Harry Styles' Dating History: Taylor Swift & Kendall Jenner To Olivia Wilde

Styles' first high-profile relationship was with British TV and radio presenter Caroline Flack. The pair, who shared a 14-year age gap, met in 2011 after Styles and his One Direction bandmates competed on X Factor. Flack would later go on to host the show, as well as Love Island and BBC's Dancing With The Stars.

While they only dated briefly, the pair kept their romance private until paparazzi photos of Styles leaving Flack's home one morning let the world in on their secret. Because of their age difference -- he was 17 at the time, while she was 31 -- the relationship was branded controversial.

Looking back on the romance in her autobiography, Storm in a C Cup, Flack recollected: “I already knew that he had a crush on me, he’d made it pretty obvious. He’d said it in magazines and he’d said it to friends.”

She continued: "We were both single, we got on well and we had a laugh. It was only when it became public knowledge that things turned sour."

Flack added: “After that anyone could say anything. In the street, people started shouting at me ‘pedophile’ and ‘pervert.’”

According to Seventeen, the TV host began getting death threats from One Directioners, ultimately causing Flack and Styles to split.

Styles tweeted at the time that their breakup “was a mutual decision,” calling Flack “one of the kindest, sweetest people I know,” per US Weekly.

Flack died by suicide in February 2020 at age 40 after struggling with mental health. According to several publications, Styles paid a tribute to his ex at the Brit Awards that month by wearing a black ribbon on his lapel -- a traditional symbol of remembrance or mourning. See it below.

In the spring of 2012, Styles was dating model Emma Ostilly, who appeared in the band's "Gotta Be You" music video. Both 18 at the time, the young pair made headlines after they were spotted kissing on a date night in Auckland, New Zealand. Although they had tried to keep their involvement quiet, the pictures lead to yet another storm of abuse from One Direction fans, culminating in Ostilly shutting down her Twitter account.

Styles and British actress Emily Atack were briefly involved in 2012, although nobody knew about it until a couple of years later. The Inbetweeners and Celebrity Juice star, who is five years older than Styles, opened up about the relationship to Reveal Magazine in 2014, per Hello!.

"We were never boyfriend and girlfriend," she said. "We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions."

According to Tell Tales, the actress had her eye on Styles way before the two got together, tweeting a couple of years prior: “Does Harry from One Direction have to be 16?”

After a fling with Made in Chelsea reality star Caggie Dunlop, 32, the English crooner embarked on his fourth romantic relationship of 2012 with Taylor Swift. The famous musical duo dated between October 2012 and January 2013, with Swift reportedly breaking things off with Styles over an argument they had during a trip to the Caribbean.

According to a US Weekly source, the former One Direction member "said something he shouldn't have," although Hollywood Life put the breakup down to Styles kissing another woman behind Taylor's back.

Reminiscing about the relationship years later, the "Steal My Girl" singer told Rolling Stone in 2017 that "certain things don't work out."

"There’s a lot of things that can be right, and it's still wrong," he said, via Entertainment Tonight.

The former couple is believed to have put their whirlwind romance into song, with fans speculating that Taylor's "Out of the Woods" and "Style" songs, as well as "I Knew You Were Trouble" and "I Wish You Would," were about Styles. Meanwhile, his "Perfect" and "Two Ghosts" songs are thought to be about Swift.

Speaking to Rolling Stone, Styles shared: "I mean, I don't know if [Swift's song] are about me or not… but the issue is, she's so good, they're bloody everywhere."

He continued: "In writing songs about stuff like that, I like tipping a hat to the time together. You're celebrating the fact it was powerful and made you feel something, rather than, 'This didn't work out, and that's bad.' And if you run into that person, maybe it's awkward, maybe you have to get drunk, but you shared something. Meeting someone new, sharing those experiences, it's the best s**t ever. So thank you."

Proving he definitely has a thing for older women, Styles bagged Pussycat Dolls lead singer Nicole Scherzinger back in 2013 when he was 19 and she was 35.

The former exes reportedly first met in 2010 when he was on X Factor with his band and she was one of the judges. According to a 2015 report from the U.K. Sun, “they hooked up over three years later when Harry had matured and was a member of the world’s biggest band,” per an insider.

The source said the pair “had a dalliance at the end of the X Factor in 2013 and met up again early last year.”

Scherzinger paid a sweet Instagram tribute to Styles in 2017 when he released his debut solo album.

"He’s all grown up! So proud and happy for him!" she wrote, sharing a selfie of the two that you can see below.

After allegedly having another fling with an older woman, this time in the person of Rod Stewart's daughter, Kimberly Stewart, who is 15 years his senior, Styles moved on with socialite and reality star Kendall Jenner, 26. The couple took the world by storm with their relationship in November 2013, after paparazzi photos showed them grabbing dinner in L.A. While it only lasted until February 2014, the duo rekindled their romance a year later. Scroll down for more details.

After his three-month relationship with Jenner, Styles was rumored to be courting David Foster's daughter, Erin Foster, in October 2014. Spotted together at a pumpkin patch, per the Daily Mail, the British singer and the American writer and performer, who is 12 years older, never got serious though, only dating casually for a short time.

Styles went on to date a few Victoria's Secret models, starting with Nadine Leopold, 27. First spotted together in November 2014, they were a couple for about four months, going their separate ways in March 2015.

According to Tell Tales, it was Leopold who broke things off with Styles because she reportedly wanted a more serious commitment from the singer.

After Jenner and Leopold, Styles went on to date another Victoria's Secret model in 2015. The "Adore You" singer had a brief romantic liaison with the Portuguese supermodel Sara Sampaio, 30, with the pair spotted kissing in June that year.

Styles' foray into the world of Victoria's Secret supermodels continued with Georgia Fowler, 29, in October 2015. The pair sparked dating rumors after the New Zealand model shared a Snapchat video of the two playing Scrabble, which you can watch below.

While their romance was short-lived, fans speculated that Fowler was the muse behind Styles' "Kiwi" 2017 hit song.

Styles and Jenner sparked reconciliation rumors in December 2015 after getting cozy on a yacht on New Year's Eve in St. Barts. According to media reports at the time, there had been "something going on with those two for a while," with the KUWTK star being the one "who made the first move" by inviting her ex on the trip.

Jenner's older sis Khloé Kardashian confirmed they were back together in January 2016, telling _ Entertainment Weekly_: "Do I think they're dating? Yes. I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff. So, I don't know their title."

Styles and Jenner reportedly dated until April that year, grabbing dinner together in September 2016. While it's unclear when they called it quits, the two are still reportedly great friends, reuniting at the 2019 Met Gala and again months later on The Late Late Show With James Corden.

Jenner is now famously dating NBA star Devin Booker.

After being linked to fashion stylist Pandora Lennard during his on-again, off-again relationship with Jenner, Styles took a break from dating models. In the spring of 2017, the singer was romancing chef and food blogger Tess Ward, 31, although the pair kept things very private. According to Page Six, they secretly dated until June that year when Ward put an end to it to get back with an ex-boyfriend.

Styles dated French model Camille Rowe, 31, for a little over a year in what seemed his most serious relationship yet. The pair were first linked in July 2017 after attending a Fleetwood Mac concert in NYC and stayed together until July 2018. According to Seventeen, the singer even introduced his girlfriend to his family, suggesting they were the real deal while it lasted. Styles was reportedly broken up about their split, per a 2019 Rolling Stone [interview-(https://www.etonline.com/harry-styles-opens-up-about-sex-drug-use-and-reuniting-with-one-direction-131216).

Styles has now found love with Booksmart director Olivia Wilde. After meeting on the set of the erotic thriller Don't Worry Darling, the pair are now almost one year strong, going public with their relationship in January. Despite facing criticism for their age difference, it seems Styles and Wilde couldn't be happier, with their families giving their stamp of approval.