Who dated Harry Styles?
Caroline Flack dated Harry Styles from until . The age gap was 14 years, 2 months and 23 days.
Taylor Swift dated Harry Styles from until . The age gap was 4 years, 1 months and 19 days.
Kendall Jenner dated Harry Styles from until . The age gap was 1 years, 9 months and 2 days.
Nicole Scherzinger dated Harry Styles from until . The age gap was 15 years, 7 months and 3 days.
Camille Rowe dated Harry Styles from until . The age gap was 4 years, 0 months and 25 days.
Olivia Wilde dated Harry Styles from until . The age gap was 9 years, 10 months and 22 days.
Harry Styles

Harry Edward Styles (born 1 February 1994) is an English singer, songwriter, and actor. His showmanship, artistry, and flamboyant fashion have had a significant impact on popular culture.
Styles's musical career began in 2010 as part of One Direction, a boy band formed on the British music competition series The X Factor after each member of the band had been eliminated from the solo contest. They became one of the best-selling boy bands of all time before going on an indefinite hiatus in 2016. Styles released his eponymous debut solo album through Erskine and Columbia Records in 2017. It debuted at number one in the UK and the US and was one of the world's top-ten best-selling albums of the year, while its lead single, "Sign of the Times", topped the UK Singles Chart.
His second album, Fine Line (2019), debuted atop the US Billboard 200 with the biggest ever first-week sales by an English male artist. Its fourth single, "Watermelon Sugar", topped the US Billboard Hot 100. Styles's widely acclaimed third album, Harry's House (2022), broke several records and received the Grammy Award for Album of the Year. Its lead single, "As It Was", became the number-one song of 2022 globally, according to Billboard.
Styles has received various accolades, including six Brit Awards, three Grammy Awards, two Ivor Novello Awards, three American Music Awards, and four MTV Video Music Awards. Fine Line and Harry's House were both included on Rolling Stone's list of "The 500 Greatest Albums of All Time". Styles's film roles include Dunkirk (2017), Don't Worry Darling (2022), and My Policeman (2022). Wearing a blue Gucci dress, he became the first man to appear solo on the cover of Vogue. Styles contributes to various charities and advocates for gender, racial, and LGBTQ equality.
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Caroline Louise Flack (9 November 1979 – 15 February 2020) was an English television presenter. Flack grew up in Norfolk and took an interest in dancing and theatre while at school. She began her professional career as an actress, starring in the comedy sketch show Bo' Selecta! (2002), and went on to present various ITV2 shows including I'm a Celebrity...Get Me Out of Here! NOW! (2009–2010) and The Xtra Factor (2011–2013).
In 2014, Flack won the twelfth series of BBC's Strictly Come Dancing and was praised for achieving a record perfect score in the final. The following year, she began presenting The X Factor, replacing the long-standing presenter Dermot O'Leary, and Love Island, hosting until her resignation in December 2019 after being arrested for assault allegations.
On 15 February 2020, aged 40, Flack was found dead at her home in North East London; in August, a coroner's inquest recorded a verdict of suicide.
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Taylor Swift

Taylor Alison Swift (born December 13, 1989) is an American singer-songwriter. Her autobiographical songwriting, musical reinventions, and touring records have made her a cultural icon of the 21st century. She is the highest-grossing touring musician, the wealthiest female musician, and one of the best-selling music artists of all time.
Swift signed to Big Machine Records in 2005 and debuted as a country singer with the albums Taylor Swift (2006) and Fearless (2008). The singles "Teardrops on My Guitar", "Love Story", and "You Belong with Me" found crossover success on country and pop radio formats. Speak Now (2010) expands on her country pop sound with rock influences, and Red (2012) incorporates a pop-friendly production. She recalibrated her artistic identity from country to pop with the synth-pop album 1989 (2014) and the hip-hop-imbued Reputation (2017). Her number-one singles on the Billboard Hot 100 in the 2010s decade include "We Are Never Ever Getting Back Together", "Shake It Off", "Blank Space", "Bad Blood", and "Look What You Made Me Do".
After signing with Republic Records in 2018, Swift re-recorded four studio albums as a countermeasure to the dispute over her Big Machine album masters. Her subsequent releases include the eclectic pop album Lover (2019), the indie folk albums Folklore and Evermore (both 2020), and the minimalist synth-pop albums Midnights (2022) and The Tortured Poets Department (2024). Her Eras Tour (2023–2024) is the highest-grossing tour of all time, and she has garnered seven Billboard Hot 100 number-one singles in the 2020s decade: "Cardigan", "Willow", "All Too Well (10 Minute Version)", "Anti-Hero", "Cruel Summer", "Is It Over Now?", and "Fortnight".
Swift is the first artist to have seven albums that each sell one million copies first-week in the US and has been recognized as the IFPI Global Recording Artist of the Year five times. Publications such as Rolling Stone and Billboard have ranked her among the greatest artists of all time. She is the first individual from the arts to be named Time Person of the Year (2023). Her accolades include 14 Grammy Awards (including a record four Album of the Year wins); she is the most-awarded artist of the American Music Awards, the Billboard Music Awards, and the MTV Video Music Awards. A subject of extensive media coverage, she has a global fanbase called Swifties.
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Kendall Jenner

Harry Styles

Nicole Scherzinger

Nicole Prascovia Elikolani Scherzinger ( SHUR-zing-ər; née Valiente; born June 29, 1978) is an American singer, songwriter, dancer, actress, and television personality. She was a member of the girl group and dance ensemble the Pussycat Dolls between 2003 and 2010. With two albums and over 55 million records sold worldwide, the Pussycat Dolls became one of the world's best-selling female groups of all time.
Born in Honolulu, Hawaii, and raised in Louisville, Kentucky, Scherzinger began acting at the age of 14 and studied musical theatre at Wright State University. In pursuit of a musical career, Scherzinger dropped out of college and toured with the American rock band Days of the New before finding mild success with Eden's Crush, a girl group created through The WB's talent competition show Popstars. After taking on minor acting roles, Scherzinger became the lead singer of the Pussycat Dolls. Scherzinger carved out a solo career outside the group; her debut album, Her Name is Nicole, was shelved due to insufficient commercial response from its promotional singles. However, her debut album was released as Killer Love (2011)—which was supported by the singles "Right There" (featuring 50 Cent), "Poison" and "Don't Hold Your Breath"—followed by its sequel, Big Fat Lie (2014). Both albums failed to chart domestically, although they found moderate success on international charts.
Scherzinger has served as a judge on television talent shows, including The Sing-Off (2009–2010), The X Factor US (2011), The X Factor UK (2012–2013, 2016–2017), Australia's Got Talent (2019), and The Masked Singer (2019–2023). In 2010, she competed on the television dancing competition show Dancing with the Stars, in which she won. Other work during this period includes her theatrical roles in Cats (2014) and Sunset Boulevard (2023–2025), as well as roles in the Disney animated film Moana (2016), the ABC film Dirty Dancing (2017), and the NBC special Annie Live! (2021).
During her career, Scherzinger has received nominations for a Grammy, two Laurence Olivier Awards and a Tony Award. She won the 2024 Laurence Olivier Award for Best Actress in a Musical for her performance as Norma Desmond in the 2023 West End revival of Sunset Boulevard and received the Tony Award for Best Actress in a Musical in 2025 when the show transferred to Broadway in 2024. Her other ventures include clothing lines and a fragrance, as well as serving as an ambassador for the Special Olympics and as a supporter of UNICEF UK.
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Camille Rowe
Camille Chrystal Pourcheresse, known professionally as Camille Rowe, is a French-American model and actress.
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Olivia Wilde

Olivia Wilde (born Olivia Jane Cockburn, KOH-bərn, March 10, 1984) is an American actress and director. She played Remy "Thirteen" Hadley on the medical-drama television series House (2007–2012), and appeared in the action films Tron: Legacy (2010) and Cowboys & Aliens (2011), the romantic drama film Her (2013), the comedy film The Incredible Burt Wonderstone (2013), and the horror film The Lazarus Effect (2015). She made her Broadway debut playing Julia in 1984 (2017).
Wilde made her directorial debut with the teen comedy film Booksmart (2019), which received critical acclaim and won the Independent Spirit Award for Best First Feature. She directed the thriller film Don't Worry Darling (2022), which she also starred in.
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