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Harry Styles & Kendall Jenner Dating 2014 Wrap Up: A Complete Timeline of Couple's Relationship

First Posted: Jan 31, 2014 10:03 AM EST
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From the time when they met each other to up until now, Harry Styles and Kendall Jenner's dating rumors have been catching many people's attentions, especially the One Direction fans, and making quite news headlines. Check out the complete timeline of the couple's dating relationship below!

Nov. 20, 2013 -- Taylor Swift's former boyfriend spotted with Kardashian clan member: the couple's first official date

One Direction was in the U.S. to promote their most recent album, Midnight Memories. The frontman of the band Harry Styles had reportedly met the American reality star Kendall Jenner at CBS studios in Los Angeles, where 1D was recording a performance for X Factor.

On a rainy night, the pair was seen together enjoying a cozy dinner date at Craig's, a popular restaurant (also, one of Jenner's favorite eateries) located in West Hollywood. When their dinner date was over, the teenagers drove off together through a back exit.

The 19-year-old singer was driving a black Range Rover, while the 18-year-old reality starlet kept closely to her phone, sitting next to him on the passenger seat. Shortly after, Jenner made the date official by following Styles on Instagram.

Harry Styles made an appearance on The Jonathan Ross Show, and when the host asked him about what he was looking for in a girlfriend, he replied: "I think you know when you find someone, I guess. I think, just someone who's nice."

Nov. 21, 2013 -- Morning after the first dinner date: Harry Styles meets the parents, bonds with Bruce Jenner at his beach house in Malibu

"Harry, Niall, and Bruce went golfing," a source claimed. "Is there a better way to win over a girl's dad? It worked -- Bruce loved Harry."

The British boybander won over the protective father's heart by talking about Bruce Jenner's favorite pastime. "Harry wasn't in for an easy ride but things couldn't have gone better, all thanks to golf," the source said. "When Harry and Bruce met at his Malibu home, Harry charmed his way through the visit by talking about golf. Bruce is very protective when it comes to his daughters."

Soon after, Styles spent some quality with Jenner doing a few outdoor activities. "Kendall and Harry hiked the canyon behind Bruce's house," the source added. "Afterwards, they swam at the house. Then, Kendall's half-brother Brody took them surfing."

Nov. 23, 2013 -- 1D Day: Harry Styles keeps his silence about the dating rumor with Kendall Jenner

When one of the One Direction fans asked Styles at "1D Day" event if he was romantically linked to Jenner, he cleverly replied by saying that they do not have anything going on between them. "I mean, we just went out to dinner so... No, I guess," he said. "I don't know. Let's move on, shall we!"

Nov. 24, 2013 -- Harry Styles sleeps over at the Malibu beach house

The One Direction singer was spotted having a breakfast in Malibu after spending a night at the exquisite property of Bruce Jenner.

"Harry went to the beach house late in the evening and didn't emerge again until the morning," a source said. "Harry's obviously had the seal of approval from her dad Bruce, it's the second time in a week he's spent the night at his beach house."

Nov. 24, 2013 -- American Music Awards 2013: Kendall Jenner denies the dating rumors

"No story, we're just friends," said Kendall Jenner. "He's cool." The KUWTK reality star said that she and Harry Styles are just "friends."

Kylie Jenner, who was on her sister's side on the red carpet added: "I haven't met them all, but the few I've met are amazing. They're really, really nice guys."

Nov. 25, 2013 -- Harry Styles and Kendall Jenner go on their second date

The couple's very private rendezvous took place at a super-expensive, members-only SoHo House in West Hollywood. "They leaned in to talk to each other," one of the eyewitnesses at the restaurant, said of the pair's second date. "[Harry Styles] was really animated with Kendall."

At the end of their romantic lunch date and after sharing "two dishes," Styles reportedly picked up the tab for his new love interest. "They definitely plan to hang out more," the source added.

Dec. 7, 2013 -- One Direction's SNL gig: the couple hangs out at a gay bar afterwards

Jenner was spotted Styles' side backstage at Saturday Night Live. After One Direction's gig, the couple went to Therapy, a popular gay bar in New York City, where they spent most of their time in the restaurant area. The duo reportedly stayed for a short while before heading to their next stop of the evening. 

An eyewitness claimed that the two "were having a great time" and "for sure looked like they were a couple. They had a blast."

Dec. 7, 2013 -- Harry Styles and Kendall Jenner leave a hotel together

The pair was spotted together leaving the Gansevoort Hotel in New York City's Meatpacking District. They were instantly swarmed by fans so the security ushered the two through the hotel's restaurant, The Chester.

A source claimed that Styles and Jenner have been in touch ever since the AMAs. "I've never seen Kendall happier and more fan-friendly," the source added. "They came off the elevator holding hands and then she stood and watched while he posed with fans."

Dec. 11, 2013 -- Interview with E!: Kendall Jenner plays coy on dating rumors

The reality star tried her best to keep her silence about the dating rumors. "Nothing to say," she said. "No deets."

Jenner then subtly hinted that she is taken. "We're not single," she admitted as her sister Kylie joined by her side. "We're taken by each other!" she joked while hugging Kylie. "Kendall and Kylie dating!"

Dec. 15, 2013 -- Did Harry Styles spend the night at Kendall Jenner's hotel? The couple makes their own midnight memories in London

Jenner was in London on Dec. 14, as she posted a selfie posing beside the Thames River, which she captioned the photo, "hey Ben!" with Big Ben in the background. While the reality star was enjoying London's skyline, One Direction attended the annual NRJ Music Awards at the Cannes Festival Palace in the southern French city, where the band received two trophies -- Video of the Year for "Best Song Ever" and the International Duo/Group of the Year.

Just few hours later, Styles left his bandmates behind, and quickly flew back to London to see Jenner. He was spotted solo sneaking into the hotel where she was staying at 2:20 a.m. on Dec. 15.

A source close to the Kardashians claimed that Kendall Jenner spent two years plotting to steal the heart of the British singer. "Kendall wanted to make the move on Harry from day one but she was advised by mutual friends he wouldn't be interested until she turned 18," the source said. "The reasoning was that while she was below 18, she'd be too close to the age range of 1D's hardcore fans, who are mainly young teens."

"So Kendall patiently waited until she hit 18 to get in touch with Harry, which she did shortly before the band came to L.A. last month," the source add. "And Harry jumped at the chance to meet up with her."

Dec. 21, 2013 -- News: Brody Jenner says his sister Kendall will break Harry Styles' heart

Brody Jenner said all his sister wants to do is to just have fun, and she is definitely not ready to commit in a serious relationship. "I hate to tell you this, but Kendall will be doing the heartbreaking," he said. "I'm sure she's having a fun time with him. She has a very level head, great head on her shoulders. But they are both so young." He added, "she is at that age where dating is a lot of fun."

Dec. 24, 2013 -- News: Bandmates and friends disapprove of Harry Styles' romantic relationship

It was reported that the dating status of Styles and Jenner might be nothing more than a PR stunt, which hinted that the attention might be tipping more in the reality star's favor to help her career.

"She flew over and surprised him and Harry visited her at a hotel. They're accusing her of using Harry to land London-based modeling gigs," a source said. "Kendall has already told Harry that she wants to move part-time to London to make a go in the fashion world, modeling and designing."

"Kendall's already asked him to appear on her family's reality show, which his family, friends and bandmates are urging him against," the source added.

Harry Styles's friends disapproved of him of dating Kendall Jenner, especially because of her mom, Kris, who has quite a reputation for furthering her daughters' career opportunities. Another source said that the singer's friends "don't want Kris to sink her teeth into him." The source added, "Kris will push them to do joint business ventures. She'll make sure she benefits off them."

Dec. 29, 2013 -- News: Does Harry Styles want to date British girls?

A source claimed that Styles thinks Jenner is "one of the most boring people he has ever met," adding that the thought of socializing with her notorious clan is terrifying for him and he has no plans to make to reality star into his girlfriend. "Harry has a very dry, British humor," the source said. "And thinks he'd be better off with an English girl who gets his sarcasm."

Similarly, the 1D singer reportedly said he also thinks the aspiring model is nothing more than a beauty, who lacks in personality. "Harry finds Kendall very attractive but finds her personality practically nonexistent," the source said.

Styles also expressed his frustration to his friends saying that he is "fed up" with being in the spotlight. "Harry is really down-to-earth guy and he appreciates the opportunities he has in front of him," the source claimed. "But he's really struggling with certain aspects of fame."

Jan. 2, 2014 -- Harry Styles and Kendall Jenner go on a ski trip

The couple allegedly stayed at Mammoth Mountain ski resort in California with a group of friends to spend their holiday vacation together by hitting the slopes.

One of the fans who saw them at the resort took to her Twitter and Instagram accounts (@allieconnolly) to post up a snapshot of herself, posing with the duo. "Casually hanging out with Kendall Jenner and Harry Styles. #dying," she tweeted.

Jan. 2, 2014 -- Kendall Jenner gifts Harry Styles her token of love

The KUWTK reality star reportedly got the "Best Song Ever" singer a gift basket, full of his favorite English food, including English breakfast tea, chocolate, peanut butter and apple juice, so that he would not be homesick while on their publicized ski trip.

"It was a very loving thing to do because she really thought about him and what he likes," a source claimed. "Kendall knows Harry's favorites and how he specifies having English products on tour and was really thoughtful with her present for him."

The basket also came with something more special: Jenner gave Styles a silver and black necklace that a jeweler friend of hers made. The source claimed that Styles was thankful, saying, "he couldn't get over how much care and tenderness went into it."

Jan. 6, 2014 -- News: Harry Styles refuses having his relationship with Kendall Jenner on Keeping Up with the Kardashians

The British boybander reportedly refused to allow the reality television cameras to follow him around on his dates with Jenner, although he himself is a huge fan of the clans' reality series on E! The producers of KUWTK had asked Jenner to let them follow during their previous dates, as well as the ski trip, however Styles strongly insisted that their dates are "personal, not professional."

"Harry has told Kendall that he will not appear on 'Keeping Up with the Kardashians' under any circumstances," a source said. "Harry does not want his love life played out across the world on TV."

Kendall's mom Kris Jenner, the executive producer of the popular reality show, is the one who has allegedly given her daughter the permission to date the 1D singer. "Kris has a double interest," the source added. "Obviously she wants her daughter to have the best relationship with Harry but as the show's EP knows how much of a draw footage of their pair could be. Naturally, the producers want Harry on camera."

Jan. 6, 2014 -- News: Harry Styles is reportedly "hooking up with Kendall Jenner because she's super hot"

Styles allegedly revealed his main reason why he is dating her. "Harry is a playboy," a source said. "Living by his own rules and the rules of a 19-year-old boy who can pretty much dictate the life he wants to live and the life of a guy who can get any girl he wants."

The source also claimed that the rumored couple is "nothing serious" and that Styles "enjoys hooking up with her because she is super hot." The source added, "he can manage her boringness because the other hookup stuff is obviously enjoyable to him, and if he can also do stuff with her that is fun like skiing, he can downgrade her limitations in the boring department. It's a win-win."

Jan. 7, 2014 -- Harry Styles photographed driving Kendall Jenner's Range Rover

The Midnight Memories singer was photographed driving the reality star's Range Rover at Rite Aid in Los Angeles, although Jenner was nowhere in sight with him.

In October, Kendall Jenner posted an image of the inside of her brand new Range Rover via Instagram, which had the distinctive air freshener hanging from the rear view mirror. After fans noticed that the car freshener in her snapshot was the same as that seen in Harry Styles' photo, she consequently deleted the evidence that linked to her fancy car.

Jan. 14, 2014 -- News: Harry Styles reportedly planning a horseback riding date for Kendall Jenner

"He asked Kendall what she'd most like to do when he was back in America and she said horseback riding," a source said. "She told him she adores horses and has been riding for 10 years, and if she wasn't so busy with her fashion career she'd be riding all the time." The source added, "Harry's really keen on Kendall, so he is planning a series of activity dates in 2014."

Styles reportedly told the people around him how he truly feels about Jenner which they think she is nothing but a distraction in his career. "Harry has told his management team as well as his band members that he thinks he's in love with Kendall," another source said. "Obviously they are terrified. His management thinks that she is a huge distraction and are very concerned without the amount of time he's been spending with her." The source added, "they want him to focus on the music right now because he's so big, and have told him not to get too serious with Kendall. Harry is seeing stars and thinks that she is the hottest girl in the universe."

Jan. 15, 2014 -- News: Harry Styles changes his mind, considers appearing on Keeping Up with the Kardashians

Jenner was in talks with Styles, convincing him on appearing on their family reality show, citing Kanye West -- how Kim Kardashian's fiancé initially was also reluctant, but agreed to be featured on the show later on.

"Kris has always seen her children's relationships as business opportunities, so she wanted him on the show," a source claimed. "She insisted Kendall talk to him about it and has made great inroads, explaining what a great opportunity it could be for him."

"Kris pointed out how Kanye was reluctant to do it, which has certainly influenced Harry. He has a lot of respect for Kanye. Harry is now considering making a small appearance, perhaps just in one episode or even a trailer. After all, his band was created for 'The X Factor,'" the source added. "Kris is the one of the best negotiators out there. She always gets what she wants."

Jan. 17, 2014 -- Harry Styles and Kendall Jenner spotted at Eagles concert: the couple's first PDA

The pair was at the Eagles concert at Forum, not only with Kendall's half-sister Khloé, but also with her mom Kris. They were joined by several friends, including Chelsea Handler. Their night out undoubtedly confirmed that they are more than friends and they have been secretly dating since November.

The couple seemed very comfortable with each other as they watched the '70s rock band performing, and they were even spotted cuddling. One of the fans took a photo of Styles having his arms around the Jenner and posted it on twitter. "Harry styles and Kendall Jenner at the Forum last night... @1D_Updates_EU might want to see this...," @ilyharryniall1 tweeted.

Another witness Milennia Vasquez claimed that she met Harry Styles after he accidentally showed her some affection when he mistook her for the reality star. "My dad and I were backstage when suddenly someone hugged me from behind," she said. "I was surprised and I turned around and it was Harry Styles! I was like, 'Oh. My. God. It's Harry Styles!' He looked at me weird and said, 'Oh, I'm sorry, I thought you were someone else!' Right at the moment, I saw Kendall turn around and look at the two of us."

"He really thought I was Kendall. I didn't know what to do. For a couple seconds, I was speechless. I had no words whatsoever. But then I told him I had to take a picture because it was absolutely hilarious" she continued. "He said, 'I'm sorry about that. I'm Harry,' and shook our hands and gave me another hug. He was really nice. I told him I went to see One Direction at the Staples Center in August and he said he remembers that show." She added that he was "definitely flirty" and "Hugging her most of the time."

"They had other friends they were with, but they were staring at each other a lot," she said. "The way he was standing in that picture with his arm around her, that's how he was most of the time... they definitely looked like a couple."

At the SAG Award arrivals, comedian Kathy Griffin, who was standing next to the couple, claimed that Styles "was canoodling with her." As a joke, she stole his coat and posted a selfie on Twitter, wearing it as a proof. "Hey @Harry_Styles! I have ur Saint Laurent coat from last night's Eagles concert. U know where to find me....," she wrote.

Jan. 21, 2014 -- News: Kris Jenner demands Harry Styles quit band for Kendall

Kris Jenner loved all the attention that her daughter was getting and urged Harry Styles to quit his band. The management and the members of the 1D were not happy with Kris' intention and her getting in the way of Styles' music career. "Some of the boys [One Direction members] are concerned that Harry's stealing the spotlight with yet another celeb romance, but they're also furious about Kris meddling in band matters," a source said. "They're worried that she's [Kris Jenner] slowly trying to get him to quit the band."

"Kris is the mastermind behind her daughter's success and financial empire," the source added. "She has endless contacts and a lot of clout, two things that could really help Harry launch his solo career."

Jan. 22, 2014 -- News: Simon Cowell reportedly wants Harry Styles to stay away from Kendall Jenner

Simon Cowell, who signed One Direction to his record label after their impressive performance on his U.K. X Factor, reportedly wanted Harry Styles to stay away from Kendall Jenner and especially her mom-manager.

"Simon knows how controlling and manipulative Kris is because he had dealings with her when Khloé Kardashian co-hosted the U.S. 'X Factor' for one reason," a source claimed. "So when he heard Kris had already asked Harry to appear on the family reality show, he was livid. He told Harry that doing the show would not only be embarrassing, there'd be no benefit to him whatsoever."

The founder of Syco Entertainment was mad when Styles told him about the night Kendall and Kris introduced him to Kanye West.

"By the end of that evening, Kanye was inviting Harry to come into the studio to lay down some tracks. Simon freaked when he heard that!" the source added. "He's really worried about losing control of Harry. He knows his lead singer's been thinking about a solo career, so the last thing he needs is that Kardashians and Kanye digging their claws into the One Direction star and trying to separate him from the rest of the band -- not to mention Simon's record label!"

Jan. 23, 2014 -- News: The couple's relationship confirmed by Amy Willerton

Willerton, who spent time with the pair at the Eagles concert, spilled the beans, confirming that Styles and Jenner are dating and the One Direction singer is happy with the reality star. "I was at the bar getting some popcorn for the show and I hear this voice call my name," she said. "I turn around and it's Harry Styles, and he knew who I am. I realized my life has changed. I thought, 'Oh my God, One Direction watch the jungle."

"We were just chatting. We are a similar age so it's really nice to meet someone doing so well," the Miss Universe Great Britain 2013 added. "He's very happy with his new Kardashian romance, how exciting is that. We've got one of our Brits in the Kardashians show."

Jan. 27, 2014 -- News: Kendall Jenner reportedly planning a nice vacation to celebrate Harry Styles's 20th birthday

"Kendall's dad has a beautiful cliff-top holiday home in Big Sur, California, and she has asked if she and Harry can use the mansion for a private break together," a source said. "She wants them to have some time alone where they can relax and enjoy each other's company. Harry already has everything he wants so she decided to organize something special they can always remember."

In addition to treating him to a romantic break, Jenner is also helping Styles's close friend Nick Grimshaw organize a birthday party in London.

"Kendall is in charge of organizing the party, alongside Radio 1 DJ Nick Grimshaw," the source continued. "She wanted the party to be in London so that Harry's friends and family could all be there."

"The rest of One Direction and a whole host of other celebs will be on the guest list," the source added. "It won't be a tame affair, Kendall will pull out all the stops to make sure it's a night to remember."

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