Who Has Justin Timberlake Dated? He Went Out With a Lot of Famous Faces Before Jessica Biel

It's no question that Justin Timberlake is a lucky guy. He's happily married to Jessica Biel — so much so that they're willing to sue anyone who suggests otherwise aww! — and the couple might even have a baby on the way. But before Timberlake wed Biel in 2012, he allegedly dated these women — and some of them are pretty surprising! Check out the list of the women that JT dated before settling down.

by Kaitlin Reilly


Back when she was better known as Stacy Ferguson of Wild Orchird, a 23-year-old Fergie dated 16-year-old Justin Timberlake. (Because I guess the age difference doesn’t matter when you’re an up-and-coming megastar…?) They weren’t meant to be, and Justin Timberlake went on to date…

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Britney Spears

Spears and Timberlake were the biggest pop star couple from 1999 to 2002. That’s when it all went to hell — JT embarked on a solo career, and Spears allegedly cheated on him. Luckily for JT, her cheating sparked one of his biggest singles of said solo career, “Cry Me A River.”

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Jenna Dewan

Dewan (pictured back left!) was a backup dancer and allegedly had a fling with JT during a tour in 2002. It fizzled out, but Dewan went on to have the cutest relationship ever with her now-husband Channing Tatum. Lucky duck.

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Alyssa Milano

Surprising, but the Charmed actress confirmed that she used to date Timberlake right after Brit broke his heart.

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Cameron Diaz

Diaz appeared to be Timberlake’s first serious girlfriend after his relationship with Spears didn’t work out. They dated from 2003 to 2006, and remained good friends after they broke up — they even co-starred in Bad Teacher together as love interests!

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Scarlett Johansson

Rumor has it that Johansson and Timberlake got cozy after starring together in JT’s music video for “What Goes Around…” in 2007. Neither have confirmed a romance, but they were spotted hanging out while Timberlake was on a break from his then-girlfriend Biel.

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Jessica Biel

Biel and Timberlake were spotted out together in 2007, which sparked their five-year-long courtship. It wasn’t always such smooth sailing. The couple broke up briefly in 2011, during which time Timberlake was romantically tied to…

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Ashley Olsen

The designer was linked to Timberlake in 2011 when the pair was spotted getting “flirty” in NYC.

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Olivia Munn

Rumor had it that Munn and Timberlake had a “steamy three-day affair” after meeting doing promotion for Timberlake’s film The Social Network in 2010, which insinuated that he cheated on Biel with Munn. She wasn’t the only Olivia Timberlake would be tied to.

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Olivia Wilde

Wilde and Timberlake — who co-starred in the film In Time together — were spotted getting “cozy” at a club in 2011.

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Jessica Biel (Again!)

After a brief time apart, the pair gave their relationship another shot. Timberlake was all in — he proposed at the end of 2011, and the pair was wed in Italy the following year. Could there be a mini-Timberlake/Biel baby on the way? Well, I guess that depends if you believe all of those rumors… and here’s hoping that they’re true.

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