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Justin Timberlake’s Dating History: From Cameron Diaz to Jessica Biel and More

by Iyzklez
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Ladies’ man! Justin Timberlake paired up with a slew of A-listers before settling down with wife Jessica Biel in 2012. The singer counts Britney Spears, Cameron Diaz, Jenna Dewan, Fergie, Alyssa Milano and more famous females as his exes.

Timberlake and Biel tied the knot in October 2012 after dating on and off for five years. The couple welcomed son Silas in April 2015.

Despite his committed relationship, the actor’s love life continues to make headlines. Timberlake and his Palmer costar Alisha Wainwright caused a frenzy in November 2019 when they were spotted holding hands in New Orleans. A source told Us Weekly at the time that the two were “just friends.”

“Nothing remotely romantic is going on with Justin and Alisha,” an insider said, while another source added: “They are like brother and sister. They are definitely not hooking up.”

Wainwright’s rep also denied that there was any “validity to this speculation.”

Before his PDA scandal, Timberlake often gushed about his marriage to Biel. “My partner in this thang called life… you are the most wonderful human I have ever met,” he wrote via Instagram in March 2019. “You make me smile, laugh, and love life more than I knew I could. I cherish every moment with you and can’t wait to spend so many more years doing the same… but, new.”

The Grammy winner shared similar sentiments in his 2018 book, Hindsight. “She’s become a huge influence in my life, and I have such admiration for her. … She’s a very good writer. She’s a poet. She’s a tremendous actor. She’s funny,” he raved. “She changed me. She changed my life.”

Timberlake went on to note that Biel is “a different person” than when they met. “We should say ‘I will’ instead of ‘I do’ when we get married because people constantly change, both physically and mentally,” he explained. “I’ve watched my wife change. I’ve watched her body change. It’s a temple. It should be worshipped. It should be marveled at. I’m fascinated by her. … I wake up and roll over and look at her, and I’m inspired.”

Scroll to revisit the crooner’s dating history!


Timberlake and the Black Eyed Peas member briefly dated from 1996 to 1997. “He was 16 and I was 23,” she told Australia’s Courier Mail. “It was before he got real heavy with Britney.”

Britney Spears

Young love! The former ‘NSync member and Spears romanced each other after appearing on The Mickey Mouse Club. They were an item from 1999 to 2002.

Jenna Dewan

Timberlake began seeing his backup dancer after his split from Spears. Dewan confirmed her relationship with the “SexyBack” singer during a May 2017 appearance on Watch What Happens Live With Andy Cohen. “We dated, not that long,” she explained. “We were like friends … that dated.”

Alyssa Milano

The Charmed alum dated the Social Network star in 2002. Years later, Milano confessed she was rooting for Spears and Timberlake to work things out. “They were super cute, super in love,” she told Entertainment Tonight in September 2015. “They just seemed like the perfect match!”

Cameron Diaz

The actress and Timberlake were together from 2003 to 2006. The exes later reunited onscreen in 2011’s Bad Teacher. “Justin and I have always had a good laugh together, and to make a movie where we get to have a laugh together, and there really was no one else who was more perfect for this part,” Diaz told Us in March 2011, adding: “It really wasn’t a big deal, we had a great time and did the job, and we do what all actors do afterward: We all go our separate ways.”

Jessica Biel

Biel and the “Cry Me a River” crooner made their relationship public in January 2007. They split in March 2011 before reconciling the following July. The pair got engaged in January 2012 and exchanged vows in October 2012. They are parents of son Silas, who was born in April 2015.

Olivia Munn

Us broke the news that Timberlake cheated on Biel with Munn in September 2010. His rep denied the allegations at the time.

Olivia Wilde

The Trolls star was linked to the Booksmart director in April 2011 during a break from the 7th Heaven alum. “They were obviously a couple or on a date,” an insider told Us after Timberlake and Wilde were spotted dancing and flirting in L.A.

Ashley Olsen

Us reported in June 2011 that Olsen and Timberlake were “hooking up, but trying to keep it on the down-low.”

Scarlett Johansson

The Avengers: Endgame star and Timberlake were linked on more than one occasion after she starred in his 2007 music video for “What Goes Around … Comes Around.” A source revealed to Us in September 2011, “They’ve hooked up several times over the years.”

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