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.
Ayo Edebiri, the breakout star of FX’s critically acclaimed series “The Bear,” has captured audiences worldwide with her compelling portrayal of Sydney Adamu. As her career continues to soar with Emmy nominations and major film roles, fans are increasingly curious about her personal life, particularly her romantic relationships. The talented actress and comedian has managed to maintain a remarkably private personal life despite her rising fame, leading to widespread speculation about her dating status.
The 28-year-old Boston native has become one of Hollywood’s most sought-after young talents, starring alongside Jeremy Allen White in “The Bear” and lending her voice to major animated films like “Inside Out 2.” Her success has naturally drawn public interest in her off-screen relationships, with fans eagerly dissecting every public appearance and social media post for clues about her romantic life. While Edebiri has consistently chosen to keep her personal relationships away from the spotlight, several confirmed and rumored relationships have emerged over the years.
From her publicly confirmed relationship with actor Colin Burgess to persistent rumors linking her with co-stars Jeremy Allen White and Paul Mescal, Edebiri’s dating history reflects her preference for privacy while the complexities of fame. Recent developments have also connected her to musician Jamen Whitelock, adding another layer to the ongoing speculation. Understanding her relationship timeline provides insight into how this rising star balances personal privacy with public scrutiny in an increasingly connected entertainment.
Colin Burgess: The Confirmed Relationship
Ayo Edebiri (Image via Getty)
The only publicly confirmed romantic relationship in Ayo Edebiri’s dating history involves actor and comedian Colin Burgess. Their relationship became public knowledge through two significant social media moments that offered rare glimpses into Edebiri’s private life.
The couple made their most significant public appearance together at the Emmy Awards in September 2022, where Edebiri served as a first-time presenter. Burgess attended as her date and later shared photos from the event on Instagram with the caption: “Congrats to my gf Ayo on presenting her first Emmy.” This Emmy appearance represented a milestone moment for both Edebiri’s career and their relationship.
Current Status with Burgess
The current status of Edebiri and Burgess’s relationship remains unclear. When fans discovered their relationship in September 2023, some expressed negative reactions, prompting Burgess’s friend, “Fire Island” actor Joel Kim Booster, to defend him on social media. Booster wrote in a since-deleted tweet: “I’ve known Ayo’s boyfriend for close to a decade and he is such a kind, smart, funny dude and y’all are being weird as shit.”
As of 2024, neither Edebiri nor Burgess has provided updates about their relationship status, maintaining their preference for privacy. The lack of recent public appearances or social media posts together has led to speculation about whether they remain together.
Jeremy Allen White: Co-Star Chemistry Sparks Romance Rumors
Ayo Edebiri (Image via Getty)
The most persistent dating rumors surrounding Ayo Edebiri involve her “The Bear” co-star Jeremy Allen White. Their on-screen chemistry as Sydney and Carmy has translated into widespread fan speculation about a potential off-screen romance.
The Chicago Cubs Game Incident
Romance rumors intensified in May 2024 when a video surfaced showing Edebiri and White at a Chicago Cubs game at Wrigley Field alongside other cast members. The footage captured White with his hand on Edebiri’s back, gently rubbing it, which fans interpreted as evidence of a romantic relationship. The intimate gesture sparked widespread discussion on social media platforms.
Vanity Fair Interview Revelations
Both actors addressed their relationship in a May 2024 Vanity Fair cover story featuring Edebiri. White expressed his admiration for his co-star, stating: “We genuinely enjoy each other’s company, both on and off-camera. I hold her in high regard as a person and as an artist.”
Despite the mutual admiration and apparent closeness, both actors have maintained that they are simply close friends and professional collaborators.
Paul Mescal: The St. Patrick’s Day Connection
Ayo Edebiri (Image via Getty)
Another significant rumor linked Edebiri to “All of Us Strangers” co-star Paul Mescal following a March 2024 Instagram story post. The image showed Edebiri holding Mescal’s arm as they shared a laugh in a stairwell, with Edebiri captioning it “Happy St. Paddy’s 🍀.”
The post played into an ongoing internet joke about Edebiri being Irish (she’s not), but fans interpreted the intimate nature of the photo as evidence of a romantic relationship. However, sources close to the situation confirmed to People magazine that the two are “just friends.”
Mescal has expressed interest in working with Edebiri again, telling AwardsWatch in November 2023: “I think in the next five years I’m going to set myself a challenge to do maybe a rom-com with Ayo, or something like that would be cool.” Author Emily Henry even reposted their photo, hinting at a potential collaboration on a rom-com adaptation of her work.
Jamen Whitelock: The Latest Connection
More recent speculation has connected Edebiri to musician Jamen Whitelock. In January 2025, Edebiri shared an Instagram story image showing Whitelock kissing her on the cheek. The pair has been photographed together on multiple occasions, though they have never officially confirmed any romantic involvement.
This potential relationship represents the most current speculation about Edebiri’s dating life, though, like her previous rumored connections, she has chosen not to address it publicly.
Edebiri’s Approach to Privacy
Throughout her rising fame, Ayo Edebiri has consistently maintained strict boundaries around her personal life. She has chosen not to discuss her relationships in interviews or on social media, preferring to let her professional work speak for itself. This approach has only intensified public curiosity about her romantic life.
Her commitment to privacy reflects a broader trend among young celebrities who seek to maintain some separation between their public and private personas. Despite fan speculation and media attention, Edebiri continues to focus primarily on her career achievements and artistic collaborations.
