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In honor of Harry Styles’ 28th birthday on Feb. 1, 2022, Wonderwall.com rounded up all the celebs who’ve famously dated older women over the years, starting with the former One Direction singer… Harry has been in a serious relationship with Olivia Wilde, who’s 10 years his senior, since late 2020. The duo connected when she directed the psychological thriller “Don’t Worry Darling,” in which he has a starring role. It’s not the first time the “Watermelon Sugar” chart-topper has romanced an older woman, though… He even said back in 2012 that he’s open to dating anyone his mom’s age or younger! (She was reportedly born in 1967.)
Keep reading to get the scoop on the older woman Harry dated when he was just a teenager, then read on for more celebs who’ve had older gal pals…
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Harry Styles was just 17 when he started seeing English actress and TV host Caroline Flack, who was 31 at the time. They connected in 2011 through their mutual ties to the British version of “The X Factor” — the reality TV show on which One Direction got their start that Caroline later hosted after initially presenting its companion show, “The Xtra Factor.” Years later, Caroline, who died in early 2020, said of her brief romance with the singer, “I’ve never felt I was much older than Harry anyway. I still feel 18 and probably act that way half the time.”
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Harry Styles isn’t the only former member of One Direction who famously romanced an older woman… Liam Payne first connected with British singer and TV personality Cheryl Cole in 2008 when he auditioned for the British version of “The X Factor” while she was serving as a judge. At the time, he was 14 and she was about 25. Fortunately, it would be another seven years before things between them turned romantic. They were an item from 2015 to 2018 and even welcomed a son, Bear, in 2017.
RELATED: Celebs who dated their crushes
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Pete Davidson and Kim Kardashian practically broke the Internet when they started dating in late 2021 after she hosted an episode of “Saturday Night Live.” There’s a 13-year age gap between the comedian and the mother of four. But it wasn’t Pete’s first experience with an older woman…
RELATED: All the famous beauties Pete has loved and lost over the years
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A few years before Pete Davidson and Kim Kardashian made waves, the “Saturday Night Live” star had a brief but noteworthy fling with Kate Beckinsale. For the three months between January 2019 and April 2019, the age-mismatched duo (there’s a 20-year gap between them) were Hollywood’s hottest “it” couple.
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Nick Jonas’s missus, Priyanka Chopra, is a decade older than him. They exchanged vows in late 2018 following a whirlwind courtship of less than a year and welcomed their first child together in early 2022.
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Hugh Jackman is 13 years younger than his wife of more than 25 years, Deborra-lee Furness. They first connected on the set of the 1995 Australian miniseries “Correlli” — his first big gig as an actor fresh out of drama school — and tied the knot in 1996.
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Jason Momoa’s estranged wife, Lisa Bonet, is 11 years older than him. The “Aquaman” actor and the former “The Cosby Show” star revealed in January 2022 that they’d separated after more than four years of marriage and more than 15 years as a couple. (They got together in 2004 when he was just 25.)
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Portia de Rossi’s wife, Ellen DeGeneres, is 15 years her junior. The “Arrested Development” alum and the comedian tied the knot in 2008 following a courtship of about four years.
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“Parks and Recreation” alum Nick Offerman is 12 years younger than his wife, “Will & Grace” actress Megan Mullally. They first connected in 2000 while co-starring in a production of “The Berlin Circle,” got engaged in 2002 and quietly exchanged vows the following year.
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There’s a 32-year age gap between Sarah Paulson and long-term love Holland Taylor. The “American Horror Story” actress and the former “Two and a Half Men” star were first publicly linked in 2015.
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Aaron Taylor-Johnson met his wife, filmmaker Sam Taylor-Johnson, in 2008 when he auditioned to play a young version of John Lennon in her feature film directorial debut, “Nowhere Boy.” He was 18 or 19 at the time and she was 42. The duo got engaged a year after they met, welcomed two daughters and tied the knot in 2012.
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Snow Patrol rocker Johnny McDaid is 12 years younger than off-and-on love Courteney Cox. They reportedly met through mutual pal Ed Sheeran in 2013, got engaged in 2014, split in 2015 and reconnected in 2016. They’ve been going strong ever since, though they’re no longer engaged.
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If the rumors are true, The Weeknd and Angelina Jolie quietly started dating in mid-2021. The Oscar-winning mother of six is 15 years older than the chart-topping musician.
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Ashton Kutcher’s ex-wife, Demi Moore, is 16 years older than him. They started dating in 2003 when he was 25 and tied the knot two years later, but it wasn’t meant to be: They split in 2011 and finalized their divorce in 2013. Two years later, he married second wife Mila Kunis, who’s five years his junior.
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Tokio Hotel rocker Tom Kaulitz is 16 years younger than his wife, German supermodel Heidi Klum. They started dating in early 2018 when he was 28 and she was 44.
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Dwyane Wade is nine years younger than his wife, “Bring It On” star Gabrielle Union. The retired basketball player and the actress reportedly met in 2007, though it’s unclear when exactly things between them turned romantic. They married in 2014.
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Professional baseball player Cole Tucker is eight years younger than his girlfriend, Vanessa Hudgens. The duo celebrated their first anniversary in late 2021.
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There’s a 10-year age gap between Spanish professional soccer player Gerard Piqué and his long-term partner, Shakira. The duo first connected in 2010 when he was in his early 20s. They’ve since welcomed two sons, though the Colombian singer has made it clear they have no plans to tie the knot.
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Let’s be honest: Sam Asghari might not be famous if he hadn’t started dating Britney Spears, who’s about 13 years his senior, after they connected on the set of her 2016 “Slumber Party” music video. Thanks to their long-term romance, the aspiring actor, who popped the question in September 2021, is now a celeb in his own right.
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