Harry Styles‘ romantic life is seemingly always in the headlines, and now, the singer may once again be off the market.

The former One Direction member-turned-solo star was just spotted kissing another star, but it’s not the only person he’s been linked to recently.

We’re taking a look back at all of his romances, past and present.

Caroline Flack

He began dating the English television presenter while competing on The X Factor in 2011, and they broke up in 2012. The pair were criticized for their relationship, due to their 14 year age gap.

Emily Atack

Harry had a short-lived romance with the English actress in 2012. Although there wasn’t too much that came from it, Emily’s 2010 tweet about Harry is still a bit funny to think about after all these years.

“Let’s pretend he’s 18 at least! Then there’d be only One Direction he’d be going – to the bedroom!”

Taylor Swift

The singers garnered a lot of media attention once word got out about their relationship. They dated from the end of 2012 to early 2013, and there has been no “bad blood” between them since their breakup.

Since their breakup, Taylor has allegedly referenced their romance in her songs “Style” and “Out of the Woods,” with Harry rumored to do the same in One Direction’s “Perfect.”

Nicole Scherzinger

Outlets reported that the two briefly hooked up in 2013. They met while he was still on The X Factor, where she served as a judge at the time.

Kendall Jenner

Another one of Harry’s high-profile relationships, the two of them had a fling back in 2014. Sister Khloe Kardashian ended up confirming the two were dating again in 2016, but didn’t know what their “title” was. Harry and Kendall split again shortly afterwards, and have since remained on good terms.

Erin Foster

Harry was rumored to be in a relationship the writer back in 2014, and again in 2015. A source cleared everything up shortly after the 2015 rumors began, and confirmed Harry and Erin hooked up in the past, but are now “just friends.”

Nadine Leopold

The two of them reportedly started dating at the end of 2014, but it fizzled out in March 2015 due to busy schedules. However, this breakup is more unique than others, considering a source claimed that before this relationship, Harry had never been dumped by a girl.

Sara Sampaio

Another day, another short romance in 2015: rumors of Harry and Sara’s romance began as reports came out that Sara spent the night at Harry’s hotel room in New York. Whatever the pair were, they did not last long together.

Georgia Fowler

Following a viral video, outlets confirmed fan speculation involving Harry and Georgia and spending time together away from the cameras in fall of 2015. Alas, that romance also ended fast, but the video of the two playing Scrabble seems to live on.

Tess Ward

The musician and food blogger reportedly met through mutual friends, and were “really into each other” in 2017. The pair split two months after news of their alleged relationship broke out.

Camille Rowe

Like his previous relationship, Harry and Camille met through a mutual friend, Alexa Chung, in 2017 and began seeing each other shortly afterward. They ended their relationship in summer 2018 after a little over a year, and with that, the inspiration behind his album Fine Line was born.

Kiko Mizuhara

It’s unclear how close Harry was with Kiko back in 2019 amid romance rumors, but it was a bit mysterious that Kiko claimed to have never met him one day, and next thing you know, find her at his 25th birthday party.

Olivia Wilde

After meeting on the set of Don’t Worry Darling, the two of them started dating in January 2021, and became a highly publicized couple. Their breakup in November 2022 was also highly publicized, and although amicable, was difficult for Olivia at the time.

Emily Ratajkowski

Harry and Emily’s makeout session in Tokyo sent social media into a frenzy in March of 2023. There’s no confirmation about the nature of their “friendly” relationship is, or was.

Taylor Russell

The Bones and All actress made headlines after being spotted backstage at Harry‘s concert in Vienna back in July 2023.

A month later, she was seen getting close to Harry after the premiere of her play in London, and later seen hopping into a car alongside the superstar. There’s still no official confirmation about the status of their relationship amid the romance rumors.