The romance between reality television mogul Kylie Jenner and Academy Award-nominated actor Timothée Chalamet has evolved from Hollywood’s most unexpected pairing to one of its most serious relationships. What began as whispered rumors in early 2023 has blossomed into a committed partnership that has captured public attention and defied initial skepticism from fans and media alike.
The 27-year-old cosmetics entrepreneur and the 29-year-old Dune star have navigated their relationship largely away from the spotlight, choosing intimate moments over public displays. However, their recent red carpet debut at the 2025 David di Donatello Awards in May marked a significant milestone, signaling their readiness to share their love story with the world.
Their journey together represents more than just another celebrity romance. For Jenner, who previously had an on-and-off relationship with rapper Travis Scott and shares two children with him, this relationship offers something distinctly different. Sources close to the couple describe Chalamet as bringing a calming influence to Jenner’s life, helping her feel “calm and confident” in ways that differ from her past relationships.
The couple’s commitment has deepened considerably, with reports indicating they are “practically living together” as Chalamet frequently stays at Jenner’s home when not working. This integration into each other’s daily lives, combined with family approval from both sides, suggests a relationship built on genuine connection rather than mere Hollywood glamour.
The Beginning: From Fashion Week to Secret Dates
Timothée Chalamet and Kylie Jenner (Image via Getty)
The love story between Jenner and Chalamet traces back to January 2023, when they first met at Paris Fashion Week during the Jean Paul Gaultier show. This initial encounter occurred shortly after Jenner’s split from Travis Scott, with whom she had maintained an on-and-off relationship while co-parenting their children, Stormi and Aire.
Romance rumors began circulating in April 2023 when gossip accounts started posting about the alleged couple. The speculation intensified when Jenner’s distinctive black Range Rover was photographed outside Chalamet’s Beverly Hills home. Paparazzi also captured moments of their early courtship, including a low-key date at Tito’s Tacos in Santa Monica, where they reportedly ate in the back seat of Jenner’s car to maintain privacy.
During these early months, sources described their connection as casual but promising. An insider told Entertainment Tonight that while things weren’t serious initially, Jenner was “enjoying hanging out with Timothée and seeing where it goes,” noting that “it feels a lot different than her past relationships.”
Public Appearances and Growing Commitment
The couple’s first major public appearance together came in September 2023 at a Beyoncé concert, followed by their attendance at the US Open. These outings marked their transition from secret dating to a more open acknowledgment of their relationship.
Their red carpet debut at the 2025 David di Donatello Awards represented a pivotal moment in their relationship timeline. Lip reader analysis revealed Jenner’s initial nervousness, saying “I’m coming…maybe…it’s scary” as she followed Chalamet onto the carpet. When she became overwhelmed and started to walk away, Chalamet’s supportive response of “don’t go, hold on, that was great, come here” demonstrated the caring dynamic between them.
The significance of this public debut cannot be understated. A source explained that “Kylie’s really happy and relieved they finally made their debut. It was time and she wanted to publicly support him and show how proud of him she is.” This moment represented not just a photo opportunity but a declaration of their serious commitment to each other.
Family Integration and Future Plans
Timothée Chalamet and Kylie Jenner (Image via Getty)
One of the most telling aspects of their relationship is the level of family integration achieved by both partners. Chalamet has developed a close relationship with Jenner’s children, with sources noting that “he feels lucky to be able to share a bond with them and is also respectful of her co-parenting relationship with Travis.”
The approval extends to both families, with Chalamet’s mother, Nicole Flender, publicly commenting on Jenner in a recent interview, stating, “I have to say she’s lovely. She’s very nice to me.” This family acceptance is particularly significant given the high-profile nature of both their careers and the scrutiny that comes with their relationship.
Regarding future plans, sources indicate that while the couple isn’t rushing toward marriage, they aren’t ruling it out either. An Entertainment Tonight insider revealed that they “don’t put pressure on their relationship, but everything is going really well, and they could see themselves taking things to the next level someday.”
Challenges and Public Scrutiny
The relationship hasn’t been without its challenges. The couple faced a particularly intense period during awards season early in 2025, with sources noting that “with the awards season and premieres, earlier this year was intense for their relationship.” However, they successfully navigated these pressures, with Jenner consistently showing up to support Chalamet’s career milestones.
Public scrutiny has also been a constant factor, with some fans and body language experts questioning the authenticity of their connection. Despite this skepticism, the couple has maintained their commitment to each other while keeping much of their relationship private.
Their approach to handling fame differs significantly from typical Hollywood couples. They prefer “low-key date nights” and work to “keep their relationship under the radar in order to feel some sense of normalcy.” This strategy has allowed them to build a genuine connection away from constant media attention.
Current Status and What’s Next
Timothée Chalamet and Kylie Jenner (Image via Getty)
As of June 2025, Jenner and Chalamet’s relationship appears stronger than ever. They are “practically living together,” with Chalamet being “fully integrated into her life.” Recent public appearances, including Broadway shows and sporting events, demonstrate their comfort as a couple in various settings.
The relationship represents a significant evolution for both individuals. For Jenner, it offers stability and emotional growth, with sources noting that Chalamet “makes her feel calm and confident, and it is a different relationship from what she has had in the past.” For Chalamet, the relationship provides grounding and support as he navigates his rising Hollywood career.
Their story continues to unfold as one of Hollywood’s most intriguing romances, proving that unexpected pairings can sometimes create the most meaningful connections. With family support, shared values, and genuine affection clearly evident, Kylie Jenner and Timothée Chalamet have built something substantial that extends far beyond the typical celebrity relationship narrative.
Emily Ratajkowski’s dating life has become a constant source of fascination for fans and media alike, particularly following her high-profile divorce from Sebastian Bear-McClard in 2022. The supermodel, actress, and author has been refreshingly open about the dating world as a newly single mother, embracing what she calls her first real experience with dating independence. Her romantic timeline reads like a who’s who of Hollywood and music industry elite, with connections ranging from comedians to pop superstars.
The most talked-about chapter in Ratajkowski’s recent dating history involves none other than Harry Styles, the former One Direction member whose own romantic life regularly makes headlines. Their connection sparked intense media scrutiny when paparazzi captured them in an intimate moment on the streets of Tokyo in March 2023, creating a viral sensation that dominated social media for weeks. What makes this particular romance especially intriguing is how it represents Ratajkowski’s evolution from someone who described herself as a “pick-me girl” to a confident woman who knows exactly what she wants in a partner.
Since her divorce, Ratajkowski has been linked with several high-profile figures, including Pete Davidson, Eric André, and most recently, country-rap artist Shaboozey. Each connection offers insight into her changing perspective on relationships and her journey toward emotional independence. Her openness about this process has resonated with many women in similar life transitions, making her dating experiences both relatable and aspirational.
The Harry Styles Connection: A Tokyo Romance
Emily Ratajkowski and Harry Styles (Image via Getty)
The relationship between Emily Ratajkowski and Harry Styles first came to public attention in March 2023, when photographers captured them kissing on a Tokyo street following one of Styles’ concerts. The images quickly went viral, sparking intense speculation about the nature of their relationship and its timeline. What initially appeared to be a spontaneous encounter was later revealed to have deeper roots.
In a March 2023 podcast interview, recorded weeks before the Tokyo photos surfaced, Ratajkowski hinted at a new romantic interest, saying, “I just started dating someone that I think I like, so that is different. I was like, ‘He’s kind of great’”. This timeline suggests their connection began in early February 2023, making their relationship approximately two months old when the public photos emerged.
Ratajkowski later addressed the viral moment in an interview with Spanish Vogue, expressing her surprise at the intense public reaction. “It’s very bizarre to have certain experiences and then have the whole world know about them and comment on them,” she explained, noting that the attention focused on “a tiny slice of my life” while most of her energy remained devoted to her son and career.
The model also addressed rumors of tension with Olivia Wilde, Styles’ previous long-term partner, firmly dismissing any suggestion of conflict. “I feel bad for Olivia because she has had to suffer this situation on several occasions,” Ratajkowski stated, showing solidarity with Wilde rather than engaging in manufactured drama.
Post-Divorce Dating Evolution
Emily Ratajkowski’s approach to dating has undergone a significant transformation since her divorce from Sebastian Bear-McClard in September 2022. The couple, who married in 2018 and share a son named Sylvester Apollo, ended their four-year marriage amid reports of infidelity. This experience fundamentally changed how Ratajkowski views relationships and her own worth within them.
“I can tell you that I have never been single before,” Ratajkowski revealed in a candid interview. She described experiencing the full spectrum of emotions – anger, sadness, excitement, joy, and levity – as she navigated her first real period of independence. This emotional journey has been both challenging and liberating, allowing her to discover preferences she never knew she had.
The model admitted to previously being a “pick-me girl” who “wasn’t very good at deciding what I liked”. She explained how she used to focus entirely on how potential partners perceived her rather than evaluating her own feelings about them. “I really wanted to be chosen,” she reflected, describing how this mindset affected her self-worth and decision-making in relationships.
Now, Ratajkowski approaches dating with a completely different mindset. “I don’t have that anymore. So now it’s really fun to go to dinner with someone and be like, ‘Cool. I really enjoyed these parts of them. I really didn’t like these other parts,’” she explained. This shift represents a fundamental change in how she values herself and what she seeks in romantic partnerships.
Recent Romantic Connections
Harry Styles and Emily Ratajkowski (Image via Getty)
Beyond her connection with Harry Styles, Emily Ratajkowski has been linked with several other notable figures since her divorce. Her dating history includes comedian Pete Davidson, known for his own high-profile relationships, and comedian-actor Eric André. These connections demonstrate her willingness to explore different types of personalities and relationship dynamics.
Most recently, in August 2024, Ratajkowski sparked rumors with country-rap artist Shaboozey. The pair were spotted together multiple times throughout the month, including at nightclub outings and the premiere of Zoë Kravitz’s film “Blink Twice”. Sources described their connection as “very casual and nothing serious,” with the pair “hanging out and seeing where things go”.
The Shaboozey connection illustrates Ratajkowski’s current approach to dating – exploratory and pressure-free. Rather than rushing into serious commitments, she appears to be taking time to understand what she truly wants in a partner. This measured approach reflects her growth and self-awareness since her divorce.
In a 2024 interview, Ratajkowski discussed how “decentralizing men has been a huge part of my life”. She explained that while she still loves men, she no longer finds the traditional narrative of “being chosen and building a life while being desirable to one man” particularly interesting. This perspective shift has opened up significant space in her life for personal growth and exploration.
Looking Forward: Independence and Growth
Emily Ratajkowski (Image via Getty)
Emily Ratajkowski’s dating journey represents more than celebrity gossip – it’s a public exploration of personal growth and self-discovery. Her willingness to share her experiences openly has created meaningful conversations about modern relationships, divorce recovery, and single motherhood. Through her various romantic connections, from Harry Styles to Shaboozey, she’s demonstrated that dating after divorce can be both healing and empowering.
The model’s emphasis on independence and self-knowledge serves as an inspiration for others in similar life transitions. Her story shows that it’s possible to maintain successful careers, raise children, and explore new relationships while prioritizing personal growth and emotional health.
