From casual nights out to sharing secrets on late-night TV, here’s a look back at Harry Styles and Kendall Jenner’s relationship through the years.

Nov. 20, 2013: Harry Styles and Kendall Jenner have a date night in West Hollywood

Harry Styles, Kendall Jenner and Model of the Year winner Cara Delevingne. DAVID M. BENETT/GETTY

In 2013, following his split from Taylor Swift earlier in the year, the pair shared dinner at Craig’s restaurant in West Hollywood and were photographed leaving the restaurant in Styles’ car. The meeting sparked rumors of romance that both parties were quick to deny. “They’re just friends,” a source told PEOPLE at the time, while Kendall assured everyone on Twitter that she was, indeed, single.

Flash forward to Dec. 1, 2014, when the pair hung with pal Cara Delevingne (pictured above) at the British Fashion Awards at the London Coliseum, again sparking rumors of a romance.

Jan. 1, 2014: Harry Styles and Kendall Jenner go skiing together

On New Year’s Day in 2014, Styles and Jenner were spotted skiing and snowboarding in Mammoth, California. According to reports, the duo stayed in a house with a group of friends, though they appeared to be coupled up. A source told PEOPLE of the excursion, “Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on.” They also said, “Harry was a gentleman and even offered to carry Kendall’s snowboard to the ski lift.” Talk about a winter wonderland!

Dec. 29, 2015: Harry Styles and Kendall Jenner go on a Caribbean vacation to celebrate the New Year

Harry Styles and Kendall Jenner. SPLASHNEWS.COM

Styles and Jenner ushered in another new year together two years later when they vacationed in Anguilla in the Eastern Caribbean. The pair were spotted by fans at a restaurant on Dec. 29, 2016, and later seen getting cozy on a yacht. A source told PEOPLE, “There has been a lot of flirting, touching and snuggling going on. They have acted like a couple. They look very cozy and happy.”

Harry Styles, Kendall Jenner, Portia de Rossi and Ellen DeGeneres. SPLASHNEWS.COM

Jan. 2, 2016: Harry Styles and Kendall Jenner board Ellen DeGeneres’ yacht

They continued their vacation when they boarded Ellen DeGeneres and Portia de Rossi’s yacht in St. Barts on Jan. 2, 2016. A source told PEOPLE that “things never got serious” between the two when they first met, adding, “He has thought all along that Kendall is hot and was sort of just waiting for a chance to spend more time with her again.”

The source also said of the trip, “New Year’s worked out perfect, and [Harry] loved it.”

Jan. 7, 2016: Khloé Kardashian says Harry Styles and Kendall Jenner are dating

Gotta love when big sisters blow up your spot! Khloé Kardashian said she thought the pair were dating, telling Entertainment Tonight, “They were hanging out together. 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,'” she said, using air quotes. “But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.”

She added that she wasn’t sure if they had defined the relationship admitting, “I don’t know if they’ve had that talk yet.”

Jan. 23, 2016: Harry Styles and Kendall Jenner attend the same party in West Hollywood

Jenner and Styles attended a private party celebrating music agent Jeff Azoff’s birthday at the Troubadour rock club in West Hollywood, California, on Jan. 23, 2016. Jenner’s mom, Kris Jenner, and Styles’ stepdad Robin Twist were also in attendance.

According to E! News, the Jenners arrived at the club about an hour after Styles and spent another hour inside before leaving. Styles reportedly left the venue later in the night.

April 8, 2016: Harry Styles and Kendall Jenner may have been spotted shopping together in L.A.

A fan claimed on Twitter that Jenner and Styles were seen shopping in Los Angeles together with a group of friends. However, the sighting came just weeks after PEOPLE confirmed Jenner was dating Lakers player Jordan Clarkson and had been for months.

Sept. 1, 2016: Harry Styles and Kendall Jenner have dinner in L.A.

Styles and Jenner were spotted on a date in L.A. on Sept. 1, 2016, with an onlooker saying Jenner was “beaming all night.” A source told PEOPLE exclusively the following week that, after getting cozy over the holidays, the pair were “rekindling their old romance,” and Jenner was “so excited and happy about it.” The source added, “She’s always cared about Harry.”

September 2016: Harry Styles and Kendall Jenner are “not officially back together”

Styles and Jenner were rumored to be giving romance another try, but the two were taking things slow according to a source.

The source also said Styles and Jenner were “not officially back together” but were “continuing to talk and see where things go.”

Jenner remained “hopeful” about her rekindled relationship with Styles but was also “being more careful this time,” added the source.

“He’s not going to settle down, and she understands that’s just the way he is,” said the source. “She really likes him, but her heart’s not as invested.”

Nov. 2, 2016: Harry Styles attends Kendall Jenner’s 21st birthday party

Three of Jenner’s rumored love interests showed up for her 21st birthday bash at L.A. hotspot Delilah, and Styles was among those in attendance at the star-studded affair. The guest list also included NBA player Clarkson and rapper Travis Scott (though Scott would begin a relationship with Jenner’s younger sister Kylie Jenner just months later).

A source told PEOPLE Jenner wasn’t with any particular guy and spent equal time with each of them.

“She worked the room and spent a lot of time with Travis in the beginning, then went to Harry for a while,” said the insider.

April 18, 2017: Harry Styles hints that his debut album was inspired by Kendall Jenner

Harry Styles. ISABEL INFANTES/PA IMAGES/GETTY

In 2017, the “Adore You” singer had fans buzzing when he seemed to allude to his relationship with Kendall in a Rolling Stone article. While talking about his debut, eponymous album of the same year, he mentioned the woman that inspired him. “She’s a huge part of the album,” he told the magazine. “Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap … and hope they know it’s just for them.” Could it be that the songs on the album were about Jenner?

May 6, 2019: Harry Styles and Kendall Jenner reunite at the Met Gala

Kendall Jenner and Harry Styles. KEVIN MAZUR/MG19/GETTY; DIMITRIOS KAMBOURIS/GETTY

It’s not uncommon for celebrities to reunite at fashion’s biggest night, but a picture was worth a thousand words when Kendall and Harry were spotted having a conversation inside the event in May 2019. The pair didn’t end the night there. In fact, they didn’t end the night at all — they joined some other pals and kept the party going well into the next morning, and were spotted leaving an afterparty around 6 a.m.

At the time, a source told PEOPLE that they weren’t an item and confirmed that Kendall was still seeing her then-boyfriend, Philadelphia 76ers player Ben Simmons.

The source said of Harry and Kendall, “Harry was her first real relationship, so there is a lot of history there,” adding, “but they’re just friends.”

Dec. 10, 2019: Harry Styles and Kendall Jenner spill their secrets on The Late Late Show

Kendall Jenner and Harry Styles. TERENCE PATRICK/CBS

Fans were sent into a tizzy when the pair hung out on camera as Styles filled in for Corden on The Late Late Show and played the ever-so-enlightening game, “Fill Your Guts or Spill Your Guts.” The easy chemistry between the two had many wondering if they were still an item or simply really great friends post-relationship.

At one point in the game, after reading the question to herself and admitting, “I’m dying to know this,” Jenner asked, “Which songs on your last album were about me?” The audience cheered, but Styles chose to eat cod sperm rather than admit which tracks could be about the TV personality.

Nov. 14, 2022: Kendall Jenner attends Harry Styles’ concert in L.A.

Jenner was seen enjoying a night out at Styles’ concert with her sister Kylie Jenner and Hailey Bieber. The women were spotted smiling and dancing to Styles’ music from the stands in videos shared on social media by concertgoers.

For the outing, the reality star wore a plunging snakeskin halter top while her sister and Bieber sported all-black looks.