Team with your favourite skinny jeans and a slick of red lipstick for sophisticated evening vibes. She has also dated Anwar Hadid, the brother of supermodels, Bella and Gigi Hadid who she dated right before Ben Simmons. Harry Styles and Kendall Jenner rumors once again seemed to be true when they were caught having a moment at BRIT Awards, enjoying the after-party in 2020.
And there are even rumors online that Harry and Olivia are actually engaged. The other reason being the nature and timing of how Wilde and Styles reportedly met one another on the set of her film. Some reports from folks who are allegedly close to Wilde and Sudeikis stated that Jason was completely taken off-guard by Wilde’s relationship with Styles, that the two were reportedly still together while she was seeing Harry. Two months later, Bieber told GQ that they “really love” each other and spend lots of time together — but denied that they were in an official, exclusive relationship. Jeffries was spotted with and romantically linked to Bieber multiple times over the course of the following few months.
However, they still didn’t ‘officially’ comment on their relationship. They spent their 2016 dodging the dating questions by the fans and media while constantly being spotted shopping and outings. “Olivia and Harry have an ease to their relationship, they love and support each other, but also let each other be free and work on their own,” a source told Us about the duo’s strong connection. Many famous women have dated Harry Styles, and this list will give you more songs about these lucky girls. In the same interview, Styles admitted that much of his music is inspired by his personal life and relationships.
Here is a look at the “Watermelon Sugar” singer’s dating history, from Taylor Swift to Kendall Jenner. Days later on January 7, Jenner’s elder sister Khloé Kardashian seemingly confirms that the two are an item in some way. In an exclusive with Entertainment Tonight, she tells the outlet that she bets that the two of them are dating, even though she isn’t sure whether Jenner and Styles have actually had “that talk” yet. Jenner happily supports Styles at a concert in Los Angeles, where the supermodel is captured dancing to the singer’s music on the stands beside best friend Hailey Bieber and sister Kylie Jenner. “She worked the room and spent a lot of time with Travis in the beginning, then went to Harry for a while,” said the insider. Jenner remained “hopeful” about her rekindled relationship with Styles but was also “being more careful this time,” added the source.
Television host Caroline Flack was 31 when she started dating the teenaged Styles, and the couple’s 14-year age gap caused a tornado of backlash amongst media and fans alike. “I already knew that he had a crush on me, he’d made it pretty obvious. He’d said it in magazines and he’d said it to friends,” Flack wrote in “Storm In a C Cup” (via People). “I’ve never felt I was much older than Harry anyway. I still feel 18 and probably act that way half the time.” However, the scrutiny on and off line eventually took its toll.
They apparently reconnected in Los Angeles when Bieber had downtime during his tour and were spotted on multiple dinner dates, as reported by TMZ. It was also reported that she was spending a lot of time at his house back in Canada. They first sparked speculation when they were photographed leaving clubs side-by-side and even celebrated Halloween together. It hit a fever pitch when Kardashian attended Bieber’s surprise show in West Hollywood, California — and an anonymous eyewitness source told ET that the two “were nearly inseparable” throughout the night. Jeffries, who was assumed to be Bieber’s girlfriend, battled false reports about previous arrests and “negative attention” from the media.
Speaking Of Basketball Players — Blake Griffin Also Caught The Model’s Eye
“Olivia’s really smitten by Harry,” the insider said after the couple was photographed kissing in Italy. The thing that works for them is that they don’t hide their relationship from the public. “Both of them respect the other’s work and never want to get in the way of each other,” the source said. Wilde and Styles went on to walk the red carpet together at the premieres of Don’t Worry Darling in Venice and New York City in September 2022. Wilde was also seen in the audience at several of Styles’ Love on Tour shows throughout 2022. In late 2012, Directioners and Swifties alike were shocked when rumors swirled of a romance between Harry Styles and Taylor Swift.
February 15, 2021: Wilde praised Styles’ work ethic after production wrapped on “DWD.”
Now, any talk of them dating on the down low has been further dispelled by E!. After Jenner, Styles romanced Australian model Nadine Leopold, and they were seen at The Nice Guy restaurant in Los Angeles. They were seen together in late 2014 and then early 2015, and celebrated Styles’ 21st birthday together.
Styles and Jenner split, however, in April 2016 after People confirmed the model had been dating Los Angeles Lakers player Jordan Clarkson. By September 2016, however, a source told People that Jenner and Styles were giving their relationship another try. “He’s not going to settle down, and she understands that’s just the way he is,” the insider said. ” Jenner asked Styles during a game of “Spill Your Guts.” In the end, Styles chose to eat cod sperm instead of answer the question. Even though this is the first time the two have been publically photographed together, they’ve been romantically linked for quite some time.
Harry and Olivia have been keeping things pretty low key over the past month following Harry’s big Grammy win in March. According to Entertainment Tonight, the couple has been using the past few weeks to “unwind, relax, and really enjoy some one-on-one time.” Olivia is back in the states lamour hookup after spending time in London with Harry while he filmed his latest movie, My Policeman. Well, Harry Styles lets his girlfriend borrow his $87,000 Range Rover. Yup, Olivia was spotted driving Harry’s pricey ride around LA while out with her friends, according to the Daily Mail.
From there, the relationship would go through the ringer — be it “toxic negativity” or rumors she was still with Sudeikis when she and the pop star became romantic (which she has vociferously denied). But as of the date of publication, the couple still seems to be going strong. Harry and X-Factor judge Caroline Flack were linked shortly after the singer competed in the UK talent show. They immediately faced intense media scrutiny for their age gap (Harry was 17 while Flack was 31 at the time), but they still appeared to give things a go.
Harry Styles’ Head-turning Transformation
They first dated for a couple of months from the end of 2013 into the beginning of the following year but the romance didn’t last. As one of the most popular artists in the world, Harry Styles‘ ever-changing dating life seems to always be of public interest. In April 2021, fans of the stars were sent into meltdown after Kendall shared a snap of her dinner on her Instagram Stories, with many freaking out after speculating about whether or not Harry had joined her for the meal. Whether they were together or not, there’s no denying these two are genuinely close friends as fans couldn’t help but comment on how relaxed they looked in each other’s company. Harry and Kendall are said to have begun dating in 2013 until 2014, after they were spotted on a string of outings over a short few months and even went skiing together in January that same year.
