Styles kept fans guessing about his relationship status when he told Cosmopolitan U. How they act, their body timeline, if they can laugh at themselves. That same month, it was Swift’s turn to plant some clues about their relationship after she was seen out in London wearing a silver airplane chain, which is identical to one owned by Styles. In a 2014 interview with Rolling Stone, Swift admitted she hadn’t dated anyone since Styles. “I feel like watching my dating life has become a bit of a national pastime,” she said.

Kendall Jenner & Harry Styles: When Did They Date? Plus, Everything Else To Know

Although they never officially admitted to dating, it’s widely believed that Will Smith’s son, Jaden was Kylie’s first love back in 2013. Jaden actually introduced Kylie to her lifelong best friend (now, ex best friend) Jordyn Woods when they were 13 years old. They dated off and on until April of 2017, confirming their split just weeks before Kylie is seen holding hands with Travis Scott at Coachella. Following weeks of very persistent rumors, Kylie confirmed that she and Travis are expecting their second child together on September 8. And for any fashion-lovers reading this, ya girl is already out here serving sickening pregnancy style.

It sparked rumours that they were back together, but none bothered to address the rumours. After pictures surfaced of Kenny kissing her best friend’s younger brother, it was clear that these two had a fling. Kendall and Anwar were even snapped with matching love bites. However, before we could even call him her new boyfriend, TMZ reported that they weren’t dating and that “they were just having some fun”. Their chemistry fizzled out before anything awkward came in the way of her friendship with the Hadid sisters.

Forget “Life With Kylie,” it’s all about “Life With Jordyn Woods,” now. Kylie Jenner’s former best friend Jordyn Woods is embracing her inner entrepreneur by launching her own clothing line. The pair, who dated on and off from 2013 to 2019, have now been close for almost a decade.

Before graduating, the brunette beauty was in a relationship with Julian Brooks. He was a football player and she was a cheerleader, making them the perfect match on paper. The two dated for roughly a year before calling it quits in August 2013. Although the couple were rumored by some fans to be romantically interested in each other in 2022, the modeling pair were quick to deny this and insist they were just friends.

Belonging to the uber-famous family of Kardashians and Jenners, her popularity is not surprising. Camille is Harry’s most recent girlfriend that we know of – the Adore You singer has previously been linked to Taylor Swift, Caroline Flack and Kendall Jenner. Those are not the only time that they’ve worked together musically.

November 2, 2016: Styles celebrates Jenner’s 21st birthday.

It seems like when Bad Bunny is in a relationship, he’s committed for a long time, as he and Carliz also dated for five years, per People En Espanol. In 2023, Carliz sued Bad Bunny for $40 million, alleging that he used her recording (“Bad Bunny, baby”) in two songs without her permission. Bad Bunny quipped that he and the jewelry designer “met while sinning,” in a May 2020 Rolling Stone interview. Despite his sultry response, he corrected himself and revealed that he and Gabriela’s first time meeting in 2017 was actually much more low-key. “It was after I sang at a Zion and Lennox concert, here in Puerto Rico. I met her at some restaurant, while I was eating with my parents and my brothers.

Kendall was seen dancing with her sister Kylie and pal Hailey Bieber at Harry’s LA concert earlier this month. They were then photographed enjoying dinner at Nobu in Malibu on August 15, and were joined by Kendall’s sister Kylie Jenner, in photos obtained by TMZ. Their casual dinner comes shortly after Kendall and Devin got flirty via Instagram in August 2020. Kendall Jenner has dated some of the sexiest men in Hollywood and a few of the most skilled players on the basketball court. At last, it appeared the couple were admitting they had been in a relationship together at some point in the past.

“And I’m just not comfortable providing that kind of entertainment anymore.” While she hadn’t sworn off love completely, she told the outlet that she just didn’t have the energy to date, and was perfectly happy living the single life. Obviously, this changed sometime in 2016, when she started dating current boyfriend Joe Alwyn. Kendall has been romantically linked with British singer Harry Styles multiple times between 2013 and 2019.

Prince William warned Prince Harry not to propose to Meghan Markle: memoir

Kendall’s sisters and costars — Kim Kardashian West, Khloe Kardashian, Kourtney Kardashian, and Kylie Jenner — each took turns serving their relationship and friendship-related drama on a platter for the masses. Even her mom, Kris Jenner, opened up about her divorce from Caitlyn Jenner and finding a new love on the series. Given how private Bad Bunny was about his relationship with Gabriela, it’s no surprise that he was also pretty private about his past love, Carliz De La Cruz.

In early April, the two close exes were caught having a joyous side around the streets of Los Angeles together but in separate vehicles. At the time of their breakup it was reported that things ended due to their busy schedules. Fans of the two public figures had been speculating on their relationship ever since an item on the DeuxMoi gossip blog claimed they had been spotted making out at a club in Los Angeles in mid-February. Devin also unfollowed Kendall on Instagram amid the dating rumors between her and the Latin hunk.

Remember when Harry Styles and Kendall Jenner were photographed hooking up on a boat? These two were dating on and off over the course of about three years—and most recently were spotted leaving the Met Gala together in 2019, which, 👀. Jenner and Styles sightings are ongoing, but when it comes to traditional relationship milestones, nothing official has transpired in the public eye. And yet, here we are, still talking about these two and analyzing where things stand today. The singer was recently rumored to be dating Kiko Mizuhara. Styles was romantically linked to the late Caroline Flack back in 2011 when he was just 17 years old and she was already in her 30s.

However, the sighting came just weeks after PEOPLE confirmed Jenner was dating Lakers player Jordan Clarkson and had been for months. In October 2014, the two become Instagram official with a couples Halloween costume. The two publically bumble.com bad gateway dated from here on out, but claimed they were “just friends” until Kylie turned 18 (Tyga bought her a $320k Ferrari for her bday). So now 99% of the internet thinks the two were an item and Kylie has neither confirmed nor denied.