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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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Liz Cheney: 5 Things About GOP Rep. Ousted From House Leadership After Speaking Out Against Trump

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Liz Cheney


Rep. Liz Cheney is no longer Chair of the House Republican Conference after her criticism of Trump and his ‘Big Lie’ about election fraud. Learn more about her.

Rep. Liz Cheney (R-WY) was just ousted from a top leadership position in the House by her own party. Cheney isn’t letting it go. The three-term congresswoman, 54, is lashing out at her fellow lawmakers who are still bowing at former President Donald Trump‘s feet and warning them that they’ll doom our democracy. Here’s what else you need to know about Rep. Cheney:

1. She Was The Chair of the House Republican Conference

Cheney held the third-highest leadership position for Republicans in the House of Representatives since 2019. Her “competency” came into question when she started vocalizing her criticism of former President Donald Trump for his repeated “Big Lie” about election fraud and his role in the Capitol siege. After Cheney voted with Democrats to impeach Trump in January, a pro-Trump faction of the House, including Minority Speaker Kevin McCarthy (R-CA), called for her removal from the chairmanship. A House committee voted behind closed doors to oust Cheney on May 12.

2. She Warned Fellow Reps. About Trump In Her Final Speech

During the closed-door meeting to oust Cheney from House leadership, a source told ABC News that Cheney urged her colleagues not to let Trump make the GOP “complicit in his efforts to unravel our democracy.” Cheney said:

“Our nation needs this Republican Party as a strong party based on truth so we can shape the future. To do that, we must be true to our principles and to the Constitution. We cannot let the former president drag us backward and make us complicit in his efforts to unravel our democracy. Down that path lies our destruction, and potentially the destruction of our country. If you want leaders who will enable and spread his destructive lies, I’m not your person, you have plenty of others to choose from. That will be their legacy.”

3. She Has Support From Both Prominent Democrats & Republicans

Democratic House Speaker Nancy Pelosi said after the ouster, “Congresswoman Liz Cheney is a leader of great courage, patriotism and integrity. Today, House Republicans declared that those values are unwelcome in the Republican party. The Republican denial of the truth presented by Congresswoman Cheney is reflected in their denial of the need to seek the truth in a January 6th commission and to repair the damage of January 6th with a security supplemental immediately.”

4. Her Father Is Former VP Dick Cheney

Rep. Cheney is the eldest daughter of Dick Cheney, who served as vice president under former President George W. Bush from 2001 to 2009. In the House of Representatives, she holds the same seat her father once occupied as Wyoming’s congressman from 1979 to 1989.

Rep. Liz Cheney speaks to reporters after she was voted out of her House leadership role, 5/12/21 (Shutterstock)

5. Some Think She Could Lead A 3rd Party

With Trump’s grasp on the Republican party now clearer more than ever, some politicos are wondering if a fractured GOP could lead to a major third political party. With Cheney the loudest and highest-ranking opponent of Trump, she would be a natural leader. She almost outright vowed to do that in her last speech before her May 12 ouster: “I promise you this, after today, I will be leading the fight to restore our party and our nation to conservative principles, to defeating socialism, to defending our republic, to making the GOP worthy again of being the party of Lincoln.”



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‘The Masked Singer’ Preview: The Russian Dolls Reveal A New Clue — Watch

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Russian Dolls


The Russian Dolls read a brand-new clue in this EXCLUSIVE preview of ‘The Masked Singer’ quarterfinals, and guest panelist Rob Riggle is convinced he knows their identities.

The quarterfinals have arrived on The Masked Singer, and the Russian Dolls will take the stage once again during the May 12 episode. After their performance, a new clue is revealed by “mail” sent by the biggest fan in this EXCLUSIVE preview. When host Nick Cannon opens up the mailbox, there’s another mailbox inside, a nod to the Russian Dolls.

One of the Russian Dolls reads the letter inside the second mailbox. “I was a fan of you individually, but when I saw you band together in person — wow! Like I can’t even. Love you to the moon and back again,” the letter says.

The Russian Dolls during the May 12 episode. (FOX)

Guest panelist Rob Riggle doesn’t believe he even needs this clue to guess the identities of the Russian Dolls. “Clues are for suckers. I don’t need them,” he says. He thinks he knows exactly who the Russian Dolls are.

“Bet this all day. Bet it twice on Sunday. That’s Devo,” Rob says. Devo is a rock band that rose to fame in the 1970s and 1980s. The band is best known for their hit song “Whip It.”

Nick isn’t convinced that Rob is right on this one. “Ken, this really is your friend,” Nick jokes. This makes Ken Jeong cackle.

The Russian Dolls
The Russian Dolls during their quarterfinals performance. (FOX)

The Russian Dolls changed the game from their very first performance of “The Man in the Mirror” by Michael Jackson. One Russian Doll started out singing the song, but a second Russian Doll later revealed himself during the performance. The Russian Dolls debuted a third member in the wildcard round. They’ve been stealing the show from the start.

The final 5 of season 5 are Russian Dolls, Chameleon, Black Swan, Piglet, and Yeti. At the end of the May 12 episode, one of the masked singers will be eliminated. The rest will move on to the season 5 semi-finals. The Masked Singer season 5 airs Wednesdays at 8 p.m. on FOX.

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‘Siesta Key’: Chloe Reveals Why She Left Season 4 After Filming Took A Toll On Her Mental Health

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siesta key


Previews for season 4 of ‘Siesta Key’ show Chloe Trautman announcing that she’ll be leaving the show in the middle of filming, and she dished all about it in our EXCLUSIVE interview.

“I’m at a point where I really don’t want to be a part of this anymore,” Chloe Trautman says in the trailer for season 4 of Siesta Key. “Farewell everyone.” While the details surrounding Chloe’s unexpected departure are still vague, she dished more about the decision in an EXCLUSIVE interview with HollywoodLife. In the months leading up to filming, Chloe underwent an extreme mental and physical lifestyle change. She lost 50 pounds and cut “toxic” people out of her life. However, when filming for Siesta Key began again in Nov. 2020, she noticed that the “old Chloe” was starting to come back.

“In that environment, I have always been the ‘old Chloe,’ and it was like oil and water mixing filming and the new me,” she explained. “Well, I don’t like to say ‘new me,’ I like to say ‘true me.’ This season, you really see that battle of me trying to stay the course with the internal work that I’ve done. But I’m not perfect and I definitely have some bumps this season. Overall, I’m really proud of myself for putting myself out there and putting my mental health first. I think, more than ever, that’s such an important message to send — no matter what you’re doing in your life, if you’re placing yourself in an environment that’s not for your highest good, walk away from it. I’m just proud that I’ll represent that this season.”

Chloe did make the difficult decision to walk away. She said that the lack of support from her friends, who were skeptical about her transformation, was what ultimately led to the decision. “They weren’t as supportive as I think they could’ve been,” Chloe admitted. “Understandably, they were skeptical — they were wondering if this was just a phase. But for me, it just really built up. Every week, all the cast parties we’d go to, it would just build up over and over and over again. It just got to a point where I was like, ‘Alright, guys, stop trying to tear me down.’ When I didn’t feel like I had enough support from my friends and cast and production, I took a big step back.”

Luckily, it was the right decision, and Chloe told that it was “extremely necessary” for her. “I feel like I did the most work on myself in that time when I took a step back,” she revealed. “To me, in your true power, you should be able to place yourself in any environment and still stand true to who you are.”

The cast of season 4 of ‘Siesta Key’. (MTV)

Chloe also dished about the “breaking point” that led her to transform her lifestyle and become the person who she is today. “[In March 2020], our friend group went to Aspen and I was 50 pounds heavier than I am right now,” she explained. “I was skiing down a mountain and I was so out of shape, and I ended up falling and really hurting myself. It was in that moment that I cried out to God for help. Then, I went through a breakup with my ex-boyfriend of almost four years and my grandmother, who passed away, came to me and spoke to me on her birthday in June. My life just changed. The right people started to come into my life. I stopped drinking. I stopped partying. I really stepped back from any toxic environment or friendships I was in, too.”

Now, Chloe is “really excited” to show Siesta Key viewers the new version of herself. “I can’t wait to show people how, when you heal yourself, it’s truly the greatest thing you can ever do,” she gushed. “And how important it is to take time for yourself and mental health and meditating and all those beautiful things.” Siesta Key returns on May 12 at 8:00 p.m. on MTV.



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