Harry Styles Has No Problem Dating Older Women—A Look Back At His Dating History
...because love is ageless
As young as 17, the public found his love life worthy of attention.
Following the release of photos of Harry Styles, 26, and actress Olivia Wilde, 36, holding hands that went viral over the weekend, a 2012 interview with Daily Mail resurfaced where Harry was asked about his dating life.
“How old is old?” the interviewer pressed. 18-year-old Harry replied, “Any woman older than my mom, Anne—who is 43.”
Most of the women he dated in the past are also older than he was.
Harry, then 17, had a crush on late host Caroline Flack during his days in X Factor UK. “I already knew that he had a crush on me, he’d made it pretty obvious,” she wrote in her autobiography, Storm in a C Cup. “He’d said it in magazines and he’d said it to friends.” They reportedly hit it off but due to criticism on their 14-year age gap, the relationship came to an end.
In 2012, Harry, 18, dated singer/songwriter Taylor Swift—she was in her 20s then. A romance that ended much too soon. Photos were taken. Songs were written.
In 2017, the "Adore You" singer dated model and actress Camille Rowe, four years his senior, and who was allegedly (the fans could vouch for this) the inspiration behind some of the tracks in his sophomore album, Fine Line. Her voice memo was also included at the end of the song "Cherry" (fast track to 3:40!)
The 26-year-old crooner is known for being notoriously private about his dating life, but last weekend, Page Six released photos of Harry and Olivia holding hands at his manager Jeff Azoff’s wedding in Montecito, California.
Such photos sparked dating rumors. There are reports that claim Harry already put a label on the relationship by calling Olivia his "girlfriend" during his speech at the wedding. Fans over on Twitter have mixed emotions: there are reactions that claim the two are just close friends and tabloids are putting a label on it too early. Most defended the two and expressed their support, clipped with Harry’s slogan, #TPWK (Treat People With Kindness).
The two reportedly became closer during the filming of psychological thriller Don’t Worry, Darling (set to premiere 2021-2022), a film currently being directed by Olivia where Harry plays the lead role, Jack, alongside actress Florence Pugh, who plays the role of his wife, Alice.
The lead role was supposed to be played by Shia LaBeouf but due to conflicts in schedules, the part landed to Harry. The changes in the cast made Olivia do a victory dance, "I did a little victory dance when we heard that we officially had Harry in the film, because we knew that he has a real appreciation for fashion and style."
In his historic Vogue cover, Olivia praised the "Watermelon Sugar" singer for his confidence and unconventional approach to fashion: “To me, he’s very modern, I hope that this brand of confidence as a male that Harry has–truly devoid of any traces of toxic masculinity–is indicative of his generation and therefore the future of the world. I think he is in many ways championing that, spearheading that. It’s pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence.”
If reports appear to be true, this is the first public relationship of Olivia since her split with ex-fiancé Jason Sudeikis—they were together for eight years and are parents to Otis and Daisy.
While neither Harry nor Olivia confirmed their relationship, we have to admit, they really look good together.
The Beauties Who Caught Harry Styles' Eyes
The Beauties Who Caught Harry Styles' Eyes
Caroline Flack (2011-2012)
Young Harry and late "X Factor" host Caroline Flack’s romance ended due to criticism because of their age gap of 14 years. Caroline passed away in February 2020. The same month, Harry attended the Brits Awards, a black ribbon pinned to his chest, a symbol of remembrance and mourning.
Photo Credit: @carolineflack
Taylor Swift (2012-2013)
This is one of his high-profile relationships. Everyone’s eyes are on the two young stars. In every public place they went to, photos of them together appeared on social media. It ended too soon. “When I see photos from that day,” he said, in his 2017 "Rolling Stone" cover story, “I think: Relationships are hard, at any age. And adding in that you don’t really understand exactly how it works when you’re 18, trying to navigate all that stuff didn’t make it easier. I mean, you’re a little bit awkward to begin with. You’re on a date with someone you really like. It should be that simple, right? It was a learning experience for sure. But at the heart of it – I just wanted it to be a normal date.”
Photo Credit: @taylorswift
Kendall Jenner (2013-2016)
According to reports, they got together in 2013 and split in 2014. They were seen getting cozy on 2015 New Year’s Eve and was reported to be back together again. In 2016, they parted ways and the two remain friends. Kendall was the special guest when Harry hosted the "Late Late Show with James Corden" in December 2019.
Photo Credit: @kendalljenner
Georgia Fowler (2015)
Back in 2015, the NZ model posted a video on her Snapchat of her and Harry playing Scrabble. Fans were quick to conclude that the two might be dating. Some think the song "Kiwi" was about her. She dismissed the song rumor: "[I] definitely didn’t have a baby. That’s what the song’s all about, so I think it’s highly unlikely.”
Sara Sampaio (2015)
As per "Us Magazine," the two were seen getting cozy and were seen leaving the same hotel in New York City. Both parties didn't confirm the rumors.
Photo Credit: @sarasampaio
Nadine Leopold (2014-2015)
Harry and model Nadine Leopold were spotted several times hanging out in Los Angeles. The singer reportedly helped celebrate Nadine's birthday back in 2015. Neither of them addressed the rumor.
Townes Adair Jones (2016)
The two met once on a blind date and months after, a song was born. “I met her once / and wrote a song about her” he even mentioned her name: “Townes / better swim before you drown”— Listen to “Carolina!” Unfortunately, there was no second date.
Photo Credit: Daily Mail
Camille Rowe (2017-2018)
Harry dated French model Camille Rowe for a year. They parted ways in the summer of 2018. In an interview with "Rolling Stone," music producer Tom Hull, who worked with Harry in his second album, said, “He went through this breakup that had a big impact on him. He had a whole emotional journey about her, this whole relationship. But I kept saying, ‘The best way of dealing with it is to put it in these songs you’re writing.’”
Photo Credit: @fingermonkey
Kiko Mizuhara (2019)
Harry was romantically linked to Japanese-American model Kiko Mizuhara. The dating rumors sparked when the singer was spotted with a group of friends along with Kiko in Tokyo, Japan. During the promo of Fine Line, he mentioned that he spent weeks living anonymously in the city. Kiko denied the rumors.
Olivia Wilde (2020)
At the beginning of 2021, Harry and Olivia were spotted holding hands at the wedding of his manager Jeff Azoff. The two became closer during the filming of "Don't Worry Darling" which Olivia is directing and Harry stars in. Harry reportedly called Olivia his girlfriend during his speech at the wedding.
Photo Credit: @oliviawilde
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