Harry Styles and Kendall Jenner's fans have certainly been confused for a long time whether the two stars were dating or not. In 2014, they had been spotted in Mammoth, California, skiing, and snowboarding and had definitely looked cozy together.
"Kendall snowboarded and Harry skied. They were very cute together," said a source to PEOPLE. "There was a lot of flirting and smiling going on. Harry was a gentleman and even offered to carry Kendall's snowboard to the ski lift."
Then on Dec, 29th, 2015, the two of them were spotted yet again in a restaurant in Anguilla, Eastern Caribbean.
"There has been a lot of flirting, touching and snuggling going on," another source told PEOPLE. "They have acted like a couple. They look very cozy and happy."
The rumored couple continued their vacation the following year, on Jan 2nd, 2016 as they boarded Ellen DeGeneres and Portia de Rossi's yacht in St. Barts. A source told PEOPLE that, "things never got serious between the two when they first met. 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."
In fact, fans speculate that Meet Me In The Hallway may be about the model, as Harry, in an interview with RollingStone said, "She's a huge part of the album' and we all knew that Harry was seeing Jenner around that same time. "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," the 26-year-old singer said.
Apparently, things began to look well for them as a source told PEOPLE in September the same year that the star of Keeping Up With The Kardashians was "so excited and happy about it. She has always cared about Harry."
Indeed it's true because Styles and Jenner were spotted again on a wonderful date in L.A. Moreover, Khloé Kardashian, Kendall's beloved big sister confirmed to Entertainment Tonight that the cute pair were dating. "They were hanging out together," She said. "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 even used air quotes while saying, "But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating. I don't know if they've had that talk yet."
The fans were on it again when Harry had released his song, Sweet Creature. While he discussed the song with Zach Sang, Styles nonchalantly revealed something which made the fans believe that this song was about Jenner. "Sweet Creature is definitely written about one person. In my opinion, I think most of the songs are written for one listener."
In May 2019, Harry and Kendall had bumped into each other at a Met Gala. A source had confirmed to PEOPLE that they weren't a ship anymore as Kendall was in love with her then-boyfriend, Ben Simmons. "Harry was her first real relationship, so there is a lot of history there. But they're just friends."
However, the two of them didn't end the party there. Harry and Kendall along with some other friends had attended an after-party and were spotted leaving together at around 6 am.
Fans wouldn't stop guessing which of Harry's songs were for Kendall. They even theorized that his song, Only Angel was for none other than the 25-year-old celebrity because of the explicit lyrics that pointed all fingers at her. Harry sings, 'I must admit I thought I'd like to make you mine/ As I went about my business through the warning signs' and 'She's an angel/ My only angel.'"
Then again, on Dec 10th, 2019, Styles and Jenner had a reunion on an episode of The Late Late Show with James Corden where they played a rather disgusting game called Spill Your Guts or Fill Your Guts. It was much like Truth or Dare but a grosser version at that. In this segment, the stars had to choose between answering a vile question or eating a disgusting creation that ranged from a salmon smoothie to bull testicles.
It was time for the Adore You singer to answer the question. He had two choices; to answer the question or eat a plate of cod sperm.
"Which songs on your last album were about me?" Jenner asked as the fans cheered loudly behind her.
The fans waited patiently for the much-anticipated answer but instead, Styles was hesitant to answer the simple question. "So, I'd say track uh um..." However, Harry looked at the plate and picked at it.
"Just don't look at it," Kendall suggested.
"Oh yeah, that fixes everything, 'just don't look at it," Harry teased and yelled out to no one in particular, "What are we doing...? what are we doing?"
Sadly, no one found out the answer to that burning question because Harry nibbled on the cod sperm, leading him to ask the greatest one-liner of all-time, "to spit or to swallow, that is the question."
"They are all really good friends and very cool with each other," A source who was close to Harry Styles told to HollywoodLife not long after the Met Gala. "They feel more like brother and sister and will be forever friends who will always be happy to see each other in the future."
Fans also assume that Harry Style's songs, Woman and From the Dining Table are about Kendall as well but I guess we'll never find that out unless Styles confirms it himself.
