Britney Spears’ Dating History: From Her High-Profile Romances to Her Three Marriages

Britney Spears famously dated Justin Timberlake before going on to marry Kevin Federline in 2004 and Sam Asghari in 2022

Britney Spears is getting candid about her past relationships.

In her new memoir, The Woman in Me, the "Lucky" singer opens up about her high-profile dating history, revisiting everything from her infamous breakup with Justin Timberlake to her "passionate" two-week tryst with Colin Farrell.

Spears' first romance in the spotlight was with the former *NSYNC band member, which began in their teens. After their public split, Spears had several boyfriends and got married three times — including to Kevin Federline, with whom she shares two sons, and Sam Asghari, who filed for divorce in August 2023 after one year of marriage.

Despite the ups and downs in her dating life, the Grammy winner has never stopped believing in happy endings. Prior to meeting Asghari, Spears told PEOPLE in 2015 that she hadn't given up on love.

"I believe in the fairy tale. Love is a hard one. I don’t really understand love as far as relationships. With my kids it’s just unconditional, and that’s hard to find. It takes two people just loving each other a lot," she said.

Here's a look back at Britney Spears' dating history.

Justin Timberlake

It was a match made in pop heaven: Spears and Timberlake first met as kids on The Mickey Mouse Club and began dating in 1999.

"I was in love with her from the start," Timberlake said of Spears in 2006. "I was infatuated with her from the moment I saw her."

In her memoir, Spears shared her own early recollections of their romance. “[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me,” she wrote. “A Janet Jackson song was playing in the background as he leaned in and kissed me.”

The couple became red carpet fixtures, wearing matching denim to the 2001 American Music Awards and jerseys with their nicknames to a charity basketball game.

Related: Britney Spears and Justin Timberlake's Relationship: A Look Back

In March 2002, however, the reigning prince and princess of pop shocked the world with news of their split. Rumors quickly spread that Spears had cheated with choreographer Wade Robson, who worked with both the "Toxic" singer and *NSYNC member, though neither Spears nor Robson addressed the chatter at the time. (Spears confirmed that they had kissed while she was dating Timberlake in her memoir).

After the breakup, Timberlake released his "Cry Me a River" music video, which famously featured an unfaithful girlfriend that looked an awful lot like his ex.

In The Woman in Me, Spears reflected on the media backlash caused by the video, which she says painted her as a "harlot who'd broken the heart of America's golden boy," when in actuality, she was "comatose in Louisiana, and he was happily running around Hollywood."

In 2021, Timberlake publicly apologized to Spears after his 2003 interview with Diane Sawyer resurfaced in the documentary Framing Britney Spears, in which he shared details of their sex life.

"I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn or did not speak up for what was right," Timberlake wrote on Instagram. "I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed."

That same year, Timberlake publicly spoke out in support of ending Spears' conservatorship. And though Spears briefly addressed their history in the past — she once wrote on Instagram that despite having "one of the world’s biggest breakups," she considers Timberlake a genius — she didn't fully open up about their breakup until the release of her memoir.

In her book, Spears reexamines some of the most difficult moments of her life, including when she became pregnant with Timberlake's baby and had an abortion. Although the pregnancy was a "surprise" for Spears, "it wasn’t a tragedy," as she always expected them to have a family one day. However, she and Timberlake weren't on the same page.

“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," she wrote.

Colin Farrell

In January 2003, Spears was seen kissing actor Colin Farrell at a nightclub in Los Angeles.

Days later, Spears attended the premiere of the Irish star's film The Recruit and left early — but that night, she and Farrell were seen kissing on a balcony at the Chateau Marmont in Hollywood.

"She's just a mate," he told reporters at the premiere. "Seriously, we just met a week ago, [we're] having a laugh." Spears' publicist added, "They're friends."

However, Spears later got more candid about her fling with Farrell in her memoir. The “Piece of Me” singer wrote that after meeting the actor while he was filming the 2003 action flick S.W.A.T., they had "a two-week brawl."

"Brawl is the only word for it — we were all over each other, grappling so passionately it was like we were in a street fight," she wrote.

Despite their connection, Spears added that she tried to avoid getting “too attached” to Farrell when she was still hung up on Timberlake. “As I had before when I’d felt too attached to a man, I tried to convince myself in every way that it was not a big deal, that we were just having fun, that in this case I was vulnerable because I wasn’t over Justin yet,” she wrote.

Jason Alexander

In January 2004, Spears married Jason Allen Alexander, a childhood friend from her hometown of Kentwood, Louisiana. The couple eloped at the Little White Wedding Chapel in Las Vegas; Spears wore jeans and a baseball cap as a hotel employee escorted her down the aisle.

Spears and Alexander obtained their marriage license at a Las Vegas courthouse before the ceremony. A source told PEOPLE that the wedding was "a joke that went too far."

Just 55 hours after tying the knot, Spears filed to annul her marriage to Alexander.

“People have asked me if I loved him. To be clear: he and I were not in love," she wrote in her memoir. "I was just honestly very drunk — and probably, in a more general sense at that time in my life, very bored."

Spears also reveals in the book that her parents, Jamie and Lynne, were upset about the impromptu nuptials.

"They made way too big a deal out of innocent fun," she wrote. "Everybody has a different perspective on it, but I didn't take it that seriously. I thought a goof-around Vegas wedding was something people might do as a joke. Then my family came and acted like I'd started World War III. I cried the whole rest of the time I was in Las Vegas."

Kevin Federline

Spears met Federline, a former backup dancer for Timberlake, at a club in 2004, and it was love at first sight.

"Our eyes met and that was it. We just hit it off right away. I was madly in love with her," he told PEOPLE in 2008. "Everything just seemed so right. I didn't see it as too fast or too slow." At the time, Federline was expecting his second child with his ex, Shar Jackson.

Spears and Federline scrapped their plans for a lavish ceremony and wed on Sept. 18, 2004, after three months together.

"I just thought it would be too much if we had done it when we were supposed to," Spears told PEOPLE of their surprise wedding, originally planned for October 16. "It became this huge thing and I was like, 'What are we waiting for? We know this is the real thing, why not just do it now?' That's why I wanted to sneak and do it our little way."

Related: Britney Spears and Kevin Federline's Relationship Timeline

Spears also said she wanted to start a family within the next year — and she did just that. She and Federline welcomed their son Sean Preston on Sept. 14, 2005. Their son Jayden James was born on Sept. 12, 2006.

In November 2006, eight weeks after Jayden was born, Spears filed for divorce from Federline, citing "irreconcilable differences."

Two years later, Federline told PEOPLE that the couple had problems, but he wasn't expecting the breakup.

"We were having complications ... but I was trying to work stuff out with her," he said. "I did everything that I could to cater around the whole situation: built a recording studio in the house, made sure I could always work at home, try to help out as much as I can. ... I don't know, I guess it wasn't enough."

Spears and Federline finalized their divorce in July 2007 with joint physical custody of their two sons. The exes have had several different custody arrangements since then.

Despite their ups and downs, Federline said in a 2015 interview that he and Spears co-parented amicably. "The family is great," he said. "It's been a long, long journey, but I think where both of us are now, we both have somebody else we're happy [with]."

In August 2022, Federline shared his thoughts on the conservatorship that Britney was put under by her father, Jamie Spears, saying that the arrangement "saved" her. However, he admitted that the situation had been hard on their sons, whom he claimed were choosing not to see their mother. Spears addressed his comments on Instagram, writing, "Only one word: HURTFUL."

Since then, the singer allowed her kids to move from California to Hawaii with Federline in May 2023. The former dancer cited work opportunities for him and his wife of 10 years, Victoria Prince, as the reason.

Isaac Cohen

In January 2007, Spears was linked to model Isaac Cohen after they stayed at a hotel in Las Vegas, were spotted together in L.A. and went out on powerboats in Marina Del Rey, California.

"[Isaac] is not a player," Cohen's agent Brandi Lord told PEOPLE. "He's got a great heart and a good family, and he was raised well. He's a gentleman."

By February 2007, the fledgling couple had called it quits. Lord told PEOPLE about the "very amicable" split: "They're both busy with their careers. They were never getting married. They were having fun together."

Adnan Ghalib

Paparazzo Adnan Ghalib claimed he and Spears began dating in December 2007 — while he was married. Ghalib's photo agency, FinalPixx, published several exclusive photo sets of the photographer with Spears, including their vacation to Mexico.

The next month, the same day his wife filed for separation, Ghalib told the press that he and Spears were in love and that their relationship was “far from over.”

Just over a year later, in March 2009, Jamie Spears obtained a restraining order against Ghalib. Ghalib was prohibited from seeing or contacting the singer for three years.

J.R. Rotem

Spears briefly dated music producer J.R. Rotem in late 2007.

After their fling ended, Spears and Rotem worked together, and the producer had nothing but compliments for the pop superstar.

"She's great," he told PEOPLE. "She's like a master at what she does. She's a lot more experienced than most people. She just has the 'it' factor that not every artist has. So it's always nice to work with her."

Jason Trawick

In 2009, Spears began dating her then-agent, Jason Trawick. "They are totally and definitely dating," a source told PEOPLE at the time.

Trawick later recalled that Spears made the first move. "It was kind of one of those things where she moved, like, turned around, so we were face to face," he said.

After two years together, Trawick resigned as Spears' agent, a move spurred by his romance with the singer. "Since meeting Britney, his priorities have shifted," a source told PEOPLE. "He would much rather be home at night with her and her boys."

Following Trawick's appearance in Spears' "Criminal" music video, he popped the question while celebrating their birthdays together in December 2011. At Spears' request, her then-fiancé was named a co-conservator alongside her father.

By January 2013, the couple called their engagement off. "Britney Spears and Jason Trawick have mutually agreed to end their one-year engagement," Spears' rep told PEOPLE. "As two mature adults, they came to the difficult decision to go their separate ways while continuing to remain friends."

In a statement, Spears said, "I'll always adore him and we will remain great friends." Trawick added, "As this chapter ends for us a new one begins. I love and cherish her and her boys and we will be close forever."

David Lucado

Spears and Virginia native David Lucado began dating in March 2013 after they met at a party. In December of that year, she told Ellen DeGeneres that her friends introduced her to him, and there was a mutual attraction.

"I think it was instant," she said. "He's very passionate and he's funny and he's sexy."

After dating for several months, Spears said she was "in love." The following month, Spears added, "I like the fact that he's very stubborn and he's stuck in his ways."

In August 2014, Spears and Lucado split after she reportedly discovered a video of him making out with another woman. She addressed the breakup in her Las Vegas residency show, confirming that Lucado had cheated on her.

Charlie Ebersol

Spears began dating producer Charlie Ebersol, son of former NBC executive and Saturday Night Live co-creator Dick Ebersol, in October 2014. "It's new," a source told PEOPLE at the time. "[They're] taking it slow."

The singer met Ebersol through her assistant. "I thought he was really adorable and she said he was good to people, so I went for it," she told PEOPLE.

Per her request, Ebersol cooked Spears dinner for their first date, and she was hooked. "There was something about him that made me feel really peaceful and at ease," she added. "And he was really hot, too. Adorably hot."

In June 2015, Spears and Ebersol called it quits. The couple's spark had faded, and Ebersol was particularly heartbroken — one source said they thought he would propose.

"Charlie has been pretty torn up about all of this," another source added. "He really thought she could be the one. He is a very private, family guy and saw Britney fitting right in."

Sam Asghari

Spears met Asghari on the set of her "Slumber Party" music video in October 2016 — but she didn't call him until she found his phone number in her bag five months later.

The couple went Instagram official in January 2017 and quickly became inseparable. Asghari supported Spears when her father was ill in 2018 and through her mental health treatment in 2019.

Ahead of her conservatorship court hearing, Asghari sported a "Free Britney" T-shirt, and he was there for her throughout the trial. "I have always wanted nothing but the best for my better half, and will continue to support her following her dreams and creating the future she wants and deserves," he told PEOPLE in February 2021.

In September 2021, Spears and Asghari got engaged. The following June, Spears and Asghari got married in Los Angeles in front of 60 guests, including Madonna, Paris Hilton, Drew Barrymore and Selena Gomez.

One year later, Asghari filed for divorce, listing their date of separation as July 28. The next day, the personal trainer addressed the matter on his Instagram Story.

"AFTER 6 YEARS OF LOVE AND COMMITMENT TO EACH OTHER MY WIFE AND I HAVE DECIDED TO END OUR JOURNEY TOGETHER," he wrote. "WE WILL HOLD ONTO THE LOVE AND RESPECT WE HAVE FOR EACH OTHER AND I WISH HER THE BEST ALWAYS."

A source told PEOPLE that Spears was in "great spirits despite everything going on."

“Obviously it's never an easy thing to go through but she’s remaining positive and focusing on the future," the source added.

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