Harry Styles’ Dating History Proves He’s a True Romantic

Former One Direction heartthrob Harry Styles has had his fair share of romantic relationships since becoming a global icon in 2010. Most recently, the ex-boybander, who is nominated for three Grammy Awards this year, surprised fans when he was spotted getting cozy with girlfriend Olivia Wilde, who directed him in the upcoming film Don’t Worry Darling.

The new couple were photographed holding hands while attending Harry’s manager Jeff Azoff‘s wedding in Montecito, California, in January 2021, while the movie was still shooting in Los Angeles. The shocking snapshots came two months after the Tron: Legacy star and her ex-fiancé, Jason Sudeikis, called off their engagement.

“The pair held hands and looked very much like a loved-up couple,” an insider exclusively told Life & Style of Harry and Olivia at his friend’s wedding. “They seemed very comfortable with each other — almost like they’ve been dating for months, not just weeks.”

Prior to his relationship with Olivia, Harry dated Victoria’s Secret model Camille Rowe. The pair sparked romance rumors in June 2017, when they were spotted at a Fleetwood Mac concert in New York together. The former face of Chloe followed the singer around the globe during his 2017-2018 world tour for his self-titled debut album, but they split in June 2018.

The breakup deeply affected the 1D alum, who went on to write his second album, Fine Line, which was heavily inspired by their relationship. Harry even went as far as to include a recording of the Playboy cover girl’s voice on his song, “Cherry,” one of the sadder songs on the record.

“When we listened back to the album, I asked her to add it in,” he told Rolling Stone in August 2019. “I wanted [“Cherry”] to reflect how I felt then. I was feeling not great. It’s all about being not great. Because you get petty when things don’t go the way you want it. There’s parts that [are] so pathetic.”

Camille isn’t the only woman the U.K. native has written music about. Harry has been linked to Kendall Jenner many times over the years — especially in January 2016, when the former flames were photographed cuddling and kissing on a yacht in St. Barts. In December 2019, the exes appeared on The Late Late Show together when Harry filled in for host James Corden — and the 818 Tequila founder asked Harry which songs on his debut album were written about her.

However, she posed the question during the infamous game Spill Your Guts or Fill Your Guts, so the Dunkirk star opted to eat cod sperm (yes, you read that right) instead of revealing any titles.

Scroll through the gallery below to see Harry’s complete dating history so far.