Inside Britney Spears' Relationship With Kevin Federline Over The Years

Britney Spears isn't shy to speak about her past relationships, even when things were less than lovely. In a 2016 interview with Australia's talk radio show "Rove & Sam," she joked, "Unfortunately, I am [a hopeless romantic]." She went on, "I've been through horrible relationships, but unfortunately I still believe in love. And you know, I think you should protect your heart and stuff like that. But yeah, I'm a hopeless romantic and I believe in love."

Our girl has had a series of highly publicized relationships since her ascent to fame and some, as she said herself, weren't so great. Spears dated Justin Timberlake from 1998 to 2002, per The Sun. Their very public breakup was marred by rumors of infidelity on Spears' part, something that Timberlake seemed to imply, especially in his 2002 song, "Cry Me a River." Years later though, after the release of the 2021 documentary by The New York Times, "Framing Britney Spears," Timberlake came forward to apologize. "I am deeply sorry for the times in my life where my actions contributed to the problem," he wrote on Instagram, (via The Sun). Timberlake pointedly apologized to Spears and Janet Jackson. "I care for and respect these women and I know I failed," he went on.

After that very public debacle, Spears married Jason Alexander for 55 hours and the marriage was annulled shortly after, per Us Weekly. Spears had a few other flings but it was her relationship with Kevin Federline that changed her life.

Britney Spears and Kevin Federline met in 2004 while out partying one night, only weeks after Spears' 55 hour marriage to Jason Alexander. "I met her at a club in Hollywood, Joseph's," Federline told People in 2008. "Our eyes met and that was it. We just hit it off right away." When he met Spears, Federline was already a father to daughter Kori, whom he shared with Shar Jackson, and Jackson was expecting their second child, according to E! News. Ironically enough, Federline had previously been a backup dancer for Spears' ex, Justin Timberlake.

The massive publicity of their romance proved to be a challenge at times, but Federline reminisced to People that they managed to carve out some alone time. "We felt like — or at least I felt like — we had a little bit of a private life," he said. "It's not like they knew everything that we would say to each other or every great moment that we would have. I was madly in love with her. Everything just seemed so right. I didn't see it as too fast or too slow."

When Spears injured her knee, enough that she had to get surgery, cancel tours, and take four months to recuperate, she ended up proposing to Federline. He flipped it by proposing to her moments later and they were officially a pop star duo for the ages. "I don't look at her as 'Britney Spears,' he said. "I look at her as somebody that I fell in love with."

The inevitable then happened in Britney Spears and Kevin Federline's relationship: they made a reality show. "Britney & Kevin: Chaotic" aired in 2005 and never made it past the first five episodes because reviews were abysmal. The footage was shot on a camcorder, held by either Spears or Federline and featured sometimes overly sexualized footage, Variety notes, making it unsuitable for younger audiences and too silly for older viewers.

The show was aired on United Paramount Network and the filming quality was raw and the sound quality was poor enough that many scenes required subtitles. But "Britney & Kevin" did serve one vital purpose for the couple, especially for Spears, who was tabloid fodder at this point to an almost uncontrollable level. Speaking of the inaccurate coverage on their relationship, Spears said in a statement about the show: "I feel that last year, the tabloids ran my life, and I am really excited about showing my fans what really happened, rather than all the stories, which have been misconstrued by journalists in the past," per MTV. 

It was a chance for Spears to control her own narrative and give viewers a chance to see their relationship literally through their gaze. "I am now going to be expressing my personal life through art," she said. The series wrapped with Spears and Federline getting married, so it really spanned their relationship from its inception to the altar.

Britney Spears and Kevin Federline didn't waste any time tying the knot. Approximately three months after they started dating, the duo surprised their family and friends with a small ceremony at a home in Studio City, per E! News. On September 18, 2004, Spears and Federline gathered 27 guests for what they thought would be an engagement party and turned out to be their actual wedding. Spears had pink Juicy Couture tracksuits waiting for her bridesmaids, with "The Maids" fittingly embroidered. The groomsmen got white tracksuits with "Pimps" written on them. Spears wore a white wedding dress by Monique Lhuillier and People bought the rights to their wedding photos for $1 million.

Family and friends were expecting their wedding to take place one month later at the Bacara Resort in Santa Barbara, California, which is what the couple had originally planned for. But the growing hype around the big day, including a frenzy of media attention, inspired the couple to opt for a surprise. "I just thought it would be too much if we had done it when we were supposed to," Spears explained to People. "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." For their honeymoon, the couple stayed local and got a suite at the Hotel Bel-Air and told People that they felt "awesome."

Britney Spears confessed that she wanted to be a mom from the get-go. Right after her wedding to Kevin Federline, when she was only 22, the pop icon said that she wanted to be a young mom. "A lot of people think you should wait till you're older to have kids," Spears admitted on her website at the time, per Us Weekly. "I've had a career since I was 16, have traveled around the world and back, and even kissed Madonna!" She added, "The only thing I haven't done is experience the closest thing to God, and that's having a baby. I can't wait!"

Sure enough, when Spears was 23, she and Federline welcomed their son Sean Preston in 2005, according to People, and in 2006, they had their second son, Jayden James. To spend time together as a family, Spears slowed her work schedule and the pace was surprisingly delightful to her. "I thought I would never say this, but I love not working so much!" she admitted on her website. "To be a really good mom, I feel your child needs to be your full-time job. I want to raise my kids and share all of those precious moments with them, and not rely on nannies." 

Clearly, taking a step back from her career to enjoy family time was something Spears didn't even know she needed until she got the chance to do so and being a hands-on mom was right up her alley. 

While it looked like Britney Spears and Kevin Federline got everything they wanted, at least from an outside perspective, they called it quits in 2006, only two months after the birth of their second child. Apparently, things were rocky following the arrival of their boys and things got pushed to a breaking point. An insider told People that only three weeks after they welcomed Jayden James, Federline took off to party in Las Vegas with friends. Spears felt overwhelmed and abandoned with two young sons in tow.

Shortly after, when Federline was in Toronto to promote his new album, Spears, who was in New York City, filed for divorce, claiming irreconcilable differences. She was then spotted having dinner with friends followed by ice skating at Rockefeller Center. Sources at the time reported that Spears looked elated while Federline looked crushed and sad.

In 2016, Federline spoke with "VLAD TV" and his relationship with Spears came up, reluctantly. He first admitted that he was done talking about that period in his life but then opened up. "That was a whole different lifestyle than I ever imagined," Federline said. "I mean, just getting around from place to place and having 20 people follow you all day long ... your whole life kind of being told through somebody else's eyes. Everybody wants to put their own spin on it." Their status as celebrities took a huge toll on their relationship. Federline added, "It was so crazy. I look back at it and it's like, at times it was so overwhelming."

Unsurprisingly, Britney Spears and Kevin Federline did not get married without an air-tight prenup, which was the right thing to do since money was certainly part of the equation when their divorce finalized in 2007. While Federline obviously loved Spears, the glamorous lifestyle she offered was something he brought up. "I soaked up as much of the lifestyle as I could," he told Us Weekly at the time (via Independent). "I'd walk into a club and get a table worth $15,000 a night with unlimited free drinking." Federline went on about the financial impact of his relationship with Spears, "To not have to worry about making my next car payment felt like a huge weight lifted off my soul. But everything got so crazy."

So when it came to the divorce settlement, Spears enlisted the help of celebrity attorney Laura Wasser, according to E! News. Federline walked away with $1 million and also received $20,000 a month for child support. The topic of Federline's monthly payments has been an ongoing issue between the couple. Even in 2018, TMZ reported that there was an ongoing discussion between his and her lawyers. Allegedly, Federline asked for $60,000 a month, which Spears' team refused on the grounds that she pays for her sons' school tuition and all their other expenses, so Federline's request didn't seem warranted. Apparently Spears' father, Jamie Spears, who was her guardian at the time under their conservatorship, was especially reluctant because he felt that Federline was taking advantage of Britney's finances.

On February 17, 2007, Britney Spears drove to a hair salon in Los Angeles and asked the stylist, Esther Tognozz, to cut her hair, after checking out of rehab earlier. When Tognozz refused, Spears buzzed her hair off herself. The highly-publicized event, thanks to the torrent of paparazzi following Spears everywhere, sparked what the media called her downfall and got the wheels turning for her conservatorship. But earlier on that fateful night, Spears had driven to Kevin Federline's home because she wanted to see their sons. When Federline refused, Spears drove away and stopped at the hair salon.

Later on that same night, after Spears left the salon, she walked into Body and Soul Tattoo parlor and artist Emily Wynne-Hughes later recalled the conversation she had with Spears that night. Wynne-Hughes said that she asked Spears why she had cut her hair, and later reported Spears' response. "It was, you know, 'I just don't want anybody, anybody touching my head. I don't want anyone touching my hair. I'm sick of people touching my hair,'" the tattoo artist recalled, according to the Mirror.

Spears was clearly facing a challenging situation, having just gone through a divorce and seeing less of her sons thanks to the custody arrangements. Being hounded by the press only exacerbated the building stresses and Spears was starting to gain negative traction in the media. Allegedly, as E! News reports, her behavior made Federline reluctant to sign the divorce papers because he wanted to see how things would sort out.

After Britney Spears was photographed shaving her head, growing concern led to a shift in custody arrangements with Kevin Federline over their two sons, Sean Preston and Jayden James. Following this 2007 incident, a judge awarded full custody to Federline, The Sun reported. Spears had enrolled in a rehab program but checked out 24 hours later and as such, was required to submit to random drug and alcohol testing, The Orange County Register reported in 2007. However, in October of that year, Spears allegedly missed one of the substance abuse tests, which was a score against her. 

Things took a serious turn again in 2008 when she refused to give Jayden James back to Federline's bodyguards, who had arrived at her home to collect the children after their visit with Spears and return them to their father, according to The Guardian. Spears locked herself in her bathroom with her youngest son, which led to a four hour impasse with police. Once she relinquished her son, Spears was taken out of her home on a stretcher and taken to Cedars-Sinai Medical Center where she was cared for and held on a 5150, on the grounds that she could potentially hurt herself or others. In light of all of this, Spears lost custody of her sons. This also meant that her father stepped in and the wheels of the conservatorship started rolling.

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With her divorce from Kevin Federline and losing custody of her two children, Britney Spears was facing relentless scrutiny from the media. In response, Jamie Spears filed for conservatorship of his daughter, per the BBC, which was initially temporary and became permanent later in 2008.

Jamie's lawyer said that the extreme measures were "necessary to protect Britney in every sense of the word." His legal team added, "Her life was in shambles and she was in physical, emotional, mental and financial distress." Such action is typically taken for an individual who is incapable of making sound personal decisions and in Britney's case, her father requested two separate components: her financial assets and her as a person. As Spears later said in court, the conservatorship controlled all aspects of her life. She wasn't allowed to have her birth control removed, even after expressing the desire to have another child.

So what did Federline think of all of this? "It was extremely tough watching her go through a phase where she was clearly not okay right after the divorce," he said, according to the Independent. "There's a lot more I could have done to help. Taking full custody of the boys sucked the life out of me, but it was for them, he added. "I have to give Britney's dad, Jamie, a lot of credit for saving her. He made it so I could actually deal with her again." Clearly, Federline took both sides in the story. 

While Kevin Federline will always be linked to Britney Spears thanks to their children, the dancer found love again with Victoria Prince, who was as non-famous as someone in Federline's shoes could hope for. He met Prince at a bowling league, according to People. Prince was a varsity volleyball player from Kennewick, Washington. Prince and Federline began dating in 2008 and he had her meet Spears early on and he even brought Prince to Miami for Spears' "Circus" tour, where they hung out at the Mandarin Hotel with the pop star and her family.

Federline and Prince got married in 2013 and welcomed two children, Jordan and Peyton, and while Federline admits that there were stressors in his relationship with Spears, he also admitted to Us Weekly that he learned a lot from her and that relationship. "Things that [Britney] brought out in me were, a better sense on having a great relationship with somebody," he said. "I really learned a lot about what I like in a person from her, a lot."

So what's his current relationship life? "Vic is my best friend," Federline said of his wife. "We work well together. We both want the same things for our children. Me and Vic know how to have fun together and I think that's important." So between the children he has with Shar Jackson, Spears, and Prince, Federline is a father to six kids.

Britney Spears' conservatorship ended in November 2021, taking the role of guardianship away from her father, Jamie Spears. His presence in her life seriously affected Britney's ability to connect with her sons because in 2019, Jamie and her oldest son, Sean, had an altercation where Jamie "violently shook" him, according to The Blast. In response, Jamie was hit with a restraining order and not permitted to see his two grandsons. So, with less of Jamie around, Britney has more freedom to interact with her boys.

Federline had positive things to say about the end of her conservatorship and was very happy for his ex. His attorney, Mark Vincent Kaplan, told People what Federline's views were. "If Britney wants to see the children, she's able to see the children," Kaplan explained. "Obviously we don't know whether the conservatorship will be continued, but as long as the boys are properly supervised and safe, and Britney is able to do that without the presence of a conservator, he's happy."

And there's certainly a reason for Britney to be happy. In a report obtained by The New York Times, an investigative reporter said of the pop star during her conservatorship: "She is 'sick of being taken advantage of' and she said she is the one working and earning her money but everyone around her is on her payroll." So Britney had reason, both financially and independently, to feel free and happy.

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Britney Spears met Sam Asghari on the set of her "Slumber Party" music video, and in January 2017, they became Instagram official, according to People. The couple traveled all over the world and Asghari joined Spears when she performed in Japan in 2017. The model proved his steadfastness in 2019 when Jamie Spears suffered a colon rupture, per a later publication by People. Britney halted work to care for him and afterwards, admitted herself into an "all-encompassing wellness treatment" center to regroup.

An insider told People that Asghari was an asset in Britney's life. "There is no question that Sam is great for Britney," they said. "He has a very positive influence on her. He is very motivated to stay healthy and fit, and they often work out together."

When it came to the end of Spear's conservatorship, Asghari was hugely supportive. "I have always wanted nothing but the best for my better half, and will continue to support her in following her dreams and creating the future she wants and deserves," he told People. In September 2021, Spears and Asghari got engaged and she shared the news on Instagram. So, what did Kevin Federline have to say? His lawyer, Mark Vincent Kaplan, told ET: "Kevin is very happy for Britney and wishes both she and Sam a happy and full future together. It would seem to indicate that positive things are going forward for her as she takes more control of her life." Sounds like a lot of support.