From Britney Spears to Jessica Biel, Justin Timberlake Has Romanced His Fair Share of A-Listers

Danielle Ditto

Danielle and J.T. dated back when they were teenagers who met in their hometown of Millington, Tennessee. In 2003, Contactmusic reported that she claimed they lost their virginities to each other. “Justin was the perfect guy for it,” she said. “He is sweet, gentle and thoughtful. It was almost like he was trained to be the perfect gentleman.”

Veronica Finn

The Innosense singer also dated Justin before he was out of his teen years. “I was a ‘girl version of Justin.’ We hit it off right away,” she told Star in 2012. “It wasn’t typical dating because we both were touring by then. … But when we had time together, we went to the movies, to the park or just hung out at each other’s house. We even vacationed together in the Bahamas.”

Fergie

Though she insisted on Watch What Happens Live that what she and Justin had “wasn’t all that serious,” the two musicians used to make out back in the day. Though they never formally dated, they did go on vacation together to Hawaii.

Britney Spears

J.T. and Brit’s relationship is bonafide pop culture history — and their 2002 breakup was heartbreaking. Though he never outright accused Britney of cheating at the time, he wrote seriously shady songs — like “Cry Me a River” and “What Goes Around … Comes Around” — that he hinted were about her.

In October 2023, Britney revealed in her memoir, The Woman in Me, that she had become pregnant during her relationship with Justin, although she had an abortion.

“It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated,” she wrote. “But Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.”

Additionally, Britney claimed in her memoir that Justin cheated on her with “another celebrity,” although she did not name the woman because she “has a family [Britney] doesn’t want to embarrass.”

Tonya Mitchell

As it turns out, though, he may have done a bit of cheating himself. Star reported in 2002 that he’d been cheating on Brit with pop singer Tonya Mitchell.

Beyoncé

These two never formally dated, but OK Magazine reported that they did share a smooch back in the day at a party.

Alicia Keyes

J.T. is also rumored to have hooked up with the “Girl on Fire” singer for about a month in 2002.

Jenna Dewan

Before she landed her big break (and ex-husband) in Step Up, she was one of Justin’s backup dancers, and they hit it off. “[It was] not that long. We were friends. Then we dated,” she said on Watch What Happens Live. “We’re still good friends.”

Emma Bunton

In 2018, J.T. admitted that he slept with a Spice Girl, and rumors has it that it was Baby Spice. “We hung out and partied a bit,” she said in a 2004 interview on Friday Night with Jonathan Ross. “He was very sweet.”

Tatyana Ali

In 2003, it was rumored that he was also briefly involved with the Fresh Prince of Bel Air actress.

Cameron Diaz

After Britney, Cameron was J.T. ‘s next serious relationship. After meeting in 2003, they dated for almost four years before announcing their split. “We have … ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another,” they said in a statement at the time. 

However, the end of their relationship seemed pretty shady after rumors swirled that Jessica came in between their relationship. One week after their split, the two ran into each other at Prince’s Golden Globes afterparty and had a heated exchange after Cameron saw the NSYNC alum chatting with the 7th Heaven star. 

After having a 40-minute argument in a private room, eyewitnesses told People that Justin “slammed his fist (down) into a cabinet.”

Alyssa Milano

The Charmed actress was also seeing Justin for a while after his Britney breakup, though their relationship was pretty brief. After his split from Cameron, they hooked up again.

Lindsay Lohan

In 2013, In Touch revealed that J.T. was just one name of many on a handwritten list LiLo had made of celebrities she’d smashed. “It was her personal conquest list,” a source told In Touch. “She was trying to impress her friends with the list and then tossed it aside.”

Jessica Biel

The couple went public in 2007 and were loved up for years. In 2011, however, their romance hit a snag and they briefly broke up in March. By July, they seemed to be back together, and by December, the singer had popped the question. In 2012, they tied the knot and now have two sons.

Rihanna

According to Radar Online, the “Rock Your Body” singer and “Diamonds” songstress went on a couple of dates in 2009 during a rough patch with Jessica.

Olivia Munn

In 2010, Us Weekly reported that he cheated on his then-girlfriend with the Newsroom actress.

Olivia Wilde

The In Time costars allegedly hooked up during those few months when things had cooled off with the musician’s now-wife.

Alisa Wainwright

In November 2019, he was spotted getting handsy with his Palmer costar — though he claimed they only held hands. A source told In Touch in 2019 that the two were “avoiding” each other on set. “They’re staying clear of each other unless they have a scene together,” they revealed. “Justin’s been calling Jessica every hour just to check-in.”