant close to him confirmed to TopMob News that in September, the actor from “The Revenant” was relishing his single life and that their relationship with the model was not exclusive. Interestingly, an informant mentioned that Gigi, who is a mother to daughter Khai with her former partner Zayn Malik, shared a similar sentiment. According to a source close to her, she and Leo have been having a great time together recently, trying to keep things low-key and private, and she has been enjoying their quality time.

Over the following months, they frequently appeared in news headlines due to their numerous dinner dates in New York and Italy. Moreover, they graced high-profile events such as a pre-Oscars bash and a Met Gala soiree in 2023’s spring season. Interestingly, both were seen at the same London restaurant where Leo was with his family that June.

However, their relationship didn’t last too long beyond this point. Leo ignited rumors of a new romance with Vittoria Ceretti in August 2023, while Gigi eventually started dating Bradley Cooper.

Leo and Vittoria Ceretti ignited speculations about their relationship back in August 2023, and since then, they have managed to keep most of their intimacy under wraps, appearing only sporadically in public.

In an interview with Vogue France published on March 24, the model shared her thoughts, saying, “The one thing I’ve learned is that what remains unknown about you is the most valuable.” She continued, “Maintaining a private space for yourself and your loved ones is a rare luxury in our professions. So I hold dear my secret sanctuary.”

Despite the constant public scrutiny, Vittoria admitted to trying her best to stay unfazed by it all. In her words, “If what you feel is genuine, if you know that love is there, then there’s no reason to worry.” She concluded, “Love shields and instills confidence.

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2025-03-26 00:47