Since he is one of the biggest music stars of his generation, millions of fans are fascinated by every aspect of Harry Styles' personal life. A perfect example of that is the fact that Styles' fans want to understand his bond with Shania Twain.

What some people may forget at times is that Styles was a normal person with a modest job before he became a superstar. Once Styles' ascent to fame and fortune began, the pop star kept his feet close to the ground in a completely unexpected way.

Why Did Harry Styles Live With An Orthodox Jewish Family For Months?

Despite orthodox Jews only accounting for a fraction of the Jewish population on the planet (which is approximately 16 million), there are about 2 million of them. Still, very few people outside of the ethnoreligious group know what their lifestyle consists of. Orthodox Jews have to follow a litany of ancient laws that have symbolic significance to the teachings of the Torah and its related texts.

Harry Styles looking at the crowd at one of his concerts
Harry Styles performing onstage
Via: Instar

While there isn't enough room here to list the rules that orthodox Jewish people follow here, suffice it to say that it is a very conservative lifestyle. With that in mind, it is a massive understatement to say that most music stars would feel extremely stifled if they lived with an orthodox Jewish family.

Back when Harry Styles was first becoming a huge star, he spent twenty months living with an orthodox Jewish family. That fact begs two obvious questions, why did Styles move in with the family, and why did he stay so long?

When Harry Styles was a child, his family moved to an English village called Holmes Chapel. When Styles has talked about his childhood in the past, he has expressed how fortunate he was to grow up with such a loving and supportive family. However, living in a village that had a population of just over 5,600 as of 2011 didn't make a lot of sense after Styles' music career began.

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Once Styles auditioned for The X Factor and began competing on the show, he needed to be located in the nearby area. As a result, Styles made the arrangements to move nearby the show's studio at the time which was located in London, England.

Unfortunately for Styles, the home he arranged to stay in had to have some work done to it before the singer could move in. That left Styles looking for a nearby place to live for a couple of weeks as he waited for the home to be ready.

As Styles began the filming process for The X Factor, he met and befriended a man named Ben Winston who worked on the show. After Winston wound up becoming a mentor of sorts to Styles, he learned the singer needed somewhere to stay briefly.

Harry Styles and Ben Winston having fun backstage
Harry Styles with his friend Ben Winston who let the singer live with him for 18 months
Via: Instagram

Obviously a kind-hearted person and a good friend to Styles, Ben Winston let the singer stay with him and his wife Meredith Winston. By the time Styles stayed with them, the Winstons hadn't had any children together, but they definitely were a family already.

Rolling Stone Magazine would later report on Styles' time staying with the Winstons. According to the legendary magazine's article, the living situation that was supposed to be short-lived kept being extended.

After the originally planned two weeks were up, work on Styles' home wasn't complete yet, so he stayed with the Winstons. From there, a slew of reasons came up for Styles to continue staying with the Winstons when he was supposed to move out.

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Ultimately Styles lived in the Winston's attics for more than a year and a half. According to Rolling Stone, it certainly doesn't sound like Styles had the most comfortable sleeping situation when he stayed with the Winstons, at least at first. When Styles first began staying in the Winston's attic, he took a mattress up there to sleep on.

Rolling Stone spoke to Ben Winston about the time Styles stayed with him and his wife. According to Ben Winston, Styles was living with the couple as his life changed forever and nobody knew it at the time.

“Those 20 months were when they went from being on a reality show, X Factor, to being the biggest-selling artists in the world. That period of time, he was living with us in the most mundane suburban situation. No one ever found out, really. Even when we went out for a meal, it’s such a sweet family neighborhood, no one dreamed it was actually him."

Ben Winston and Meredith Winston at the Emmy Awards
Ben Winston and Meredith Winston on the red carpet
Via: Instagram

As amazing as it is that Styles stayed with the Winstons at such a pivotal moment in his life, there is something else to consider. The vast majority of couples in the world wouldn't allow someone they'd just met live with them for twenty months.

Based on what Ben Winston told Rolling Stone, he and his wife seem to adore Styles and were sad when he finally moved out. "But he made our house a home. And when he moved out, we were gutted.”

Is Harry Styles Still Close With Ben Winston And Meredith Winston?

Throughout the history of talent shows like The X Factor, the vast majority of people who've competed on them have quickly left the spotlight. With that in mind, it should go without saying that when Ben Winston and Meredith Winston let Harry Styles stay with them, it was purely an act of kindness.

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Given that Styles is so successful that he spends months touring the world, it seems safe to assume that he doesn't get to be with the Winstons too often. It also has to be noted that the couple also has a busy lifestyle too. Ben Winston served as The Late Late Show with James Corden's executive producer from 2015 until 2023.

While Styles and the Winstons can only be together so much, it still is very clear they have a close bond.

There have been many pieces of evidence that point to how close Styles is with the Winstons. For example, Styles seems to semi-regularly show his love for the Winstons on social media as he often posts about Jewish holidays even though the pop star isn't Jewish.

Harry Styles waving while he performs
Harry Styles performing onstage
Via: Instar

In June 2023, Styles and the Winstons all made their love for each other clear. When Styles performed at Wembley Stadium on a Saturday, The Winstons walked miles to the venue, so they could see their friend perform while still honoring Shabbat.

According to a reporter for Jewish Chronicle named Tash Mosheim, Styles took time out of his concert to thank the couple for how hard they worked to be there.

Easily the most obvious piece of evidence that the Winstons and Styles love each other is the role the pop star now plays in their family. After Styles moved out of their home, the Winstons went on to have three children. When the couple's daughter Ruby Winston was born, Styles became her godfather. Styles would later record Ruby Winston saying "Come on, Harry, we want to say goodnight to you" and use his goddaughter's voice in his song "As It Was".