Singer-actor-songwriter Justin Timberlake is a hopeless romantic with his love life grabbing the headlines every once in a while.
The spotlight is once again shining on the enigmatic pop star, as murmurs of his past relationship with Britney Spears resurfaced in the wake of his pointed remarks during a special birthday performance at Irving Plaza in New York City.
Timberlake, before singing his breakup anthem Cry Me a River, unleashed a torrent of words that reignited a flame, which was already simmering after Spears’ revelatory 2023 memoir, The Woman in Me. “I’d like to take this opportunity to apologise to absolutely … nobody,” he said.
In response, the Toxic singer, ever the provocateur, took to Instagram. Wielding her brand of lyrical prowess, she wrote, “Someone told me someone was talking s— about me on the streets.”
As a result, the war of words has made Justin Timberlake’s dating history ever more intriguing. Apart from sharing a much controversial romantic past with Spears, this Hollywood heartthrob has been entangled with a bunch of other popular names.
From fleeting romances with Tonya Mitchell and Alicia Keys to fonder bonds forged with ex-girlfriend Cameron Diaz and wife Jessica Biel, Timberlake’s romantic journey is as envious as it is complicated.
But just so you don’t have to invest much in figuring out ‘who all has Justin Timberlake dated’, we have done the research for you and are ready to unravel…
Justin Timberlake’s complete dating history and list of girlfriends
Here’s how this pop sensation and charmer extraordinaire traversed the landscape of love with a swagger, leaving a trail of broken hearts and whispered rumours in his wake.
Fergie (1996): A ’90s fling
Fergie was one of the first few famous names romantically linked to Justin Timberlake. The Black Eyed Peas alum and the Friends with Benefits actor had a fling back in 1996, courtesy of NSYNC’s lead vocalist and Justin’s friend J.C Chasez dating one of Fergie’s friends. So, they all would hang out together.
Much later, the two also collaborated on the song Where is the Love? and Fergie dished on the juicy details a few years later in an interview with Cosmopolitan. “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. We went to Hawaii together, but we were never serious,” she shared setting the record straight about the nature of their relationship.
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Veronica Finn (1997): Another teenage romance
Justin and ex Veronica Finn, 1998. pic.twitter.com/WN70TxeyMQ
— JT ARCHIVES (@JT_ARCHIVES) January 19, 2022
Justin and Victoria were in their late teens when they started seeing each other in 1997, at the height of Justin’s NSYNC career. The two would spend their off-tour time together and enjoyed going to the movies, visiting parks and simply hanging out at each other’s homes. They even took a vacation in the Bahamas.
However, after a year together, Veronica suspected Justin of infidelity which led her to end the sweet teenage love saga.
Britney Spears (1999-2002): A Hollywood era
Britney Spears reveals in her memoir that Justin Timberlake cheated on her with another celebrity during their releationship, TMZ reports. pic.twitter.com/oPeU0KO3XJ
— Pop Base (@PopBase) October 18, 2023
The most famous and controversial name to go down in Justin Timberlake’s dating history is that of pop princess Britney Spears. The two started dating in the late ’90s when they were at the top of their music careers.
The pop icons, first stole hearts as co-stars in The Mickey Mouse Club, navigating the complexities of fame and young love during the late 1990s and early 2000s. In her recent memoir, Spears candidly shares intimate details of her life, including her high-profile relationship with Timberlake.
One of the memoir’s most shocking revelations revolves around an unexpected turn in their relationship – Spears’ unplanned pregnancy. Spears discloses the emotional turmoil she experienced despite her desire to embrace parenthood as Timberlake was not ready to become a father. She expresses her internal conflict, revealing that if the choice had been solely hers, she might have chosen to have the child.
As per Timberlake, however, the two split because Spears had cheated on him. He also reportedly ended the relationship through a brief text message. But later the former NSYNC member also released a song – Cry Me a River – about it, with the music video featuring a Britney lookalike, proving that he was as affected by the breakup as Spears.
Tonya Mitchell (2002): A rebound
In the aftermath of his much-discussed breakup with Britney, Justin went around getting involved in a couple of casual relationships. Pop singer Tonya Mitchell happens to be one of those rebounds. In fact, Star reported in 2002 that Justin was accused of cheating on Britney during the end of their relationship with Tonya.
Alicia Keys (2002): Another rebound
The Mirrors singer has also been rumoured to have hooked up with the Girl on Fire singer Alicia Keys for about a month in 2002 while he was on a rebound spree.
Jenna Dewan (2002): The interlude
After Alicia, Justin sought solace in the company of Jenna Dewan. A backup dancer at the time, Dewan confirmed their relationship during an appearance on Watch What Happens Live, emphasising the friendship that characterised this post-Britney interlude.
While their connection was not long-lasting, it marked a transitional phase in Timberlake’s romantic journey.
Alyssa Milano (2002): The ‘Charmed’ star
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Justin Timberlake’s dating timeline and list of girlfriends just skyrocketed in the year 2002 with a new girl entering his life every other month. After Jenna, he entered into a relationship with Alyssa Milano, known for her role in the Social Network and Charmed.
However, Milano’s revelation during a 2015 interview added a twist to the narrative. Despite being romantically involved with Timberlake at the time, Milano confessed to rooting for his previous flame, Britney Spears, citing their undeniable compatibility.
Cameron Diaz (2003-2006): A steady relationship
After a good run of flings, Justin got into a serious relationship with Cameron Diaz. Their connection, spanning from 2003 to 2006, showcased both on and offscreen chemistry. The former flames later reunited for the film Bad Teacher in 2011.
Diaz, speaking about their three-year-long relationship, emphasised the laughter and camaraderie they shared, acknowledging their amicable parting.
Beyoncé (2006): Just a lip lock or more?
While Queen Bey never officially made it to the list of Justin Timberlake’s girlfriends, the two collaborated on their 2006 song Until the End of Time and reportedly locked lips later.
OK Magazine reported that Beyoncé and Timberlake did share a smooch back in the day at a party.
Jessica Biel: (2007-Present) The wife
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After Cameron, Justin Timberlake’s dating history took another serious turn when he started seeing actress Jessica Biel. The two made their relationship public in January 2007. However, their love life has faced many challenges since then. In 2011, they briefly split, but soon reconciled and got engaged in January 2012. Later in October of the same year, they got married. After enjoying marital bliss for three years, Timberlake and Biel embraced parenthood in April 2015 and welcomed their son, Silas.
However, rumours about their marriage’s stability persist. Reports mention unsuccessful couples therapy and recent real estate moves hinting at financial changes.
Their history includes more than a few reconciliations after separations. Yet, insiders now suggest a potential permanent split, especially with Britney Spears’ revelations in her book affecting Biel’s trust.
While they tried to show unity at a Trolls Band Together screening, doubts linger about their relationship’s authenticity. With two children, Silas and Phinneas, they face a crucial moment. Despite rumours of Biel considering divorce, her recent support for Timberlake after the release of Spear’s memoir and a loved-up post on Justin’s 43rd birthday hint at their ongoing commitment.
Rihanna (2009): A few casual dates
Reportedly, Timberlake and pop sensation Rihanna went on a few dates in 2009 when the former was going through a rough time with his now-wife Jessica but nothing fonder grew from those few dates.
Olivia Munn (2010): A ‘ONS’
Justin reportedly cheated on Jessica with the former TV host and actor Olivia Munn in 2010.
Alisha Wainwright (2019): The girl who caused a stir
Justin Timberlake’s Palmer co-star, Alisha Wainwright, caused a stir in November 2019 when they were seen holding hands. Following a month of cheating rumours, the Stay With Me singer finally addressed the incident.
“I drank way too much that night, and I regret my behaviour. I should have known better. This is not the example I want to set for my son,” he stated in a December 2019 statement, adding, “I apologise 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.”
Well, as Justin Timberlake navigates the chords of love in life, one thing remains certain: the journey is far from over, and the music plays on.
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(Header and feature image courtesy: Instagram/Jenna Dewan/Alisha Wainwright/Jessica Biel/Justin Timberlake)
Frequently Asked Questions (FAQs)
– Who are Justin Timberlake’s ex-girlfriends?
Justin Timberlake’s ex-girlfriends include Britney Spears, Fergie, Veronica Finn and Cameron Diaz, among others.
– Who did Justin Timberlake date at 16?
At 16, Justin Timberlake dated Veronica Finn, a fellow singer.
– Who is Justin Timberlake married to?
Justin Timberlake has been married to Jessica Biel since October 2012.
– Why did Jessica and Justin break up?
Jessica Biel and Justin Timberlake briefly split in 2011 due to undisclosed reasons, but they reconciled and got engaged later that year.
