Harry Styles and Kendall Jenner were first linked together in 2013. Throughout the years, they kept denying their romance even after their PDA filled date on a yacht. With random reunions here and there, it begs the questions, what was up with the two?

We’re here to tell you.

After years of readers begging for us to write about this popular duo, we come bearing information that may either confirm your suspicions or shock your fantasies.

Let’s do a quick background information run through because I like to get all the public facts out there and have you wonderful readers, draw your own conclusions as we navigate the information. Then, we expose the tea!

RELATIONSHIP TIMELINE

On November 20, 2013, Kendall and Harry were spotted grabbing dinner together.

At the time, Kendall was 18 and was known for starring on the popular reality TV show, Keeping Up With The Kardashians. Harry was 19 and it was still part of the popular boy band, One Direction.

Their reps denied that they were dating at the time and claimed that “They aren't 'dating.' They are just friends. That was like the first real time they hung out. We will see what happens.”

By the way, when a “source” talks to mainstream media, it’s the celebrity’s people reaching out. You know, their publicists, managers, and sometimes the “source” is actually the celebrity themselves. This is just some general information keep in your minds.

A few days after their date, Harry was asked about it and he responded rather awkwardly about whether or not they were dating.

He said, “I mean, went out for dinner, but no, I guess.”

The 2013 American Music Awards were coming up a few days later on November 24th and it was reported that Kendall was presenting the award for Favorite Pop/Rock Album which is a category that One Direction was nominated in. Turns out, Kendall didn’t even present that award, but it was Kelly Osbourne and Nicole Richie who were presenting it.

Weird.

She later told People Magazine that, “We’re friends. He’s cool, yeah, he’s cool. You go out with one person, you’re automatically dating them.”

Nothing really happens between them for the rest of November.

Then, One Direction performed on Saturday Night Live on December 7, 2013.

A source told E! that Kendall spent time with Harry backstage, but they didn’t attend the after-party. However, there were no photos of them backstage.

They did leave the hotel together in New York City that day.

On January 3, 2014, Kendall and Harry took a skiing trip together with a group of friends in Mammoth, California.

A source told People, “They were very cute together. 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.”

My favorite part of that quote is the “there was a lot of flirting going on.” It’s like who’s the source that’s that close to them on the skiing trip to be able to tell? LMAO anyways.

In February 2014, they are reported to have spent Harry’s 20th birthday together as Kendall threw him a big bash at her family’s clifftop mansion, but there are no photos from that alleged birthday party. Weird.

By the end of that month, February 23rd to be exact, their teams reported that they have split up after three months of dating due to “work commitments.”

Uh huh…

You guys are keeping track though, right? That was two public outings from November 2013 until January 2014, unless you count the spottings without photos.

Then in December 2014 at the British Fashion Awards, they ran into each other when Kendall was with that other irrelevant model, but nothing more went on.

And here’s Kendall looking at Harry all lovey dovey.

We don’t hear from the two of them ever again until December 2015.

On December 30, 2015, they are photographed vacationing on the British Island of Anguilla together in the Eastern Caribbean. E! News published exclusive photos of them eating at the restaurant Blanchard’s.

Fans tweeted about the spotting and some even posed with Harry.

Then, their most iconic candids come out—their PDA filled candids on Ellen DeGeneres’ yacht in St. Barts.

Here they are pictured on December 31, 2015, as they rang in the new year together.

Photo credit: AKM-GSI

Everyone was FREAKING OUT because as you can see from their on/off timeline, this the only PDA filled candids that they presented at the time.

Here they are on January 1, 2016 as Harry playfully grabbed Kendall’s ankle.

Here they are on January 2, 2016, joined on the yacht with Ellen and her wife, Portia de Rossi.

Here’s some more pictures of them playfully messing around… with Harry taking an interest in Kendall’s feet lmao

Photo credit: Splash News

Those candids are kinda cute.

Then on January 7, 2016, Kendall’s older sister, Khloe Kardashian, held an exclusive interview on Entertainment Tonight to talk about Kendall and Harry’s St. Barts PDA filled pictures.

She says that she’s pretty sure that Kendall and Harry are dating.

“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. But I mean, they were in St. Barts together hanging out, so to me that’s dating.”

Here’s a thought Khloe…. why don’t you just ask your sister?

Anyways, that week at the People’s Choice Awards, Ellen who was vacationing with them said, “They’re very sweet. I like both of them individually and I like them together as well.”

So everyone was like “TOGETHER????”

Yet Harry and Kendall are still not confirming anything.

On January 25, 2016, they both attended the same private party for music agent Jeff Azoff. However, they arrived and left separately.

Kendall’s mom, Kris Jenner, and Harry’s stepdad Robin Twist, were also at the party.

Then on April 6, 2016, this fan taken photo of the duo had all popular news outlet swirling with questions: IS THAT HARRY AND KENDALL?

This is the photo that had them all confused.

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Every news article that reported on the photo seemed unsure. Here’s People and JustJared’s confusion on the picture.

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To me, I found this whole scenario weird. Just reach out to their reps for a comment? I don’t get it. It’s obviously Kendall in the photo and probably Harry as well considering the posture, clothing, and HAIR.

However, there seems to be a whole theme circulating this couple and that theme is UNCERTAINTY.

I guess the reason why they were so hesitant to confirm or deny their spotting was because People claimed that Kendall was actually secretly dating lakers player Jordan Clarkson for months.

Either way, Harry and Kendall were rumored to be together in September 2016 when they were spotted on a dinner date in LA yet… there were no photos of them. However, sources (her rep) claim that she was “beaming” during their reunion and that the two of them are rekindling their old romance.

In an interview with Rolling Stone in April 2017, Harry was talking about his debut solo studio album and how that there is a mystery woman who is “a huge part of the album.” He also said, “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.”

I really wish I knew what the hell that meant…..

I should also probably note that during this time, Harry was seen with a bunch of different women and he was rumored to be dating Camille Rowe for some time.

Then we don’t hear anything from the two ever again until May 2019 where they were spotted talking together at the Met Gala.

The media such as Mirror Online claimed that they were “two of the last people to leave” and that they were “relaxed and happy in each other’s company.” The Daily Mail reported that they left the after party minutes apart.

You know, Kris Jenner hard at work, the usual.

They were spotted leaving the Met Gala after party together though.

And that was that for the Met Gala which brings us to the last occurrence to include in this inconsistent timeline—December 2019.

in December 2019, they were both on The Late, Late Show where they played Spill Your Guts.

It was a very cute segment between the duo as Harry opted to eat cod sperm instead of admitting what songs he wrote about Kendall.

They were kind of flirting and everyone was like, “are they… back together?” Everyone claimed they had so much chemistry and were adorable together.

Nothing else got confirmed.

Fast forward to February 2020 and Kendall and Harry are spotted at the Brits after party. Harry was dressed in yellow and Kendall was in sparkly green. Hard to miss them with those colors.

Then in April 2020, Harry was seen driving alongside Kendall and her rumored boyfriend, Fai, on a motorcycle while the duo rode in a purple convertible.

Such an….. odd thing.

And the fact that this was happening during quarantine? HUH? That’s it for their timeline now. Time to expose.

What really went on between Harry and Kendall?

The funny part is… nothing went on. They were a contracted public relationship (PR) this whole time! Yes, this. whole. time.

Now this may not come as a surprise to you guys because we’ve said it multiple times and if you’re a fan of either one of them, you’ve probably called it.

Of course I’m not going to leave it at that. Let’s get into the details.

When they first had their arrangement, my source tells me that Kris Jenner wanted Kendall to get with a high status pop star in order to benefit her modeling career.

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I already knew this for many years, but I wanted to double check with my source to make sure I’m remembering their history correctly.

If you’re an avid reader of this blog, you’d know that Kris tried to get Kendall to flirt with Justin Bieber and see if things hit it off between them. We told the story of how Justin got mad at Kendall for doing that and blah blah. You can read more down below.

An inside story on Justin Bieber and Kendall Jenner

So it makes sense that the pop star of choice was next fellow big thing—One Direction. Although, I should note that this Justin and Kendall information took place in 2010.

For Harry’s team, they wanted the sexuality rumors to come to a halt and all in all they wanted to make him the “womanizer” and the “stud.” That has been his ongoing image his entire career even when he was still part of One Direction. He was always seen with all kinds of beautiful women, but he’s never tied down. Harry was also seen with a lot of older women… I’m taking 30 and up while he was a teenager.

I’m pretty sure you’ve all heard Shallon Lester tell the story of Harry kissing her on her youtube channel. Stan twitter has been running with that video in my twitter mentions all day because they don’t believe her, but wasn’t that Harry’s persona? A bunch of older women? Anyways, someone please remind me to ask her more about that because… that’s wild if it’s true.

So in 2013 when Kendall and Harry were first seen together, it was approximately a year after Harry’s initial PR setup with Taylor Swift. That was a nightmare PR for both of them, their teams, and everyone involved. However, this ain’t about Taylor.

Learning from that mess, both Harry team and Kendall’s team (aka Kris Jenner the genius), wanted to play the PR in a friendly and mysterious way.

One of the main rules in a PR setup is to DENY DENY DENY in order to build speculation. The more you wonder, the more you’ll talk about them, right? Where’s the fun in the drama unless you don’t know all the details? So in every typical PR, both their teams will deny the relationship and claim that they are very good friends during the first couple of outings.

After that date, Kendall started following Harry on Instagram.

Here on ESMG, I love giving you guys the timeline because we encourage thinking for yourself. We love laying out the facts on a platter and telling you to think before we expose.

So going back to their first date in November 2013, they grabbed dinner together and everyone was speculating about the relationship. Both their reps claimed that they were just friends to ensure more mystery between the fanbases. Harry was still part of One Direction and they wanted to start up some momentum for the band while Kendall was really trying to launch her modeling career and stray away from the Kardashian/Jenner association.

Four days later it was the 2013 American Music Awards. Kendall’s rep released news that she’s going to presenting the award that One Direction is nominated in. Guess what? That never happened as the timeline shows you. They just leaked those news to create momentum. This works in favor of three parties: Kendall, Harry, and the AMAs themselves.

Have you guys ever seen when award shows tweet or post the seating arrangement of where celebrities are going to be placed? Most times it’s controversial. “Oh my god, Selena Gomez and Justin Bieber are going to be sitting next to each other even though they’re broken up?” It’s all BS. They do that to hype up the show in order to create momentum and the seating arrangement ends up getting “changed” the day of the show.

You can see above that the seating arrangement at the 2019 AMAs showed that Selena Gomez and Taylor Swift were sitting next to each other. That never happened. Taylor refused to associate with Selena that night and you can read why down below.

Exposing The Truth About Selena Gomez and Taylor Swift's Friendship: What Happened Between Them at the 2019 AMA's?

Back to Hendall.

Kendall and Harry ended up not interacting at the show however, their fake date went pretty well. Their PR arrangement was set in a way that they’ll renew the contract depending on how it goes. Of curse they’re not going to contract them for six months if the PR fails.

The contract was then renewed until February 2014, but there were only TWO REAL SPOTTINGS. Well a PR isn’t just about pictures, but it’s about what “sources” report to the media. Those sources are their respective teams.

Kris Jenner hard at work.

Harry and Kendall’s PR is very interesting though and it takes a different route than most. Anyways, they ended up “breaking up” in February due to “work commitments.”

This whole time, neither Kendall or Harry confirmed anything. Their teams barely confirm anything too but everything is SPECULATED. That’s the point: create momentum and mystery. Every time a certain event/date takes place, it makes everyone wonder, “are they going to show up together?” If the relationship was confirmed, you’d just assume they’re coming together and where’s the fun in that?

Then Harry and Kendall ran into each other at the same event in December 2014. Due to the lack of confirmation, no one knows what this “run-in” means so everyone is once again speculating.

The next time we see the duo, their pictures are like no other. However, there are two key details that I didn’t write in their relationship timeline:

Kendall Jenner was hospitalized for “exhaustion” in late 2015
Zayn Malik had left One Direction and the band was releasing their last album together in November 2015

God, the timing is so perfect. PRs are just crafted so beautiful, it brings a tear to my eye.

BOOM, SET THEM UP IN A PDA-FILLED YACHT VACATION FOR NEWS YEARS.

What do I always say? It’s not a PR without our favorite beach/yacht pictures.

Suddenly, Harry seems interesting to the public eye again. Everyone stops questioning their sexualities and no one is questioning what form of “exhaustion” Kendall was in the hospital for.

Pop quiz! Exhaustion is a keyword for what in Hollywood? I need rehab.

Anyways, their star studded PR dates last less than a week. They’re spotted from December 30, 2015 until like January 2nd, 2016. Khloe Kardashian is then making claims, but not confirming their relationship.

Their contract basically states that they will be seen here and then, but not often together.

You know, it’s very chill.

So I keep preaching about keeping the mystery alive, right? That’s why when that fan taken photo of the duo came to light, the media was like “omg they’re so cute… IF that’s them.” It’s like who else would that be? Why don’t you reach out for their reps for comment? Why aren’t their reps providing an answer? It all goes back to speculation and mystery. You see, mainstream media and celebrity teams go hand in hand.

Harry and Kendall seem to have the relationship chemistry of a cardboard box and yet everyone talks about them, why? It’s the mystery that accompanies their never-confirmed relationship.

What makes Harry and Kendall work is that they’re very good FRIENDS! They enjoy each other’s company so when they have to hang out for publicity reasons, it’s not a drag. Imagine being forced to hang out with someone you don’t enjoy hanging out with?

That’s the main reason why they seem to have an ounce of “chemistry.” They’re just friends. They got along very well on “Spill Your Guts” because they’re GOOD FRIENDS. They’re not like those PRs that have nothing to talk about.

Kendall Jenner As A Person

Surprise! As-a-person (AAP) posts are VERY popular here on ESMG, but we don’t often write them because in order for us to comply an AAP post, we have to know so SO much information about the celebrity to the point where it allows us to do a personality analysis. This isn’t the case for Kendall and Harry, but I’ll treat you guys to a quick paragraph on what I do know about the two.

Kendall is not a mean person, but she is your typical Hollywood rich model. The rich hang with the rich and those with a status that can benefit them. Coming from the Kardashian/Jenner clan, Kendall knows what she has to do and what she has to say to remain in the good graces of the public.

She’s built to act a certain way and be a certain way. We have elaborated a bit on her relationship with Kylie Jenner in their younger years and how Kylie was jealous of her, but they do maintain a nice relationship. However, there is some tea to be spilled in the upcoming part 2 post of Kylie Jenner and Travis Scott.

Kylie Jenner's Shady Past and Jealousy of Kendall

There isn’t much to say about Kendall considering she has a personality of a cardboard. She’s pretty ignorant and kind of stupid. I mean do you remember her Pepsi ad? Or the fact that the most she’s done during this current Black Lives Matter movement was to post the “tag 10 people and post BLM” chain crap. Kendall is down with the flow. Whatever her publicist tells her to do, she’ll do it.

She had a big part to play in the relationship of Justin and Hailey Bieber. They were a trio for the most part. Kendall actually had a spine when it came to the Selena x Biebers drama so that was interesting to see.

Kevin Mazur/MG19/Getty Images for The Met Museum/Vogue

If you guys have any other questions about Kendall and how she is AAP, you can comment down below and I’ll try my best to answer them. Y’all know me, I’ll draw blanks until you ask the question.

Harry As A Person

Again, if I knew a lot of information, he’d get his own AAP post, but I don’t have that so here we are. But if you as stans can spread this post, maybe a possible Harry and Kendall insider can know of this blog and reach out! Win for the both of us ;) anyways…

Harry Styles is also like Kendall in the sense that she’s ignorant, but down with the flow. Celebrities like them will only participate in something once it’s popular. Fans will now harass their faves if they didn’t speak up about the BLM movement and that’s exactly what happened with Harry. After a couple days of harassment, he posted about it. Where was that energy beforehand? It wasn’t there because ignorance was in its place.

Homeboy is gorgeous though I’ll give him that.

For example, Harry is a Zionist because he doesn’t know any better. However, at your grown age you should know better. After Demi Lovato got harassed for going to Israel on what was a brainwashing trip, she went and educated herself on the issue between Palestine and Israel. Harry hasn’t had that energy because he is ignorant. He takes what people around him support and he soaks it up hence the BLM movement and his random support.

I’m not saying he doesn’t support it, he does. It’s just that he does so because it’s popular to do so. It’s not necessarily a bad thing, but I’ve never heard of Harry taking the time to genuinely educate himself (I mean most celebs are stupid so that’s not shocking).

Another thing, you guys have asked about if he is really as woke as he seems in interviews.

Fun fact, interviews are SCRIPTED most of the time. Especially when you hear those “hard questions” that really test a person’s woke-ness. Most times, the celebrity in question is given the interview questions beforehand and they sit long and hard with their publicist as they brainstorm the perfect response. Their perfect response then comes off as them “thinking hard” as they answer when in reality they’re all acting.

So what I just explained is something that I’ve heard happening several times with Harry.

Also, he’s not the stud that his team makes him out to be. He often keeps his real life hidden, but he’s genuinely a nice dude (minus the Zionism).

Were the songs really written about Kendall?

Uh, no!

Musicians don’t owe the general public anything, but a cute story. If the story fits, use it!

Harry ate cod sperm instead of admitting which songs were about Kendall because the answer is NONE.

Rare picture of Kendall and Harry idk when

It’s like when The Weeknd sang, “I almost gave a piece of me to you” in the midst of Selena Gomez’s kidney transplant story. Yeah…. I’m sure elite celebrities are going around begging for organs in the blood-sucking industry they work in.

In Hollywood, organs are as easy to obtain as gum is for us locals.

Anyways we are getting off topic.

All I’m saying is just because the celebrity says it (or hints it), doesn’t mean it’s true. They are public figures and it is their job to entertain considering they are in the world of entertainment. Nobody cares about the truth, they just want a good story.

If I didn’t care about the truth, I would have bullsh-tted some crap here and then, but then again I’d risk being sued or just losing credibility.

damn these rare pics really be trying to convince me they were real

Speaking of which, I hope you guys know that whenever the media leak news about a celebrity, that celebrity is almost always in agreement with them. It’ll be like “okay you leak that and I’ll just deny it.” So it makes me laugh whenever stans have a meltdown over something the media has reported they’re spamming their fave like “sue them!!!!” Honey… they got the first draft of the article like 6 weeks ago.

Another thing to note is the fact that I’ve heard from numerous people that while Kendall and Harry were “dating” in public, the two of them were actually dating other people low key. One of my sources told me that there were times that you can actually see lowkey candids of Harry or Kendall with other people who they were rumored to be dating within inside Hollywood circles. If any readers wanna drop some info in the comment section below and entertain us all, do it!

Before I end this post I want to emphasize something.

why are there so many rares of them ????? lol

When it comes to PR contracts, there’s different forms depending on WHY there is a PR and WHO is in a PR. In the case of Kendall and Harry, they were your typical model-musicican PR. Other popular forms of PR are musican-musician or actor-musican. It’s very rare to have a model-model PR because models are often irrelevant in terms of pop figures. Musicians tend to have an emotional connection with the public due to their stories that they tell through their music so you’ll often pair up a musician with a model.

This was seen with Gigi Hadid and Zayn Malik in their earlier years before their relationship took a Jelena-turn and became real.

So that wraps up the Kendall Jenner and Harry Styles post! Since these two were not really drama filled and instead had the personality of a crouton, I thought I’d emphasize a bit more on the technical agreements of their beautifully crafted PR arrangement.

Let me know your thoughts down in the comment section below. You can comment anonymously so take advantage of that. I will be replying back! Hope you enjoyed.

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The Truth About Harry Styles and Kendall Jenner's Relationship History and Who They Are As Individual People