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
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
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’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.
