Olivia Wilde isn’t the only major star Harry Styles has been romantically involved with.
Here is a look at the “Watermelon Sugar” singer’s dating history, from Taylor Swift to Kendall Jenner.
2011: Caroline Flack
Styles was romantically linked to the late Caroline Flack back in 2011 when he was just 17 years old and she was already in her 30s.
Styles met the “X Factor” presenter when he competed on the show along with the other members of One Direction.
“I already knew that he had a crush on me, he’d made it pretty obvious,” she had written in her autobiography, “Storm in a C Cup.” (via Seventeen.) “He’d said it in magazines and he’d said it to friends.”
The pair eventually broke up after being criticized for their age gap.
Flack died in February 2020 at age 40 by hanging herself in her London home.
2012: Emily Atack
Styles dated British actress Emily Atack back in 2012.
The “Inbetweeners” star stayed quiet about her involvement with the singer and didn’t reveal that they dated briefly until two years later.
“We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions,” she told Reveal Magazine (via Hello!) in 2014.
2012-2013: Taylor Swift
Another swift romance for Harry.
Styles dated Taylor Swift for a year. While their romance was short-lived, their relationship lives on forever in the songs each singer allegedly wrote about each other.
Several say Swift’s “…Ready For It” is about Styles, while some believe his “Two Ghosts” is about the “Willow” songstress.
They eventually broke up in 2013.
2013: Nicole Scherzinger
Clearly he likes to date older women.
Styles was romanitically involved with Scherzinger following his romance with Swift.
The Pussycat Dolls singer and Styles “had a dalliance at the end of the X Factor in 2013 and met up again early last year,” a source told The Sun in 2015. “…They hooked up over three years later when Harry had matured and was a member of the world’s biggest band.”
He was 19 at the time while she was 35.
2013-2014: Kendall Jenner
Styles and Kendall Jenner’s relationship took the world by storm when they started dating.
They were reportedly spotted on several dates together.
But while things seemed hot and heavy at first, the pair split shortly after they started seeing each other in February 2014, according to Seventeen. However, that wouldn’t be the last time the two would join together again.
2014: Erin Foster
Styles was rumored to be dating Erin Foster in 2014.
The pair stepped out together for a fun day at a pumpkin patch, according to the Daily Mail.
He apparently met the daughter of David Foster through a mutual friend.
2014-2015: Nadine Leopold
Styles began dating Nadine Leopold in. They were spotted on several outings together including many froyo runs, but they didn’t last long and broke up in March 2015.
2015: Sara Sampaio
Leopold and Jenner weren’t the only Victoria’s Secret models Styles would date.
The singer had a short romance with model Sara Sampaio in 2015 shortly after he broke up with Leopold.
2015: Georgia Fowler
More models for Styles.
After things ended with Sampaio, Styles moved on with model Georgia Fowler.
She even publicized their relationship by posting a video of herself playing Scrabble with Styles to her social media at the time.
2015-2016: Kendall Jenner … again
Styles and Jenner got back together in 2015 after the former One Direction member dated a string of other models.
As Page Six previously reported, they got back together after getting touchy-feely at a New Year’s Eve party.
While things seemed serious for the couple, things didn’t last and they broke up after nearly a year.
2017: Tess Ward
Styles took a break from dating models by linking up with food blogger Tess Ward in 2017.
They secretly dated until she ended things to get back together with an ex.
2017-2018: Camille Rowe
Styles and Camille Rowe dated for a full year before parting ways.
They originally met through a mutual friend.
2019: Kiko Mizuhara
The singer was recently rumored to be dating Kiko Mizuhara.
While she originally denied even knowing styles, their cover was blown when she was spotted with him at his 25th birthday party.
2021-2022: Olivia Wilde
Fans were stunned when the crooner was photographed holding hands with actress Olivia Wilde at a pal’s wedding in January 2021.
The pair continued their PDA-packed romance all over the world, including on gorgeous getaways to Italy and while he took his album “Harry’s House” on tour.
They also worked together on the 2022 film “Don’t Worry Darling,” which Wilde directed and Styles starred in.
The duo’s relationship ended in November 2022 after nearly two years.
2023: Emily Ratajkowski
Four months after his split from Wilde, Styles was seen sloppily making out with model Emily Ratajkowski in Tokyo.
The “Gone Girl” actress could be seen caressing the “Late Night Talking” singer’s face as they French-kissed on a busy street in March 2023.
2023: Taylor Russell
One month after actress Taylor Russell was spotted attending Styles’ Love on Tour, the couple confirmed their romance during a cozy night out in London in August 2023.
Styles and Russell were photographed holding hands the following month, with a source telling Us Weekly that the “Matilda” crooner “definitely sees a future” with the “Bones and All” star.