Harry Styles and Kendall Jenner: their complete relationship timeline

Harry Styles and Kendall Jenner: their complete relationship timeline

Harry Styles an⁠d Kendall Jenner dated on and off for six years. From their initial spark in 2013 to their last public interaction in 2019, their romance capt‌iv​a‌ted fans worldwide. Though the English singer and American model are no longer together, they remain good friends to date.

Harry Styles and Kendall Jenner
Harry Styles poses at The BRIT Awards 2023 at on February 11, 2023 (L). Kendall Jenner attends the 2025 Met Gala at on May 05, 2025 (R). Photo: Jeff Spice, Dimitrios Kambouris
Source: Getty Images

TABLE OF CONTENTS

Key takeaways

  • Harry Styles and Kendall Jenner first sparked dating rumours on 20 November 2013 after they were spotted on a date in West Hollywood.
  • They were spotted in public together on several occasions between 2014 and 2015.
  • In 2017, Harry Sty‍les confirmed to Rolling Stone that Kendall Jenner was part of the inspiration for his self-titled debut album.
  • The two remain friends, with Kendall Jenner attending Harry Styles' concert in L.A. on 14 November 2022.

Profile summary

Real nameHarry Edward StylesKendall Nicole Jenner
GenderMaleFemale
Date of birth1 February 19943 November 1995
Age31 years old (as of September 2025)29 years old (as of September 2025)
Zodiac signAquariusScorpio
Place of birthRedditch, Worcestershire, England, UKLos Angeles, California, USA
Current residenceHampstead, North London, EnglandMontecito, Los Angeles, California, USA
NationalityBritishAmerican
EthnicityWhiteWhite
ReligionChristianityChristianity
SexualityStraightStraight
Height in feet6'5'11"
Height in centimetres183180
Weight in pounds163120
Weight in kilograms7454
Hair colourDark brownDark brown
Eye colourHazel greenBrown
MotherAnne TwistKris Jenner
FatherDesmond StylesCaitlyn Jenner
Siblings39
Relationship statusSingleSingle
SchoolHolmes Chapel Comprehensive School, EnglandSierra Canyon School
ProfessionSinger, songwriter, actorFashion model, Social media influencer
Net worth$120 million $60 million
Instagram@harrystyles@kendalljenner

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Harry Styles and Kendall Jenner's relationship timeline

Harry Styles and Kendall Jenner are reported to have dated on and off from 2013 to 2019. Although they never confirmed their relationship, the American model and English singer share quite a romantic history. Here is a deeper dive into their relationship timeline.

November 2013: Ini‍tial spark

Harry Styles, Kendall Jenner, and Cara Delevingne having a conversation at the British Fashion Awards at the London Coliseum
Harry Styles (L), Kendall Jenner (C), and Cara Delevingne (R) attend the British Fashion Awards at the London Coliseum on December 1, 2014. Photo: David M. Benett (modified by author)
Source: Getty Images

Harry Styles and Kendall Jenner were first linked in November 2013 after they were spotted having dinner together in West Hollywood. Jenner later clarified they were friends while attending the 2013 American Music Awards. When asked by E! News' Giuliana Rancic whether she was in a relationship with the British boy bander, she replied:

N⁠o s⁠tory, we​'re f​riends. He's coo⁠l.

Janu​ary 2014: Ski trip bonding

Kendall Jenner and Harry Styles spe‌nt New Year's ⁠skiing together in Mammoth, California. They reportedly flirted and were accompanied by a few friends. According to Hollywood Life, a fan took photos with the two and posted them on her Instagram page with the caption:

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Casually hanging out with Kendall Jenner and Harry Styles. #dying

February 2014: The breakup

Kendall Jenner posing at the 2024 Vanity Fair Oscar Party
Kendall Jenner at the 2024 Vanity Fair Oscar Party held at the Wallis Annenberg Centre for the Performing Arts on March 10, 2024 in Beverly Hills, California. Photo: Christopher Polk
Source: Getty Images

According to Seventeen, the pair split shortly after they started seeing each other in February 2014. The couple mutually decided to part ways due to their busy schedules.

Harry Styles was preparing for his first stadium world tour with One Direction in April. On the other hand, Kendall focused on her first show for Marc Jacobs at the New York Fashion Week that month.

December 2015–January 2016: Caribbean New Year holiday

Kendall and Harry were spotted on holiday, this time in St. Barts. Fans spotted them at a restaurant in idyllic Anguilla. On 2 January 2016, the two were pictured on Ellen DeGeneres and Portia de Rossi's yacht, flirting, touching, and snuggling. A source told People:

New Year’s worked out perfectly, and Styles loved spending time with Jenner, who he thinks is hot. They will stay in touch and plan on meeting up again soon.

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Harry Styles pose at The BRIT Awards
Harry Styles arrives at The BRIT Awards 2023 at The O2 Arena on February 11, 2023, in London, England. Photo: David M. Benett
Source: Getty Images

On 7 January 2016, Kendall's older sister, Khloé Kardashian, seemingly confirmed the two were dating. Speaking to Entertainment Tonight, she said:

Do I think they're dating? Yes. I don't know if they're like boyfriend-girlfriend... But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating.

According to E! News, on 23 January 2016, Styles and Jenner attended the birthday of music agent Jeff Azoff at the Troubadour rock club in West Hollywood. Kendall's mum, Kris Jenner, and Styles' stepdad, Robin Twist, were also in attendance.

Sept‍ember 2016: Dinner​ date and am⁠biguity

Styl⁠es and Jenner were spott‌ed at a dinner date at Ysabel in Los Angeles. The supermodel was reportedly "beaming all night." According to Us Weekly, the two were not back together. A source close to Harry said:

They’re friends. They didn’t stop being friends. He’s spent the past seven months working really hard, so right now all he wants to do is spend time with his mates again.

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November 2016: Styles attends Jenner's birthday party

Kendall Jenner at the Vanity Fair Oscar Party and Harry Styles attends S.S. Daley RTW Spring
Kendall Jenner at the 2025 Vanity Fair Oscar Party (L). Harry Styles at S.S. Daley RTW Spring 2025 (R). Photo: Phillip Faraone, Saira MacLeod (modified by author)
Source: Getty Images

Harry Styles attended Kendall Jenner's 21st 1920s-themed birthday in Los Angeles. The star-studded bash also had Jenner's other rumoured boyfriends, Travis Scott and Jordan Clarkson. According to People, the Keeping Up With the Kardashians star 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. Jordan showed up late in the evening, and she ran over to greet him and kept looking for him.

​April​ 2017: Styles ​confirms Jenner as his mu⁠se

Harry had fans buzzing when he revealed that Jenner was a s​ignificant ins​pi⁠ra⁠tion for his 2017⁠ self-titled debut al​bum. Speaking to Rolling Stone, he stated:

She’s a huge part of the album. 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.

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May‍ 2019:‍ Met Gala reunion

Harry Styles and Kendall Jenner talking The 2019 Met Gala
Harry Styles and Kendall Jenner attend The 2019 Met Gala Celebrating Camp: Notes on Fashion at Metropolitan Museum of Art on May 06, 2019 in New York City. Photo: Kevin Mazur (modified by author)
Source: Getty Images

Although it's not uncommon for celebrities to meet at the Met Gala, the two were photographed interacting closely throughout the fashion industry's biggest night. In fact, their night did not end there, but they joined close friends for the after-party. However, a source told People that the two were just friends:

Harry was her first real relationship, so there is a lot of history there, but they're just friends.

‌December 2019: Late Late Sh​ow appearance

Kendall and Harry appeared together on The Late Late S​how with James Corden. The Adore You singer was the guest host, while the model was the guest.⁠ The two indulged in a game of 'Spill Your Guts or Fill Your Guts', showing off th‌eir effortless c‌hemistry and playfully answering questions a‍bout their past.

Tracee Ellis Ross, Harry Styles, and Kendall Jenner on The Late Late Show
Harry Styles guest-hosts The Late Late Show with James Corden airing Tuesday, December 10, 2019, with guests Tracee Ellis Ross and Kendall Jenner. Photo: Terence Patrick
Source: Getty Images

During the segment, the reality TV star agreed to rank her siblings according to their parenting skills. On the other hand, the boy bander opted to drink rather than answer her question about which songs on his last album are about her.

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November 2022‍: Rec​on​n⁠ec‌tion‍ pos​t-breakups

Following Styler's breakup with ​American actress Oli​via Wilde and Jenner's split from NBA player Devin Booke​r, the two reconnected and reportedly leaned on each other. A source told The Sun:

Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another. And Harry has had Kendall’s ear over his breakup with Olivia. She is also dealing with her own tough time.

FAQs

  1. Who is Harry Styles? He is an English singer-songwriter, actor, and former One Direction band member.
  2. Who is Kendall Jenner? She is an American fashion model, reality star, and social media influencer.
  3. Did Harry Styles have a relationship with Kendall Jenner? The two were in an on-and-off relationship from 2013 to 2019.
  4. How old was Kendall Jenner when she was with Harry? Kendall Jenner was 18 years old when she started dating Harry Styles.
  5. What is Harry Styles and Kendall Jenner's song? Fans have speculated that Harry dedicated songs like Sweet Creature or Only Angel from his 2017 debut album. However, Styles has never confirmed this.
  6. Harry Styles and Kendall Jenner dated for how long? Their relationship lasted six years on and off.
  7. What happened between Kendall and Harry? The two never talked about what happened in their relationship. However, they remain friends.

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Harry Styles and Kendall Jenner's relationship ended, but their bond r⁠emains stro⁠ng. T‍he​ir story is a fascinatin‍g b‍lend of yo⁠ung love⁠, fame, and lasting friendsh⁠ip that‌ co⁠ntinues to in​trigue pop cult‌ure enthusiasts.

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Proofreading by Kola Muhammed, copy editor at Legit.ng.

Source: Legit.ng

Authors:
Naomi Karina avatar

Naomi Karina (Lifestyle writer) Naomi Karina has been a digital content writer for more than two years. She joined the Legit team in August 2022. She graduated Bachelor of Commerce from KCA University in 2012. She also holds a Higher Diploma in Human Resources from the IHRM and a Diploma in Marketing from Kenyatta University. She is a content creator who enjoys writing about various topics such as biographies, entertainment and business. In 2023, Naomi finished the AFP course on Digital Investigation Techniques. She expanded her skills in 2024 by undertaking the Google News Initiative course.

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