Justin Timberlake Has a Lengthy Dating History! Meet His Ex-Girlfriends and Flings Over the Years

Danielle Ditto

Justin and his teenage love dated during their adolescent years in their hometown of Millington, Tennessee. Years after their romance, Danielle claimed Justin was “perfect” when they allegedly lost their virginities to one another.

“He is sweet, gentle and thoughtful. It was almost like he was trained to be the perfect gentleman,” she told Contactmusic in 2003.

Veronica Finn

Justin and Victoria spent their free time together when neither of them were on the road touring and started dating in 1997, during the peak of his ‘NSync career.

“When we had time together, we went to the movies, to the park or just hung out at each other’s house,” she told Star in 2012. “We even vacationed together in the Bahamas.”

After one year together, Veronica ended things with Justin after she suspected he wasn’t being faithful to her.

Fergie

Fergalicious definition makes Justin go loco! The Black Eyed Peas alum and Trolls actor got together after their 2003 collaboration on the hit “Where Is the Love?” and Fergie dished on the juicy details three years later.

“One of my good friends was dating J.C. Chasez, and so we’d all hang out with ‘NSync. Justin and I would go out together and have fun and make out,” she told Cosmopolitan. “We went to Hawaii together, but we were never serious. He was Mr. Right Now.”

Britney Spears

You can’t not think of these two when you hear “Y2K.” Justin and Britney started dating in 1999 during the height of their music careers and instantly became the It Hollywood couple.

They may have looked like a picture-perfect pair, but the Grammy winners called it quits in 2002 after three years of dating. Years after their breakup, dark secrets started to arise from their romance.

Britney released her memoir The Woman in Me in October 2023, where she revealed she had an abortion after getting pregnant during her relationship with Justin.

“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.”

Tonya Mitchell

Justin was accused of cheating on Britney during the end of their relationship with Tonya after Star reported their alleged romance in 2002.

Beyoncé

Justin and Queen Bey collaborated on their 2006 song “Until the End of Time” and reportedly locked lips once.

Alicia Keys

The “Rock Your Body” singer was reportedly romantically linked to Alicia for a month in 2002 but never officially dated.

Jenna Dewan

Justin couldn’t stop the feelings he had for Jenna when she was his backup dancer before her Blockbuster debut.

“[It was] not that long. We were friends. Then we dated,” the Step Up actress previously said on Watch What Happens Live. “We’re still good friends.”

Emma Bunton

Justin really, really, wanted to hook up with a Spice Girl – so he did! In 2018, the Reptile actor revealed that he hooked up with one of the beauties from the girl group, but didn’t disclose who.

However, fans believe he was getting his SexyBack with Baby Spice after she claimed to “hang out” and party “a bit” with Justin in 2004.

Tatyana Ali

Rumors swirled that he took a trip to Bel Air and casually dated Tatyana in 2003.

Cameron Diaz

Justin decided to stop being lowkey with his love life and took his romance with Cameron public in 2003.

They split four years later after word was spreading that his now-wife Jessica turned his head from The Mask actress.

Alyssa Milano

The Charmed actress seemingly lifted Justin up while he was getting over his breakups with Britney and Cameron as she reportedly hooked up with him at the end of both relationships.

Lindsay Lohan

Justin’s name appeared on a handwritten list the Mean Girls star made of the men she had slept with in 2013.

Jessica Biel

Justin and Jessica have experienced a rocky relationship, though they have managed to keep a brave face to the public. The pair started dating in 2007 and decided to put a pause on their relationship in March 2011. They rekindled their love four months later and got engaged shortly after.

After tying the knot in 2012, they have since welcomed sons Silas and Phineas.

Rihanna

Justin and RiRi went on a few dates in 2009 during a hard time with Jessica, Radar previously reported.

Olivia Munn

Us Weekly reported that Justin cheated on Jessica with the former TV host in 2010.

Olivia Wilde

The Don’t Worry Darling director was sexually intimate with the “Suit and Tie” musician during his brief breakup with Jessica in 2011.

Alisha Wainwright

Justin was in hot water after he was spotted holding hands with his Palmer costar in November 2019.

After cheating rumors surrounded him for one month, the “Bye Bye Bye” singer broke his silence on the incident.

“I drank way too much that night and I regret my behavior. I should have known better. This is not the example I want to set for my son,” he said in a December 2019 statement. “I apologize to my amazing wife and family for putting them through such an embarrassing situation, and I am focused on being the best husband and father I can be.”