TheI Feel Prettyactress previously dated theSaturday Night Livealum, 29, for two months beforeUs Weeklyconfirmed in December 2022 that they had called it quits. Ratajkowski’s connection with Davidson marked her first foray into the dating scene after she separated from estranged husband Sebastian Bear-McClard, with whom she shares 2-year-old son Sylvester, that July. Harry and Taylor were first spotted together when they cozied up on a Central Park date in 2012. Throughout their time together, the two singers were photographed packing on the PDA all over New York City, wearing matching necklaces and jetting off on a romantic getaway together. Following their split, the pair reportedly wrote tons of songs about each other. The “Ever Since New York” artist and the actress surprised fans when they went public with their relationship just two months after Olivia officially broke off her engagement.

The pair were spotted by fans at a restaurant on Dec. 29, 2016, and later seen getting cozy on a yacht. A source told PEOPLE, “There has been a lot of flirting, touching and snuggling going on. They have acted like a couple. They look very cozy and happy.” Neither the “Kiwi” crooner nor theGone Girlactress have further addressed their relationship status.

For anyone who raises an eyebrow at Taylor being older than Harry, that’s nothing compared to who he dated in the months after their breakup. His rebound relationship was with former Pussycat Dolls lead singer, Nicole Scherzinger, who was 35 at the time, compared to Harry who was not yet 20 years old. As she has with most of her past relationships, Taylor wrote a song or two about her time with Harry. While she seems to have written multiple songs about Styles, there’s one in particular that really stands out.

“ said on multiple occasions that he was intimidated by Taylor, which is why he would not attend any events where she was being honored, or any award shows unless he was nominated,” the insider said. After the New Zealand model shared a Snapchat video of her and Styles playing Scrabble together in October 2015, they had fans convinced that they were dating. Some people even speculated that the musician’s 2017 hit “Kiwi” was about Fowler, which she laughed off. That’s what the song’s all about, so I think it’s highly unlikely,” she said on Australia’s The Morning Show. Taylor Swift is one of the most celebrated music icons of the generation with a massive fan following. The ‘You Belong With Me singer’s life, both professional and personal, have made headlines.

Around the same time, Olivia split from her fiancee, Jason Sudeikis, with whom she shares two children. Here, a look back at Harry Styles’ dating history—from his boy band days to being Wilde-ly in love (see what we did there?). Harry Styles is one of those people the world will never stop obsessing over . From a teenage heartthrob during his One Direction days to a feminist icon and 21st Century rockstar. The 26-year old is a force to be reckoned with, and he’s showing no signs of slowing down.

The rumored relationship was pretty much confirmed when the stars were spotted smooching on a yacht in Italy that summer, but both continued to play coy. And do you want to get into all of his rumored romances and flings? Emily had in recent months been linked to serial dater Pete Davidson.

2013: Taylor Swift

“Certain things don’t work out,” Styles later said of their relationship, in a 2017 interview withRolling Stone. “There’s a lot of things that can be right, and it’s still wrong.” A source close to Jenner told ET at the time that there had been “something going on with those two for a while” and it was Jenner “who made the first move,” inviting Styles on the trip. In an October 2017 interview with Nick Grimshaw on The Radio 1 Breakfast Show, Styles admitted that he used to research dates.

Considering the pair dated during December 2012, it’s safe to say her B-day is within Harry’s knowledge. While Taylor was in her 20s during her time with Harry, it may shock some fans to know that Harry was only 18 years old! However, the couple allegedly met for the first time after Harry’s birthday, so he technically never knew the singer while he was underage. It’s not often that Taylor Swift’s exes write their own songs about their relationships with her, but that’s exactly what Harry Styles did. Released on his debut solo album, following Taylor’s songs, “Two Ghosts” is said to be about Taylor.

Zayn Malik and Selena Gomez had a dinner together holding hands and kissing each other. Are they dating?

Kendall and Harry have been hooking up on and off for literally ever, including that legendary time they were photographed making out on a boat. These two have serious chemistry, and if you don’t believe me, I have evidence. “He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A.,” one source told People. The film director shares kids Daisy, 6, and son Otis, 8 with Jason Sudeikis, 47 – who she has accused of putting her into debt during their custody battle. In another track from Fine Lines, called Falling, the singer hints that his romance with the model ended because of his cheating. After a sad split from musician Devendra Banhart, the Victoria’s Secret model, 33, hooked up with Harry in 2017.

As for Styles, fans have wondered if certain solo songs were inspired by this relationship, as well aswhether or not 1D’s track “Perfect” is about Swift. With lyrics like “And if you’re looking for someone to write your breakup songs about / Baby, I’m perfect,” it’s hard to deny the connection. At the time, Taylor was roughly 19 years old when she started dating the “Gravity” singer.

2016: Kendall Jenner … again

Despite the ups and downs of her personal life, Wilde is “ready” to find love. “[She’s] making it clear she’s available, and she isn’t looking for anything less than an amazing guy,” a source told Us earlier this month. Harry has been linked to Kendall Jennermany times over the years — especially in January 2016, when the former flames were photographed cuddling and kissing on a yacht in St. Barts. In December 2019, the exes appeared on The Late Late Show together when Harry filled in for host James Corden — and the 818 Tequila founder asked Harry which songs on his debut album were written about her. The following year, dating rumors sparked between Harry Styles and Japanese-American model Kiko Mizuhara after they followed each other on Instagram. As reported by theDaily Mail, the two apparently met when Styles was jet-setting back and forth to Tokyo over the course of a few months.

A Timeline of Everything Harry Styles Has Said About Taylor Swift

Earlier this month, Ratajkowski was caught packing on the PDA with Styles on the streets of Tokyo, where he performed two Love On Tour concerts on Friday, March 24, and Saturday, March 25. The couple, known as “Hiddleswift” caught everyone by surprise — including Swift. Just one month later, pictures surfaced of the two kissing at the beach in Rhode Island, solidifying their relationship.

From their first meeting at the Kid’s Choice Awards to their friendly reunion at the 2023 Grammys, here’s everything to know about their whirlwind romance and where things stand between the stars now, nearly a decade later. Alyssa Bailey is the senior news and strategy editor at, where she oversees coverage of celebrities and royals . When she’s not working, she loves running around Central Park, making people take #ootd pics of her, and exploring New York City. Ratajkowski was previously spotted at one of Styles’ Paris concerts in July 2022. The We Are Your Friends star was spotted watching the show next to Styles’ then-girlfriend Olivia Wilde. Apart from this, Zayn Malik’s ex-girlfriend, Gigi Hadid also does not have a problem with Selena and Zayn being a couple.

The former One Direction member raised eyebrows earlier this month when he was caught kissing Ratajkowski on the streets of Japan after performing in Tokyo. According to footage published by the Daily Mail on Saturday, March 25, the twosome locked lips while leaning against a parked vehicle. Olivia Wilde has mixed feelings after ex-boyfriend Harry Styles was spotted packing on the PDA with Emily Ratajkowski.

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