Kendall Jenner & Harry Styles are vacationing together in Anguilla for NYE


It’s really difficult to keep up with Kendall Jenner’s love life. She never keeps a guy around for very long – in just the past few months, she’s been rumored to be dealing with Lewis Hamilton, Orlando Bloom, Joe Jonas and Harry Styles. My mean theory: Kendall is boring and she doesn’t have much personality, so guys don’t stick around. My nice theory: Kendall is very focused on her career and setting herself apart from her family, so boyfriends aren’t her priority at this moment. Perhaps both theories hold water. Anyway, back in 2013-14, Kendall was supposedly hooking up with Harry Styles. They went on a few dates and everything sort of fell apart. I never thought it was all that serious between them, but maybe it was just bad timing at that moment. Apparently, Harry and Kendall have reunited and they’re currently vacationing together in Anguilla (you can see the photos here).

Could it be? Will 2016 be the year Kendall Jenner and Harry Styles finally make things official? Well, we can’t speculate on that just yet, but we do know one thing: the two are definitely ringing in the New Year together. A source tells E! News the duo is vacationing on the British Island of Anguilla together in the Eastern Caribbean. They were spotted grabbing a bite to eat at a restaurant called Blanchard’s Tuesday night, and we have the exclusive pictures to prove it.

A few fans at the restaurant were also able to grab a photo, posing with the One Direction singer, while another fan’s tweet about the duo’s dinner date has been gaining a ton of traction.

Kendall and Harry were famously linked from November 2013 through the early months of 2014. The two were photographed getting cozy on several dates ranging from an outing at the Nice Guy in West Hollywood, to a snowboarding trip to Mammoth Mountain and an Eagles concert. However, they continued to deny any dating rumors and never seemed to be able to make things official.

[From E! News]

Is it happening? Do you care? I have some residual affection for Harry Styles for some reason, but I’d rather see him with Gigi Hadid rather than Kendall. But Gigi is too busy dealing with Zayn Malik. And Gigi dated Joe Jonas briefly, while Kendall may have dated Nick Jonas. My point? Gigi and Kendall seem to be picking from the same very limited pool. It wouldn’t hurt either of them to branch out a little bit. Maybe date a lawyer or a med student or something.

Also: is Kendall’s on-and-off thing with Harry the reason why Taylor Swift threw her out of the Girl Squad? Hm…


Photos courtesy of Fame/Flynet.

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59 Responses to “Kendall Jenner & Harry Styles are vacationing together in Anguilla for NYE”

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  1. NewWester says:

    So Kendall might be dating Harry Styles, who used to date Taylor Swift( who I think also was involved with a Jonas brother) Her older sister Kourtney might be hooking up with Justin Beiber who used to see Kendall at one time. Is the dating pool so shallow in the celebrity world that everyone seems to only date everyone’s cast offs?
    Also what is the deal with the sunglasses that seem to cover half the face? I have noticed many of the Kardashian/Jenners wearing them

    • Locke Lamora says:

      If you’re looking for very pretty, very stupid, very shallow, very spoiled, very fame hungry it probably is a small circle. Although this is Hollywood, surely there are tons of people like that there.

    • Ravensdaughter says:

      @NewWester-nicely done. We could easily play Six Degrees of Separation with almost every person in Hollywood, they’re all so incestuous (so to speak).
      She looks so much like Kim now-that’s not a compliment.

      • NewWester says:

        Plus Taylor Swift is dating Calvin Harris who used to date Rita Ora. Rita used to date Robert Kardashian . It always seems to end up back with some member of that family!

    • Lizzie McGuire says:

      i said it before in another posts & I say it again, they all need to date out of that circle. It’s kinda creepy & gross that the K’s are okay with dating the same guys. Harry & Justin have basically dated the same girls over & over.
      PS Harry needs to cut his hair ASAP

    • knower says:

      Taylor Swift, Kendall Jenner, Harry Styles

      All of these people are attracted to the same sex. And for all three, THAT poses a liability…..but also, an opportunity….

      Taylor Swift is basically known as a “Powerbeard” because of her willingess to beard for big male stars in exchange for song fodder. It’s bearding quid-pro-quo. Otherwise known as #winwin

      I can’t believe you guys all fall for this….it shows the PR team coordination totally works.

      • Jennyjenjenjenjenn says:

        I agree! The photos of Harry and Kendall is basically a photo shoot.

      • Halvin Carris says:

        You speak the truth knower. However you MUST speak softly as to not rile up the tween stans. Especially the Swifties. They are the absolute worst!

  2. nicole says:

    His hair is terrible. I don’t get the youth anymore.

    • Locke Lamora says:

      It is. And it’s not the fact that it’s long – it’s the fact that it always looks greasy.
      And most young guys don’t dress like him. Or at least not in my neck of the woods.

      • nicole says:

        Yes, I don’t understand that look. It reminds me of 80s rockers or John Mayer – is that a fair comparison? All greasy and weirdly curled ends. It’s like men’s lifetime lack of hairstyling is a hurdle they can’t overcome if they grow their hair. If you’re gonna have long hair go the Leto route.

      • Locke Lamora says:

        And more and more men look really greasy and unkept lately. I hope that trend goes away soon.

      • bella says:

        I think the kid is sexy as hell – and I say kid because I could be his mom!

        He reminds me of the late INXS lead Michael Hutchense who for me will be the all time essence of sexiness to ever be!
        He was gorgeous…and Harry seems lots like him.

      • marmaduke45 says:

        Totally agree with the Michael Hutchence similarity/vibe. Like Michael, he’s sexy AND charming.

      • bella says:

        Very sexy.
        Michael was the ultimate for me…

      • Tiffany says:

        Not a fan of the hair either but there was a story out there that he was growing it out to donate to Locks for Love or the equivalent.

    • knower says:

      every elder generation says that about the youth.

      see: 1960s hippies versus old people.

  3. Allie says:

    I think they’re just friends. He’s vacationing with his parents and a group of family friends (who Kendall is also close to). Yes I know this. Yes I’m sad about it. I also get the impression that Kendall is into girls. I’ve heard lots of rumors for years now. I think both Harry and Kendall both like the fame game though.

    • swack says:

      I think she’s into girls also – not that it is a bad thing.

    • easi says:

      There were two recent blinds about her liking girls. I think Harry likes guys.

    • Don't kill me I'm French says:


    • caroline says:

      Is she into girls because she’s hanging out with Cara? I noticed that those rumors started after she started hanging around Cara. Because there’s plenty of info of her hooking up with other guys, like Lewis Hamilton.

      • CornyBlue says:

        I have heard these too but never in context of Cara Delevigne.

      • swack says:

        Honestly for me it’s how she behaves around girls and guys. She seems distant from the guys as you never see her holding hands with them or an arm around each other. Whereas there are pictures of her kissing girls on the lips, holding hands, etc. It may be she’s not comfortable with showing PDA in public with guys. Who knows. I just know I did not know Cara was with girls until recently. So it has nothing to do with my opinion on Kendall.

    • Pandy says:

      That’s my theory as well. I think Gigi is also.

  4. Locke Lamora says:

    I think the first is true. On the reality show she comes across as boring, bratty, spoiled and mean.

  5. CornyBlue says:

    These people make so much news and date each other and are Young Hollywood whereas people who are actively working do not do any of this shit.

  6. Sarah says:

    Harry and Kendall are just friends, Harry isn’t dating her. They’re all with the Azoffs too in Anguilla too. That’s the story, actually.

    • caroline says:

      They aren’t even in Anguilla anymore. Last I heard, Harry, his family and the Azoffs were in St. Barts. I also heard Kendall went to Miami for NYE, not sure about this part, but that’s what some people are saying.

      • KB says:

        They’re both in St. Barts right now. I think they just like the publicity of it all. Kendall seems very asexual to me.

      • Janis says:

        I read that PMK is also in St Barts. Would it be too far-fetched that the usual paps/ film crew accompanied PMK/Kendall?

  7. suzysunshine says:

    I’m in Anguilla and yes members of the brat pack are here–Bieber, Harry and Kendall. They can hang pretty low-key if they choose–or they can ARRIVE at the front of the resort surrounded by security (like Bieber did) and then make a scene when gawkers gawk. He must have a horrible advance PR team. Ellen DeGeneres and Dustin Hoffman are here as well–under the radar and unmolested. Anguilla is used to the celebs. If you don’t want to be bothered, don’t make a scene and you won’t be. Bieber sang at Bankie Banx place last night-low key.

    • Snazzy says:

      that just confirms my thinking about Beiber, spoiled brat who loves the attention (and that includes complaining about it!)

  8. antipodean says:

    It’s an old fashioned word, but Harry always looks louche to me. That, and he has a face that just begs to be slapped, something to do with the entitlement factor I feel. Just me?

  9. Renae says: says:

    They are all very young and probably just hang out as friends, some with benefits. Why does media try to make it anything more? Publicists arrange these romances all the time for publicity.

  10. Barrett says:

    Harry styles looks like he will go bald.

    He will be the middle aged guy w the the bald head and back pony tail!

  11. kimbers says:

    Hahahahaha needed a laugh and this did it

  12. rubywoo says:

    Or theory 3, Kendall is clearly gay and the rumours and hook-ups are coming from PMK. It’s obvious and it will come out eventually, she’s a beautiful girl, I hope she finds her happiness.

  13. rudy says:

    Hello…..They are BOTH gay. Both. Definitely.
    So if this relationship is happening, it is only for publicity which is disgusting in my opinion. I really really dislike fake relationships.

    However,maybe they are just friends? Dunno. I like Kendall, or did. I was hoping she would come out.

  14. nena3 says:

    My theory for Kendall’s enigmatic love life is that she likes girls more than she likes boys. It’s just a vibe but it’s very there…

    • knower says:

      @nena3 – I agree.

      And while we’re on the topic, I hate how people make it seem like such a this-or-that, like you can’t REALLY be bisexual.

      I’ve noticed many gay guys can get pretty ‘eye-roll-ish’ when they hear somebody is bisexual. Like, “just pick a side already”…….that’s messed up, sexuality isn’t black or white, and people shouldn’t have to feel to ‘pick a side’ just bc it’s easier for you other to identify who to get with……..seems like a chip on the shoulder for those who respond with that, IMO. Like, “I’m mad it isn’t easier for me to tell who is for me and who isn’t, grr!” Lame.

  15. knower says:

    Blind just went up on Blind Gossip about Kendall and Harry probably kissing at midnight, it being ‘reported’ and then her hospital stay headline bumps out of the news.

    I’m betting this will come true….we’ll find out….

  16. Twinkle says:

    Gross! Harry looks so unbathed and scrawny. If I were young again and that beautiful I would be aiming for someone older and more worldly.

  17. Please no more Kardashian says:

    I think this is a mutually bearding situation. You’ll remember this when it comes out.

  18. Mira says:

    Why does Harry keep doing these PR romances?

  19. racer says:

    Someone wrote it up top- Kendall does seem very asexual. Maybe she’ll become a nun! Kardashian goes to Konvent!

  20. serena says:

    Is dating a Jonas and then a One Direction’s guy a thing? I don’t really get it.. whatever, since she is so young it’s ok to experiment (and yeah I also think she is boring and doesn’t prioritize love right now). As opposite to Kylie, who’s dating Tyga seriously and I think she wants to marry and have kids quite soon too -to blend in with the Kardashian IMO-.

  21. Allie May says:

    I like Kendall. She’s quiet and seems to want to work. Good for her.

    Boring or not, she is being herself and not play acting for ratings for the show. I hope she continues to stay the course.