How Harry Styles is the ultimate rebound guy – from snogging divorcee Emily Ratajkowski to fling with heartbroken singer
IF you’re looking for a holiday from heartbreak, just call Harry Styles.
Over the weekend, the former One Direction singer, 29, was snapped passionately kissing Emily Ratajkowski in Tokyo just six months after she filed for divorce.
The supermodel, 31, split from her husband of four years, Sebastian Bear-McClard, last year following claims that he was unfaithful.
She said in February: “I know a lot of people who are unhappily married for a very long time because they’re so afraid of divorce and I don’t think that’s a good way to live.”
It’s not the first time, however, that prolific dater Harry has ended up with someone fresh out of a relationship.
Here, we examine the evidence that he is the ultimate choice for an A-list rebound.
Taylor Swift
Harry was spotted dating Taylor, 33, just a month after she split from Conor Kennedy, 28 – the son of Robert F. Kennedy.
Insiders had claimed that Taylor, who was 22, freaked the then 18-year-old Conor by coming on too strong – and because of her apparent obsession with his famous family.
Taylor and Harry sparked romance rumours in November 2012 when he attended the rehearsal for her X Factor performance.
“He was smiling at her while she rehearsed. When she was done he jumped up on stage, picked her up, put her over his shoulder and carried her off stage,” a source told People. “The whole crew was really surprised.”
Less than a month later they were spotted on a date in Hyde park and later kissing at a birthday party in New York.
Before they split in 2013, the couple fitted in a Caribbean holiday and a NYE party in New York.
Kendall Jenner
Rumours of Harry’s romance with Kendall, 27, were first sparked in November 2013, but insiders claimed that the pair were “just friends”.
They then headed off on a Caribbean trip where they were seen looking very cosy on a series of yachts.
Things then went quiet, but in January 2016, Khloe Kardashian confirmed the on-off pair were dating – although she wasn’t sure if it was official.
They were then seen having dinner together in LA in April that year.
It didn’t last and Kendall reportedly went on to date actor Orlando Bloom, but it appears the pair just haven’t been able to get away from each other whenever they are both single.
In May 2019, rumours started up again after Harry and Kendall were seen leaving the Met Gala together with some friends.
The couple never confirmed if they were together again or not, but did appear together on James Cordon’s Late Late Show and Kendall went to Harry’s LA concert in November 2022.
Camille Rowe
After a sad split from musician Devendra Banhart, the Victoria’s Secret model, 33, hooked up with Harry in 2017.
The romance was short-lived and they broke up a year later, but that hasn’t stopped Harry from penning a song about her – Cherry.
Things seemed amicable between the pair as she even lent her voice to the track for some French words at the end, while he even mocked her new boyfriend, art collector Theo Niarchos.
In another track from Fine Lines, called Falling, the singer hints that his romance with the model ended because of his cheating.
He sings: “I’m in my bed and you’re not here. And there’s no one to blame but the drink and my wandering hands.”
Olivia Wilde
When Olivia Wilde, 39, split from her fiancé of seven years, Harry was on hand.
The film director shares kids Daisy, 6, and son Otis, 8 with Jason Sudeikis, 47 – who she has accused of putting her into debt during their custody battle.
Olivia met Harry on the set of her film Don’t Worry Darling in September 2020 and sparks quickly flew.
They made their public debut as a couple while attending a wedding together in January 2021.
However, in November last year, it was reported that the pair were taking a break from their romance due to their individual commitments.
“He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A.,” one source told People. “It’s a very amicable decision.”
Florence Pugh
The actress, 27, split with Scrubs actor Zach Braff, 47, last summer after three years together and allegedly found comfort in the arms of Harry.
Florence and Harry are said to have kissed on the set of the film Don’t Worry Darling, before Harry struck up a romance with Olivia.
A source told The Sun: “One night they had a bit of a snog, all very light-hearted and a bit of fun, and that was that.
“It was being gossiped about by a couple of members of production, otherwise no one would have known.
“Harry was very much single at the time and Florence had separated from Zach Braff, although she’d kept the split quiet to — ironically — avoid headlines.”
It’s thought to be the reason the two women fell out but things have since been resolved.