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Harry Styles’ Romantic History: From Taylor Swift To Kendall Jenner, Holding Hands With Olivia Wilde & More

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Harry Styles, Caroline Flack


Harry Styles has had a number of relationships since he stepped into the international spotlight in 2010 and we’re taking a look back at them right here.

Harry Styles, 26, has been making girls swoon with his handsome looks, irresistible charm, and musical talent, ever since he stepped onto The X Factor stage for a televised audition to Stevie Wonder‘s “Isn’t She Lovely” in 2010, so it’s no wonder he’s led a steady romantic life over the years. Although the contestant-turned-superstar has many admirers from all over the world, only a few ladies have been lucky enough to be a part of his love life since he broke onto the music scene with his band One Direction and later started a successful solo career. From the late English television presenter, Caroline Flack, to his most recent rumored flame, actress and director, Olivia Wilde, we’re taking a look at all the gals who’ve been romantically linked to the British hunk.

Caroline Flack

Harry Styles and Caroline Flack arrive at the Shoreditch House for a private party in 2014, three years after their rumored romance. (Backgrid)

Harry and Caroline met when she was a presenter on The X Factor. Rumors started going around about Harry having a crush on the British beauty around 2011, and shortly after, they both made waves when reports claimed they were dating. Harry was 17 and Caroline was 31 at the time.

Although neither confirmed nor denied a romance (Harry consistently said in interviews that they “just get on really well”), Caroline opened up about their connection years later in her autobiography, Storm in a C Cup, which was released in 2015. “I already knew that he had a crush on me, he’d made it pretty obvious,” she wrote in the book. “He’d said it in magazines and he’d said it to friends.”

“It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season,” she continued. “After that anyone could say anything. In the street people started shouting at me ‘pedophile’ and ‘pervert.’”

The two eventually split and moved on in their love lives, but sadly Caroline died by suicide at the age of 40 in Feb. 2020. Harry was spotted wearing a black ribbon as a “symbol of remembrance or mourning” to honor her at the 2020 BRIT Awards just a few days after her passing.

Emma Ostilly

Emma Ostilly
Emma Ostilly, seen here at the 3rd annual amfAR Inspiration Gala New York at The New York Public Library in 2012, reportedly dated Harry in 2011. (MEGA)

Harry was spotted kissing American model Emma Ostilly in New Zealand not too long after his split from Caroline. She later appeared in the One Direction music video for “Gotta Be You”, which premiered in Nov. 2011.

Emily Atack

Emily Atack
Emily Atack, seen here leaving The Palace Theatre in London, reportedly dated Harry in 2012.

Harry was rumored to be dating actress Emily Atack back in 2012 but she didn’t confirm it until 2014. “We were never boyfriend and girlfriend…We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions,” she told Reveal Magazine.

Caggie Dunlop

Caggie Dunlop
Caggie Dunlop, seen here attending Fran Cutlers Halloween party at The Berners Tavern in 2019, reportedly dated Harry in 2012. (MEGA)

In 2012, Harry also reportedly dated actress Caggie Dunlop, who starred in the reality show, Made in Chelsea, for a brief time.

Taylor Swift

Harry Styles, Taylor Swift
Harry Styles and Taylor Swift, seen here during a Dec. 2012 outing, dated in the later part of 2012 until the first few days of 2013. (Backgrid)

Who can forget Harry’s romance with fellow singer Taylor Swift? The two apparently met and clicked at the 2012 Kids Choice Awards before they were later spotted on numerous outings together (often hand-in-hand) during the latter part of 2012, and even shared a kiss in New York’s Times Square on New Year’s Eve during the first minute of 2013. They apparently split just a few days into the new year, however, but Taylor put the memories of the relationship to good use in songs on her highly successful album 1989, which was released in 2014.

Many of the tracks on the musical masterpiece are reportedly about Harry, including “Style”, “Out of the Woods”, and “I Wish You Would”. It was also rumored that Harry’s song “Two Ghosts” from his self-titled debut solo album, which was released in 2017, was about their relationship.

Nicole Scherzinger

Nicole Scherzinger
Nicole Scherzinger, seen here leaving Hakkasan restaurant in Mayfair in 2014, reportedly briefly dated Harry in 2013. (MEGA)

The Sun reported that Harry and lead singer of the Pussycat Dolls, Nicole Scherzinger, hooked up in 2013. She was a judge on The X Factor when Harry appeared on it in 2010.

Kendall Jenner

Harry Styles, Kendall Jenner
Harry Styles and Kendall Jenner, who reportedly dated on and off from 2013 until 2016, are seen leaving Craig’s Restaurant in 2013. (Backgrid)

Harry was first spotted having dinner in Los Angeles with Kendall Jenner in Nov. 2013. They were rumored to be dating until a split in Feb. 2014, but they seemed to be on again by 2015 and were seen canoodling on a yacht during the first days of 2016. Although they never confirmed their relationship, Kendall’s sister, Khloe Kardashian, admitted she thought they were “dating” in a 2016 interview with ET Online.

“Do I think they’re dating? Yes,” she told the outlet. “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.”

Erin Foster

Erin Foster
Erin Foster, seen here at the 2017 Baby2Baby Gala, reportedly dated in 2014. (MEGA)

Harry and Erin Foster were first spotted getting pumpkins at a pumpkin patch in 2014 and dating rumors started swirling right away. The blonde beauty was known for being Gigi and Bella Hadid‘s (now ex) stepsister and her romance with Harry seemed to be short-lived.

Nadine Leopold

Nadine Leopold
Nadine Leopold, seen here at the CFDA Fashion Awards in 2019, reportedly dated Harry in 2014. (MEGA)

Nadine Leopold was reportedly the first Victoria’s Secret supermodel Harry ever dated. They were first seen together in Nov. 2014 and followed that outing up with some frozen yogurt dates, but by March 2015, things seemed to be over.

Sara Sampaio

Sara Sampaio
Sara Sampaio, seen here at the 2020 Vanity Fair Oscars party, reportedly dated Harry in 2015. (MEGA)

Harry was seen kissing other Victoria’s Secret model, Sara Sampaio, in New York in 2015. The Portuguese pretty lady was also spotted leaving Harry’s hotel the following day.

Georgia Fowler

Georgia Fowler
Georgia Fowler, seen here during a 2019 outing, reportedly dated Harry in 2015. (MEGA)

Harry and model Georgia Fowler, who is from New Zealand, reportedly dated for a brief time in Oct. 2015. He was seen playing the board game Scrabble with her in a Snapchat video she posted around the same time.

Tess Ward

Tess Ward
Tess Ward, seen here at an event at the Australia House at The Strand in London in 2018, reportedly dated Harry in 2017. (MEGA)

Harry reportedly had a brief relationship with chef and flood-blogger Tess Ward in the spring of 2017, but by June of the same year, things ended and she was soon seen back with her ex.

Camille Rowe

Harry Styles, Camille Rowe
Harry Styles and Camille Rowe, seen here after enjoying a dinner together in Hollywood in 2018, dated for a year. (MEGA)

The third Victoria’s Secret supermodel Harry was romantically linked to was Camille Rowe in 2017 and 2018. Fans first started speculating they were dating when a voice that sounded like Harry’s could be heard in one of the French-American beauty’s Instagram stories. They were seen together on multiple occasions but split up after a year. One of Camille’s voicemails can be heard in Harry’s heartbreaking song “Cherry” from his 2019 sophomore album, Fine Line.

Olivia Wilde

Harry Styles, Olivia Wilde
Harry Styles is seen visiting Olivia Wilde’s trailer on the set of the film ‘Don’t Worry, Darling’ in Nov. 2020. They were spotted holding hands at a wedding two months later. (Backgrid)

Harry’s latest rumored love interest is actress and director Olivia, who recently split from her husband of nine years, Jason Sudeikis. The two were seen holding hands at his agent’s wedding on Jan. 3 and were photographed with luggage at his Los Angeles home the next day. It’s not clear when the the stars first met, but Harry has been filming Don’t Worry, Darling, the latest movie directed by Olivia, over the past few weeks, so we can bet they’ve had time to get to know each other!

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The Queen Wipes Away Tears As She Arrives At Husband Prince Philip’s Funeral — See Photo

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queen elizabeth



Queen Elizabeth was emotional as she arrived at her late husband Prince Philip’s funeral at Windsor Castle. See all the photos.

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Brittany Matthews Shows Off Her Post-Baby Body In Fierce Orange Outfit 2 Months After Giving Birth

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Brittany Matthews Jackson Mahomes


Brittany Matthews came to slay in an orange blazer and mini skirt during a night out at Nobu. The new mama showed off her legs for days just two months after giving birth.

Hot mama alert! Brittany Matthews got gussied up for a night on the town in West Hollywood, and her post-baby style is sizzling. Just two months after giving birth to daughter Sterling Skye Mahomes, Brittany rocked a mini skirt and fitted blazer that showed off her already slim figure. The bright orange skirt suit, paired with a white tank top and ankle boots, gave off major mod vibes.

Brittany Matthews rocks an orange blazer while leaving dinner with future BIL Jackson Mahomes, 4/15/21 (HEDO/BACKGRID)

The new mom, 25, definitely deserved her April 15 dinner at Nobu. Accompanied by future brother-in-law Jackson Mahomes, she looked like she was having a blast. Brittany and her fiancé, NFL star Patrick Mahomes, 25, welcomed their baby girl into the world on February 21. They announced the joyous news on Instagram with a photo showing a tiny hand clutching Brittany’s finger in the hospital. The new mama wore a sparkly “Sterling” necklace.

The happy couple have shared plenty of adorable photos and videos of their first child on Instagram over the past two months. In early March, Brittany shared a cool video showing her baby bump progression during her trips to the gym. At the end, she’s cradling little Sterling on her flattened stomach. So cute!

Brittany Matthews Jackson Mahomes
Brittany Matthews and Jackson Mahomes’ fun night came two months after she gave birth (HEDO/BACKGRID)

Patrick was over the moon about becoming a first-time father. Just two weeks before Brittany gave birth, he expressed his joy in an interview with 610 Sports Radio Kansas City. “I mean really, anytime, I could be having a baby girl, and I’m super excited about that. It’s gonna be something special, and I’m excited for the journey of trying to find ways to better myself and become the best dad that I can be,” he said.

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​Lori Loughlin Delivers Food To Those In Need 3 Months After Prison Release — Pic

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​Lori Loughlin Delivers Food To Those In Need 3 Months After Prison Release — Pic


Lori Loughlin spent some time on April 14 delivering food with Project Angel Foods. See the latest photos of the former actress, who was released from prison at the end of December 2020.

Lori Loughlin kept a low-profile while volunteering in Los Angeles on April 14. The former Full House actress, 56, was spotted wearing a pair of blue jeans, a cream-colored sweater with 3/4 length sleeves, a face mask and baseball cap while out volunteering. Lori has been working with Project Angel Foods and delivering items to those in need, just over three months since her prison release.

Lori Loughlin is spotted volunteering at Project Angel Foods in Los Angeles after husband Mossimo Giannulli is freed from jail on April 14, 2021 [SplashNews.com].

This isn’t the first time that Lori has been spotted out and about, as she completes her 100 hours of community service that was designated along with her guilty plea. In fact, Lori was photographed driving her SUV in Calabasas, CA, on Thursday, April 8, just after her husband, Mossimo Giannulli, was released from prison and transitioned to home confinement on April 2. It’s been quite a whirlwind for the couple, who pled guilty in May 2020 to one count of conspiracy to commit wire and mail fraud by paying college admissions counselor Rick Singer over $500,000 in order to secure their daughters, Olivia Jade, 21, and Isabella Rose, 22, spots at the University of Southern California.

Lori served two months of her prison sentence, while Mossimo served five months. Along with serving time in prison, both Lori and Mossimo paid fines for their illegal actions. Lori paid $150,000 while Mossimo paid $250,000 in November 2020. Lori has been partnering with Project Angel Foods for some time, and was actually spotted delivering foods and services in early March.

Lori Loughlin was released from prison after serving a two-month sentence for involvement in the college admissions scandal. She is currently completing her 100-hour community service [Steven Senne/AP/Shutterstock].

Along with Lori and Mossimo settling back into their new normal, the couple’s daughters have also been repairing their own reputations. Olivia has been vocal about her part in the college admissions scandal, and for that Lori is proud. “Lori is so proud of Olivia for continuing to speak out,” a source shared EXCLUSIVELY with HollywoodLife in late March 2021.

“[Lori] wants to be able to speak out, but really wants to control the narrative and have Mossimo home [first],” the insider continued. “[But] she is closer with her daughters than ever right now.” Mossimo will begin completing his 250 hours of community service after April 17, a few short weeks after settling back at home.

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