People

Subscribe

Stay Connected

Subscribe

Advertise With Us

Learn More

Skip to content

Celebrity

A Definitive Timeline of Kendall Jenner and Harry Styles' Relationship

Updated

Jeff Kravitz/AMA2015/FilmMagic; Jason Merritt/Getty Images

Kendall Jenner and Harry Styles have a lot of “History.”

From vacationing in the Caribbean together to spending time apart, Jenner and Styles constantly keep the public guessing as to what’s really going on between them. Now, a source tells PEOPLE exclusively that the two are back on after they were spotted on a swanky dinner date in L.A. on Thursday night.

To recap, here’s everything we know about the on-again, off-again romance between Styles, 22, and Jenner, 20.

They grabbed dinner in November 2013
The two shared a low-key dinner at Craig’s restaurant in West Hollywood and were photographed leaving together in Styles’ car. “They’re just friends,” said a source. Jenner also took a moment to tweet that she was single.

via GIPHY

Serious rumors started flying in 2014
The stars were first linked in January 2014 when they were seen going out to dinner and hitting the slopes at Mammoth Mountain in California. (At the time, Styles was 19 and Jenner was 18.) This was the first time they acted overtly couple-y in public.

“Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on,” a source told PEOPLE. “Harry was a gentleman and even offered to carry Kendall’s snowboard to the ski lift.”

Earlier this year, a source told PEOPLE that “things never got serious,” despite their obvious connection.

RELATED VIDEO: See Behind-the-Scenes Moments of Kendall Jenner‘s Glam Life

In December 2015, they vacationed together in Anguilla
Fans spotted them enjoying an intimate dinner together, and they were later photographed getting cozy on a yacht. The two appeared to be all smiles as they boated around the island and were even caught kissing.

Kendall Jenner and Harry Styles in St. Barts
CRYSTAL/PacificCoastNews

A few days later, they hopped onto Ellen DeGeneres‘ yacht in St. Barts, where they were again spotted looking quite couple-y.

Kendall Jenner and Harry Styles in St. Barts
CRYSTAL/PacificCoastNews

Khloé Kardashian tried to explain her sister’s relationship with the One Direction singer, saying that they were, in fact, ‘dating’
A few days after Styles and Jenner’s New Year’s getaway, Kardashian addressed their relationship status in an interview. “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 told Entertainment Tonight. But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.”

Kendall Jenner and Harry Styles in St. Barts
Splash News Online

Same, Khloé. Same.

via GIPHY

They went on a casual shopping trip in April 2016
The pair were seen shopping in Los Angeles. That January, after returning from their vacation, they had partied together at music agent Jeff Azoff’s birthday celebration.

Kendall Jenner and Harry Styles
Holly Heads LLC / Splash News; AKM-GSI

The two currently appear to be rekindling their romance
On Sept. 1, 2016, Styles and Jenner were spotted on a dinner date at L.A. hot spot Tsabel, and an onlooker said that the model “was beaming” all night.

via GIPHY

“They’re rekindling their old romance and Kendall’s so excited and happy about it,” the source tells PEOPLE. “She’s always cared for Harry.”