Who Celebrities Dated Before They Met Their Other Half

Some celebrity couples look so suited to each other that it seems they’ve always been together, even though many of them have come a long way to find their soulmates. Some previous celebrity romances have long been forgotten, while others may not have been known about at all, even by their loyal fans. But it’s always interesting to see who our idols dated before they found The One.

Ryan Reynolds and Blake Lively

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From 2002 to 2007, Reynolds was in a relationship with singer and actress Alanis Morissette. The couple even announced an engagement, but never got married. Lively, on the other hand, dated her on-screen partner Penn Badgley during the filming of Gossip Girl.

Ashton Kutcher and Mila Kunis


Kutcher was officially married to Demi Moore from 2005 to 2013. However, the couple actually broke up in 2012 because Kutcher had already started dating his on-set partner of That ’70s Show, Mila Kunis. Before getting together with her current husband, Kunis was in a relationship with Macaulay Culkin; the pair stayed friends after the breakup.

Justin Timberlake and Jessica Biel

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One of Justin Timberlake’s longest, and most high-profile relationships was with Britney Spears. The Mickey Mouse Club alumni dated until 2002. Meanwhile, Jessica Biel was in a relationship with her partner on set in the film London, Chris Evans.

Norman Reedus and Diane Kruger

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The longest and most serious relationship that The Walking Dead star Reedus had was with supermodel Helena Christensen. It lasted for five years. Despite having a son together, they were never married and remained friends after their breakup. Diane Kruger’s longest relationship was with actor Joshua Jackson, although their romance didn’t lead to a wedding either.

Michael Douglas and Catherine Zeta-Jones

In 1977 Douglas married Diandra Luker, the 19-year-old daughter of an Austrian diplomat. In this marriage, the actor had a son, Cameron. Catherine Zeta-Jones dated TV presenter John Leslie in the early 1990s.

Blake Shelton and Gwen Stefani

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During a recording session in 2005, Shelton met singer Miranda Lambert, whom he later married and stayed with until 2015. Stefani, on the other hand, had her longest and most high-profile relationship with the guitarist and lead singer of Bush, Gavin Rossdale. They met back in 1995 and divorced only in 2016.

Chris Hemsworth and Elsa Pataky

Before his romance with Elsa Pataki, Hemsworth dated actress and model Isabel Lucas, who he met on the set of the series Home and Away. Pataki was in a relationship with Adrien Brody, which lasted three years.

Taika Waititi and Rita Ora

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In 2011, Waititi married New Zealand film producer Chelsea Winstanley. The marriage, in which the couple had two daughters, lasted until 2018. As for Rita Ora, her most famous boyfriend was DJ Calvin Harris.

A$AP Rocky and Rihanna

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In 2013, A$AP Rocky had a relationship with model Chanel Iman. They even got engaged fairly quickly, but never got married. Rihanna’s longest relationship was with Drake. They repeatedly broke up and got back together again.

Jesse Plemons and Kirsten Dunst

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Before meeting his current wife, Plemons was in a long-term relationship with actress Courtney Peterson. Kirsten Dunst, in turn, had a love affair with Jake Gyllenhaal, who she met thanks to his sister, Maggie Gyllenhaal. They dated and lived together until 2004.

Swizz Beatz and Alicia Keys

Swiss Beatz’s longest and most serious relationship was with singer Mashonda Tifrere, whom he began dating in 1998, and was married to until 2010. Alicia Keys, meanwhile, was in a relationship for over 10 years with her long-time friend and co-author of her songs Kerry Brothers Jr.

Justin Long and Kate Bosworth

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For three years, from 2007 to 2010, Justin Long was in an on-again-off-again relationship with Drew Barrymore. Long’s current partner, actress Kate Bosworth, dated director Michael Polish. The pair had even announced an engagement, but it went no further than that.

Tom Pelphrey and Kaley Cuoco

Prior to his relationship with his current partner, Pelphrey was with actress Gina Tognoni. They starred together on the soap opera Guiding Light. As for Cuoco, the star had a relationship with fellow The Big Bang Theory actor Johnny Galecki.

Tom Holland and Zendaya

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In the 2010s, Tom Holland had a romance with his childhood sweetheart Elle Lotherington. Meanwhile, around the same time, Zendaya allegedly had a relationship with singer and actor Trevor Jackson. They worked together on the TV series K.C. Undercover.

Ian Somerhalder and Nikki Reed

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The Vampire Diaries star Ian Somerhalder dated his on-screen partner Nina Dobrev from 2010 to 2013. Prior to her relationship with Somerhalder, Nicki Reed was with singer and American Idol alumnus Paul McDonald. They married in 2011, though their marriage didn’t last long.

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