Harry Styles’ romantic escapades have captured huge attention, from his Swiftie days to his recent public kiss with Emily Ratajkowski in Tokyo. Following his breakup with Olivia Wilde in November 2022—after a rocky period post the infamous Don’t Worry Darling drama—Styles has opted for a more subdued lifestyle away from the spotlight, especially since completing his Love On Tour in July 2023.
Since that time, he has been seen with Emily Ratajkowski, Taylor Russell, and Olivia Dean. However, he has refrained from making any official statements regarding his relationships with any of these women.
Harry Styles and Olivia Dean seen together, but fans believe they’re working on a musical collaboration
Given his status as one of the world’s most eligible bachelors, it’s no surprise that speculation about his love life swirls rapidly. Although Styles has never publicly confirmed a serious relationship, here’s a breakdown of his alleged current and past romantic interests.
Recently, Olivia Dean has been linked to Styles, creating quite a buzz among fans when they were spotted together at a Five Guys in St. Pauls, London. Initial dating rumors emerged from these sightings but have since been dismissed, as they are believed to be good friends possibly collaborating on music—a perfect match for a musical partnership in 2024 and beyond.
At the beginning of September 2023, Styles and Bones and All star Taylor Russell were reported by DeuxMoi to be casually dating but not yet in an exclusive relationship. Nevertheless, a source hinted that things were progressing.
Their connection seemed to be solidified when Styles attended the press night of Russell’s play The Effect at the National Theatre in London. The following day, the pair were seen walking along Brewer Street in London after leaving the Chiltern Firehouse together.
By mid-October, reports indicated that Styles and Russell’s relationship had deepened. A source told US Weekly that Styles “sees a future” with her, expressing that “Harry is head over heels for Taylor” and loves spending as much time with her as possible.
Following the BAFTAs in February 2024, rumors of engagement arose when Russell was spotted wearing a Tiffany & Co. ring, albeit on the incorrect hand. However, by May 2024, speculation suggested they had ended their relationship. A source revealed that after a challenging trip to Tokyo in April, they decided to take a break, noting, “Things have become strained recently.”
Just four months after his split from Wilde, Styles was seen sharing a passionate kiss with model Emily Ratajkowski in Tokyo. This incident reportedly prompted Wilde to sever ties with both Styles and Ratajkowski, who was once a close friend of hers.
Styles’ relationship with Olivia Wilde began in January 2021, and they were first photographed together at his manager Jeffrey Azoff’s wedding. Their romance reportedly blossomed during the filming of Don’t Worry Darling, leading to more public appearances, including a boat trip off the Italian coast and Wilde attending Styles’ concerts.
Despite being “more serious than ever” during the summer of 2022, their relationship reportedly faced difficulties after the chaotic press tour for Don’t Worry Darling. By November 2022, sources confirmed they were “taking a break,” citing their individual commitments—Wilde focusing on her children and career in L.A. while Styles continued his tour.
French model Camille Rowe was rumored to have dated Styles in 2017, but their relationship ended within a year, serving as inspiration for his acclaimed album Fine Line. Styles confirmed that his single “Cherry” features Rowe’s voice at the end, with a voicemail in French translating to a playful conversation.
Following his breakup with Jenner, Styles was rumored to have had a brief relationship with British blogger and chef Tess Ward in 2017, first seen together in London and later at an event in matching shirts. However, by June of that year, reports indicated that Ward had reconciled with her ex-boyfriend.
Styles’ connection with Kendall Jenner began in 2013 after they were spotted on a date at the Los Angeles restaurant Craigs. They spent New Year’s together and later vacationed in the Caribbean. In 2016, Khloé Kardashian confirmed their relationship status in an interview, acknowledging their time spent together in St. Barts.
Although they reportedly split in early 2016, they briefly rekindled their romance later that year, with Styles attending Jenner’s 21st birthday party. In a Rolling Stone interview, Styles admitted that Jenner greatly influenced his debut album, describing her as “a huge part of the album.”
Possibly one of the most talked-about relationships was between Styles and Taylor Swift, which lasted for about a month in late 2012. Their romance started when they were seen together in Central Park and ended after a Caribbean holiday in early 2013. Fans continue to speculate about Swift’s lyrics, with many believing her song “Style” references Styles, highlighted by the lyric about classic red lips and a white T-shirt.
While still in One Direction, Styles allegedly had a brief fling with Inbetweeners actress Emily Atack in 2012. Both neither confirmed nor denied their relationship status during their time together. Years later, Atack remarked that it was “a short-lived thing that was just a bit of fun,” indicating they went their separate ways after a brief and enjoyable encounter.
Harry Styles briefly dated television presenter Caroline Flack in 2011 when he was just 17 and she was 31. Their relationship drew considerable media scrutiny due to the age gap, stemming from their meeting while Flack was hosting The Xtra Factor. The couple’s romance lasted only a couple of months before ending despite intense public attention.
Before rising to fame, Styles dated Felicity Skinner, whom he met through mutual friends as teenagers. In an interview, she recalled him as a romantic and shy boyfriend, describing their relationship as puppy love. Their romance lasted just under a year, and although they have since lost touch, Skinner fondly remembers their time together.
