In an interview with Piers Morgan, Styles said he “didn’t know if things would turn romantic” with Jenner but she denied romance rumors again at the American Music Awards soon after. Both Kendall Jenner and Harry Styles have notoriously kept their dating lives private, despite their immense fame. Though these two stars are clearly dear friends, fans have long speculated about just how close they really are. The One Direction star’s love life has been highly speculated about following his split from long-term girlfriend Olivia Wilde, but Harry is currently single. While their romance was short-lived, their relationship lives on forever in the songs each singer allegedly wrote about each other. Jenner was seen enjoying a night out at Styles’ concert with her sister Kylie Jenner and Hailey Bieber.

The song “Falling” becomes an attempt at self-reconciliation after hurting another person, and names places they went together in Los Angeles. The way Rowe offered a French hello — “coucou” — on the voicemail appears on two other songs as well. As private as Styles is about his dating life, he’s said that many of his songs are inspired by past relationships.

October 27, 2014: Taylor Swift releases 1989, which fans speculate was inspired by her newly single life

The pair, who were thought to be dating in 2019, had been to a party together. Newly-emerged footage has shown Harry Styles went “home” with a model just hours after pashing supermodel Emily Ratajkowski. Harry Styles is certainly living it up in Tokyo – newly-emerged video shows him going “home” with a model just hours after pashing Emily Ratajkowski. Rumors of Emily Ratajkowski and Pete Davidson dating emerged after  Gossip Instagram account DeuxMoi posted an anonymous tip on her Instagram stories that the two were on a date in Brooklyn, New York. “CANT BELIEVE IM SAYING THIS ANON PLS. EMRATA AND PETE DAVIDSON ON A DATE IN BROOKLYN TOGETHER. HOLDING HANDS AND ALLLL,” the message said.

Although for most people it is nothing more than a pipe dream, for one woman who lives in Los Angeles, it became a reality a few years ago when she went on a blind date with one of the members of One Direction. It was stated that Townes Adair Jones and Harry seemed to hit it off immediately after being put up on a blind date with each other by Townes Adair Jones’s sister, the actress Gilland, and some of Gilland’s friends. It is not the first time that Harry has shown interest in dating a lady who is significantly older than he is. In 2011, the then-17-year-old had a relationship with Caroline Flack, who was then 31.

Harry Styles and Nadine Leopold dated in 2014-2015.

Emily and Brad were said to have hung out at an exclusive Oscars party in 2020 and they’ve moved on slowly from there. “Brad was crushing on Emily at the 2020 Vanity Fair Oscar party,” the insider told OK! “She was happily married [to Sebastian], and Brad respected that.” Now that she’s single, though, the source said Brad took the opportunity to make his interest in Emily known. She’s always thought Brad was cute, and the way she saw it, what did she have to lose? Ultimately, the model reportedly dumped Styles because of this inability to commit. “Nadine wanted a more serious commitment from Harry,” a source close to Leopold told Hollywoodlife.com.

From October 2012 to January 2013, Styles found himself in a whirlwind romance with the pop star, with dates spanning from a day out at the Central Park Zoo in New York City to a romantic getaway to the British Virgin Islands. “I don’t know if they’re like boyfriend-girlfriend. Nowadays I don’t know. People are weird with stuff. So, I don’t know their title.” Styles’ relationship with the French model seemed to be his longest to date. The world may never know what exactly went down between Styles and Rowe (or if they were even actually dating), but it still makes me feel warm and fuzzy inside to know these two might have found a way to stay friends.

American Music Awards 2019: All The Fabulous & Flirty Fashion!

‘I will say, ‘I thought that’s what you liked about me, that I had this big life? But when they are actually in the relationship, they start to get resentful. In an exclusive video obtained by MailOnline, a passer-by caught them in a clinch as they took cover from the rain next to a silver people carrier. Emily was filmed passionately kissing Harry last week after a gig on the latest leg of his aptly named Love On Tour concerts.

Jan. 1, 2014: Harry Styles and Kendall Jenner go skiing together

She even publicized their relationship by posting a video of herself playing Scrabble with Styles to her social media at the time. “They were hanging out together. Do I think they’re dating? Yes. I don’t know if they’re, like, boyfriend-girlfriend,” Kardashian says. “Nowadays, I don’t know, people are weird with stuff. So I don’t know their ‘title,'” she adds with air quotes.

A source for US Weekly revealed in 2019 that Harry Styles and Kendall Jenner have remained close friends after their breakup. “Harry and Kendall are great friends and always have been.” the source said, adding that they are both very busy but when they do get to hang out “they always have a blast. It’s an easy, super chill friendship.” In Jan. 2021, Wilde and Styles were spotted holding hands at his agent’s wedding, and they’ve been pretty solid ever since. Though they’ve kept quiet on their romance, the duo has dropped a few hints about their romance. In Dec. 2021, Wilde did tell Vogue that she was “happier than ever” in life. And in May 2022, Styles referenced “trusting” Wilde as a director while shooting Don’t Worry Darling…

Harry Styles has not been known to publicly date any older woman. During his time in One Direction, the singer was linked to many young female celebrities such as Taylor Swift and Kendall Jenner. However, he has not been linked to any older women romantically. This did not include sex, which led Styles to have conflicting feelings about intimacy and love. First linked in 2020, Kendall is currently dating NBA star Devin Booker. While she still chooses to stay tight-lipped about her relationship, the supermodel has been a bit more forthcoming about Devin, confirming that the the pair were dating during the KUWTK reunion.

Sources reported that Harry and Olivia had fallen for each other while on set and had officially acknowledged their relationship in early 2021. The couple featured in various magazine covers, such as Harper’s Bazaar, where they professed their love for each other openly. Harry Styles has been in many relationships throughout his career, but the longest one to date has been with American model Camille Rowe, whom he first met back in July of 2017.

Bieber reportedly reached out to Baldwin while he was resuming his romance with Gomez at the end of 2017. In May, Baldwin told The Times that they were in a “mature” place and had moved past the “weirdness.” By the end of June, the couple became Instagram official and were essentially inseparable. “Justin’s been friends with her for a while,” a source XCheaters mobile login told ET. “They know each other through mutual friends. The thing with Justin and Selena is that when they’re together, they’re together, when they’re apart, they’re apart. As in, they’re no longer attached at the hip.” A source told ET in March that Gomez also felt overwhelmed with the media attention whenever she and Bieber were seen as an item.

The two had dating rumors surfaced when the two were walking around New York City and were sitting courtside at a New York Knicks game at Madison Square Garden on the day before Valentine’s Day. On the day devoted to love, the comedian posted an NSFW picture of him nude on a couch with a reflection of EmRata taking the picture. The mother of two and Styles, who met on the set of their film Don’t Worry Darling back in September 2020, first stepped out as a couple as they were photographed holding hands while attending a wedding together in January 2021.

One day later, the rapper Lil Twist posted a photo of himself, Bieber, and Palvin on Twitter — but quickly deleted it. Gomez later re-posted the photo to her own Twitter account, adding a vague comment (“……”), according to Hollywood Life, but then deleted hers as well. The public first sensed tension in May 2012, when, according to the Mirror, Gomez posted a photo of herself firing a gun at a shooting range with the caption “releasing some stress today.” She then deleted her Instagram account. Now that the pop star is officially off the market, let’s take a look at all the women who have managed to capture his coveted attention — and perhaps why his engagement has been seen as a complete wild card. It’s hard to remember a time before Justin Bieber posters were featured on bedroom walls across the world. He rocketed to fame at just 13 years old, sauntered through an impossibly seamless puberty (in a physical sense, at least), and continues to capture the hearts of Beliebers everywhere.