Leonardo DiCaprio, the Academy Award-winning actor known for his iconic roles in films like Titanic and The Wolf of Wall Street, has long been a subject of fascination when it comes to his romantic relationships. For decades, the Hollywood star has been linked to numerous high-profile models and actresses, earning him a reputation as one of entertainment’s most eligible bachelors. However, his current relationship with Italian model Vittoria Ceretti appears to be breaking new ground in the actor’s well-documented dating history.
At 50 years old, DiCaprio seems to have found something special with the 26-year-old Ceretti, whom he has been dating since August 2023. Their relationship has captured significant media attention, not just because of DiCaprio’s celebrity status, but also due to the apparent seriousness and longevity of their connection. Unlike many of his previous relationships, this romance has shown remarkable staying power, with the couple making several public appearances together and even attending the prestigious Met Gala as a pair in May 2025.
The relationship represents a notable shift for DiCaprio, who has historically been known for dating younger models and actresses, often ending relationships around the time his partners reach their mid-twenties. With Ceretti, however, there appears to be a different dynamic at play, one that has sparked speculation about potential engagement and a more permanent commitment. As we delve deeper into DiCaprio’s current romance and examine his extensive dating history, we’ll explore what makes this relationship unique and why it might signal a new chapter in the actor’s personal life.
Current Relationship: Leonardo DiCaprio and Vittoria Ceretti
Leonardo DiCaprio and Vittoria Ceretti (Image via Getty)
Leonardo DiCaprio’s relationship with Italian model Vittoria Ceretti began in August 2023 when the pair were first spotted enjoying ice cream together in Santa Barbara, California. The initial sighting marked the beginning of what would become one of DiCaprio’s most enduring and public relationships in recent years.
The Timeline of Their Romance
The couple’s relationship has progressed steadily since their first public appearance. In September 2023, Ceretti was introduced to DiCaprio’s mother, Irmelin Indenbirken, during a museum visit in Milan—a significant step that suggested the relationship was becoming more serious. By March 2024, engagement rumors began circulating when Ceretti was spotted wearing a ring on her left hand, though these speculations were later dismissed.
The relationship reached a new milestone in May 2025 when DiCaprio attended his first Met Gala with Ceretti as his date. While they didn’t walk the red carpet together, their appearance at the prestigious event marked a significant public acknowledgment of their relationship. The couple was photographed together inside the Metropolitan Museum of Art, with Ceretti wearing a pinstripe mini dress by Moncler x EE72 and DiCaprio in a classic black tuxedo.
Ceretti’s Perspective on the Relationship
In March 2025, Ceretti broke her silence about dating DiCaprio in an interview with Vogue France, providing rare insight into their relationship. She expressed frustration with being labeled simply as “Leonardo DiCaprio’s girlfriend,” stating that being in a relationship with someone who has a larger following can be quite irritating as you become known primarily through that association.
Despite the challenges of dating someone in the public eye, Ceretti emphasized the genuine nature of their connection, explaining that if what you’re experiencing is real and you know you love each other, there’s no reason to be alarmed because love protects and gives confidence. She revealed that they first met in Milan, though she preferred to keep further details private.
Recent Engagement Speculation
Recent reports from June 2025 suggest that DiCaprio and Ceretti may be moving toward engagement. Sources close to the actor indicate that their relationship has become increasingly serious, with DiCaprio reportedly ready to change his lifestyle and start a family. This development would mark a significant departure from the actor’s previous pattern of relationships and could signal his readiness for long-term commitment.
Leonardo DiCaprio’s Dating History: A Pattern of High-Profile Relationships
Leonardo DiCaprio (Image via Getty)
Leonardo DiCaprio’s romantic history reads like a who’s who of the modeling and entertainment world, with the actor consistently linked to some of the most beautiful and successful women in fashion and Hollywood.
Early Relationships and Supermodel Era
DiCaprio’s first public relationship was with supermodel Bridget Hall in 1994. This set the tone for what would become a clear pattern: the actor’s preference for dating models, particularly those associated with Victoria’s Secret and Sports Illustrated. Throughout the late 1990s and early 2000s, he was linked to numerous high-profile models including Naomi Campbell, Helena Christensen, and Kristen Zang.
Long-Term Relationships
Two relationships stand out as DiCaprio’s most serious long-term commitments before Ceretti. His relationship with Brazilian supermodel Gisele Bündchen lasted from 2000 to 2005, making it one of his longest relationships. The couple was frequently photographed together, and DiCaprio famously took Bündchen as his date to the Academy Awards.
Following Bündchen, DiCaprio entered another significant relationship with Israeli model Bar Refaeli, which lasted from 2005 to 2011. Their relationship was notably on-and-off, with the couple breaking up in 2009 before reconciling, only to split permanently in 2011. According to reports, neither was ready to take the relationship to the next level, leading to their final breakup.
The “25 Rule” and Recent Relationships
DiCaprio’s dating pattern has become the subject of internet memes and cultural commentary, particularly the observation that he rarely dates women over 25. His most recent long-term relationship before Ceretti was with actress and model Camila Morrone, which lasted four years and ended in August 2022 when Morrone was just over 25.
Other notable relationships include brief romances with actress Blake Lively in 2011, various Victoria’s Secret models including Erin Heatherton and Toni Garrn, and more recent connections with models like Kelly Rohrbach and Nina Agdal.
What Makes the Ceretti Relationship Different
Leonardo DiCaprio and Vittoria Ceretti (Image via Getty)
Several factors distinguish DiCaprio’s relationship with Vittoria Ceretti from his previous romances, suggesting this could be the relationship that breaks his established patterns.
Duration and Stability
At nearly two years, DiCaprio’s relationship with Ceretti has already outlasted many of his previous connections. The consistency and apparent stability of their relationship, without the on-and-off nature that characterized some of his past romances, suggests a more mature approach to commitment.
Age Factor
While Ceretti is currently 26, she was 25 when they began dating, and DiCaprio has continued the relationship well past her 25th birthday—breaking his supposed “rule” about dating women over that age. This shift has been noted by media outlets as potentially significant in understanding DiCaprio’s evolving approach to relationships.
Public Integration
The couple’s appearance at the Met Gala and Ceretti’s introduction to DiCaprio’s mother suggest a level of integration and seriousness that wasn’t always present in his previous relationships. These public acknowledgments indicate DiCaprio’s willingness to be seen as part of a committed couple.
Mutual Respect and Understanding
Kendall Jenner’s dating life has been a rollercoaster of high-profile relationships, breakups, and reconciliations that have kept fans and media outlets guessing for years. As the most private member of the Kardashian-Jenner clan when it comes to romance, the 29-year-old supermodel has managed to maintain an air of mystery around her personal relationships while still generating significant public interest.
Unlike her sisters who often share intimate details of their romantic lives on social media and reality television, Kendall has consistently chosen to keep her relationships largely out of the spotlight. This approach has made every look into her love life all the more intriguing for fans who eagerly follow her romantic journey.
The model’s most notable relationships have included NBA star Devin Booker and Puerto Rican rapper Bad Bunny, both of whom she has dated multiple times in an on-again, off-again pattern that has become characteristic of her romantic history. Her relationship timeline reads like a complex web of reconciliations, breakups, and new beginnings that span several years.
Currently, Kendall’s relationship status appears to be single following her most recent breakup with Devin Booker, though the pair’s history suggests this may not be permanent. Their pattern of reconnecting after periods apart has become a defining feature of their relationship, leaving fans wondering if another reconciliation might be on the horizon.
The Devin Booker Saga: A Five-Year On-and-Off Romance
Kendall Jenner and Devin Booker (Image via Getty)
The Beginning of Their Love Story
Kendall Jenner and Devin Booker’s relationship began in April 2020 when they were first photographed together on a road trip to Sedona, Arizona. The Phoenix Suns player, now 28, initially kept things casual with the model, but their connection proved to have staying power despite numerous obstacles along the way.
The couple didn’t make their relationship Instagram official until Valentine’s Day 2021, when Kendall shared a rare photo of them together on her Instagram Story with a simple white heart emoji. This public acknowledgment was significant given Kendall’s typically private approach to relationships, signaling that their connection had become more serious.
Their Most Recent Reconciliation and Breakup
After rekindling their romance in February 2025, sources confirmed that Kendall and Devin were “very much together” and appeared to be in a solid place. The couple was spotted being affectionate at a friend’s dinner party in New York City and spent Valentine’s Day weekend together in Aspen, Colorado.
However, their latest attempt at love was short-lived. By June 2025, the couple had quietly broken up “over a month ago,” according to sources who cited “communication issues” as the primary reason for their split. The insider explained that their busy schedules and inability to stay “on the same page” ultimately led to another breakup in their tumultuous relationship history.
The Pattern of Breakups and Reconciliations
Kendall and Devin’s relationship has been characterized by multiple breakups and reconciliations over their five-year history. Their first major split occurred in June 2022 after two years together, with sources citing that they were “on different paths.” However, they reconciled briefly before breaking up again in October 2022.
The couple explored dating again in February 2024, though they weren’t exclusive initially. This reconciliation came after Kendall’s relationship with Bad Bunny had ended, and friends reportedly hoped she would reunite with Devin, believing he made her happiest.
The Bad Bunny Interlude: A High-Profile Romance
Kendall Jenner and Bad Bunny (Image via Getty)
Their First Relationship
Between her on-and-off relationship with Devin Booker, Kendall dated Puerto Rican rapper Bad Bunny from February 2023 to December 2023. Their relationship began when they were spotted making out at a private Los Angeles club, and it quickly became a fan favorite pairing.
The couple attended high-profile events together, including the Met Gala, and were frequently photographed on dates throughout 2023. Despite their chemistry, busy schedules, and Bad Bunny’s world tour plans ultimately led to their split in December 2023.
Their Brief 2024 Reunion
Kendall and Bad Bunny rekindled their romance in May 2024 after being spotted together at a Met Gala afterparty. Their reunion was described as passionate, with sources noting their “crazy attraction to each other.” However, this second attempt at love was even shorter-lived than their first, ending by September 2024.
The timeline of Kendall’s relationships during this period was particularly complex, as she was simultaneously exploring a reconciliation with Devin Booker while dating Bad Bunny. This overlap created tension, with sources noting that Bad Bunny “had not been happy” about her reconnecting with Devin.
Kendall’s Dating Philosophy and Approach to Love
Her Commitment to Privacy
Throughout all her relationships, Kendall has maintained her preference for keeping her romantic life private. Sources consistently note that she and her partners “like to keep their relationship private” but are “very touchy-feely when they’re with friends.”
This approach differs significantly from her famous sisters, who often share relationship details publicly. Kendall’s commitment to privacy has made her relationships more mysterious and, arguably, more intriguing to the public.
Her Philosophy on Love and Relationships
In a 2023 interview, Kendall revealed her approach to love, stating, “I love really hard, and I love without apology. I don’t like goodbyes, and I will fight to not have to say goodbye.” She emphasized that she “will always fight for relationships” and doesn’t “give up on anything.”
This philosophy helps explain the pattern of reconciliations in her romantic history, particularly with Devin Booker. Her willingness to give relationships multiple chances has resulted in the complex on-and-off dynamic that has characterized her most significant relationships.
Current Relationship Status and Future Prospects
Kendall Jenner (Image via Getty)
Single and Focusing on Herself
As of June 2025, Kendall Jenner appears to be single following her latest breakup with Devin Booker. Sources suggest that she may be focusing on her career and personal growth during this period, similar to her approach in late 2024 when she expressed wanting to “stay single for now.”
Potential for Future Reconciliations
Given the pattern of her relationship with Devin Booker, fans and media outlets continue to speculate about the possibility of another reconciliation. Their five-year history of breaking up and getting back together suggests that their story may not be over, though only time will tell if they can overcome their communication issues and scheduling conflicts.
Marriage and Family Plans
When asked about marriage plans, Kendall’s mother, Kris Jenne,r stated that the family has “no marriage plans — yet.” However, Kendall has expressed interest in having children someday, mentioning that she would like “three max” but would be “cool with two.” Whether these future plans will include Devin Booker or someone new remains to be seen.
