Who dated Olivia Wilde?
Jason Sudeikis dated Olivia Wilde from until . The age gap was 8 years, 5 months and 21 days.
Harry Styles dated Olivia Wilde from until . The age gap was 9 years, 10 months and 22 days.
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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Daniel Jason Sudeikis ( suu-DAY-kiss; born September 18, 1975) is an American actor, comedian, screenwriter, and producer. In the 1990s, he began his career in improv comedy and performed with ComedySportz, iO Chicago (Improv Olympic), and The Second City. In 2003, Sudeikis was hired as a writer for the NBC sketch comedy series Saturday Night Live, and later spent nine seasons as a cast member from 2005 to 2013, playing Joe Biden and Mitt Romney, among others.
From 2020 to 2023, he co-created and played the title role in the Apple TV+ sports comedy series Ted Lasso, which earned him four Primetime Emmy Awards and two Golden Globe Awards. He was also one of the leading cast members in The Cleveland Show (2009–2013). Sudeikis has also acted in recurring roles in the comedy series 30 Rock (2007–2010), It's Always Sunny in Philadelphia (2010–2011), Eastbound and Down (2012), Portlandia (2011–2014), and The Last Man on Earth (2015–2018).
He had leading film roles in the comedies Horrible Bosses (2011) and its sequel, Horrible Bosses 2 (2014), and We're the Millers (2013), as well as the acclaimed independent films Drinking Buddies (2013), Sleeping with Other People (2015), and Colossal (2016), and supporting roles in Alexander Payne's Downsizing (2017) and Olivia Wilde's Booksmart (2019). He has also acted in voice roles for Epic (2013), The Angry Birds Movie (2016) and The Angry Birds Movie 2 (2019), and Next Gen (2018).
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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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