Singer Britney Spears and Justin Timberlake at the 29th Annual American Music Awards in 2002. ; Britney Spears and Sam Asghari at the 29th Annual GLAAD Media Awards in 2019.Photo:Ron Galella, Ltd./Ron Galella Collection via Getty ; J. Merritt/Getty
Ron Galella, Ltd./Ron Galella Collection via Getty ; J. Merritt/Getty
Britney Spearsis 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 withJustin Timberlaketo her"passionate" two-week trystwithColin Farrell.
Spears' first romance in the spotlight was with the former*NSYNCband member, which began in their teens. After their public split, Spears had several boyfriends and got married three times — including toKevin Federline, with whom she shares two sons, andSam 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
Britney Spears and Justin Timberlake at the 2001 American Music Awards.Jeffrey Mayer/WireImage
It was a match made in pop heaven: Spears and Timberlake first met as kids onThe Mickey Mouse Cluband began dating in 1999.
“I was in love with her from the start,” Timberlake saidof 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, andsomeone dared Justin to kiss me,” she wrote. “AJanet Jacksonsong was playing in the background as he leaned in and kissed me.”
The couple becamered carpet fixtures, wearingmatching denimto the 2001 American Music Awards and jerseys with their nicknames to a charity basketball game.
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 choreographerWade Robson, who worked with both the “Toxic” singer and*NSYNCmember, 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.
Dave Hogan/Getty Images
In 2021, Timberlake publicly apologized to Spears after his 2003 interview withDiane Sawyerresurfaced in the documentaryFraming Britney Spears, in which he shared details of their sex life.
“I am deeply sorryfor 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 andJanet Jacksonboth individually, because I care for and respect these women and I know I failed.”
That same year, Timberlake publiclyspoke out in supportof 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.
Colin Farrell
Britney Spears and Colin Farrell at the premiere of ‘The Recruit’ in January 2003 in Hollywood, California.Kevin Winter/Getty
In January 2003, Spears was seen kissing actorColin Farrellat a nightclub in Los Angeles.
Days later, Spears attended the premiere of the Irish star’s filmThe Recruitand 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 flickS.W.A.T.,they had “a two-week brawl.”
“Brawlis 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
KMazur/WireImage ; Enos Solomon/FilmMagic
In January 2004, Spears married Jason Allen Alexander, a childhood friend from her hometown of Kentwood, Louisiana. The couple eloped at theLittle White Wedding Chapelin 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," shewrote 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
Kevin Federline and Britney Spears.Michael Caulfield/WireImage
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 expectinghis second childwith 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.”
Spears also said she wanted tostart a familywithin the next year — and she did just that. She and Federline welcomed their sonSean Prestonon Sept. 14, 2005. Their sonJayden Jameswas 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.”
Kevin Federline and Britney Spears at the 2004 Billboard Music Awards.Kevin Mazur/WireImage
Spears and Federline finalized their divorce in July 2007 with joint physical custody of their two sons. The exes have had severaldifferent custody arrangementssince then.
Despite their ups and downs, Federline said in a 2015 interview that he and Spearsco-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].”
Since then,the singer allowed her kids to movefrom 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
Britney Spears hosts New Year’s Eve 2007 at Pure Night Club in Las Vegas, Nevada. ; Isaac Cohen at Project E “Feed The Models Save The World” to benefit EDIN in 2007.Bruce Gifford/FilmMagic ; Jean Baptiste Lacroix/WireImage
Bruce Gifford/FilmMagic ; Jean Baptiste Lacroix/WireImage
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
Britney Spears attends the Scandinavian Mansion of Style held on December 1, 2007 in Los Angeles. ; Adnan Ghalib poses at the Main Event Red Carpet Lounge and Green Suite on February 21, 2008 in Los Angeles, CA.Jeffrey Mayer/Wireimage ; Michael Bezjian/WireImage
Jeffrey Mayer/Wireimage ; Michael Bezjian/WireImage
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
Jeffrey Mayer/WireImage ; Michael Bezjian/WireImage
Spears briefly dated music producerJ.R. Rotemin 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
Kevin Mazur/WireImage
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.
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
Charley Gallay/Getty
Spears and Virginia nativeDavid Lucadobegan dating in March 2013 after they met at a party. In December of that year, she toldEllen DeGeneresthat 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 splitafter she reportedly discovered a video of him making out with another woman. She addressed the breakup in her Las Vegas residency show, confirming thatLucado had cheated on her.
Charlie Ebersol
Jon Kopaloff/FilmMagic
Spears began dating producerCharlie Ebersol, son of former NBC executive andSaturday Night Liveco-creatorDick 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 Ebersolcalled 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
Britney Spears and Sam Asghari.J. Merritt/Getty
Spears met Asghari on the set of her “Slumber Party"music videoin October 2016 — but she didn’t call him until shefound his phone numberin her bag five months later.
The couplewent Instagram officialin January 2017 and quickly became inseparable. Asghari supported Spears whenher father was illin 2018 and through hermental health treatmentin 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, andwill continue to support herfollowing her dreams and creating the future she wants and deserves,” he told PEOPLE in February 2021.
In September 2021, Spears and Asgharigot engaged. The following June, Spears and Asgharigot marriedin Los Angeles in front of 60 guests, includingMadonna,Paris Hilton,Drew BarrymoreandSelena Gomez.
Britney Spears and Sam Asghari pose for a selfie.Britney Spears Instagram
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 ANDI WISH HER THE BEST ALWAYS.”
A source told PEOPLE that Spears was in “great spirits despite everythinggoing on.”
“Obviously it’s never an easy thing to go through but she’s remaining positive and focusing on the future,” the source added.
source: people.com
