What We Know About Britney Spears' Relationship With Kevin Federline

When considering the most memorable Hollywood couplings in history, you've got Sonny and Cher, Brad and Angelina, Ben and Jennifer, and ... Britney and Kevin.

While Britney Spears and Kevin "K-Fed" Federline's time together lasted less than three years, their legacy as a couple lives on. Who can forget their whirlwind romance that led to an engagement and a surprise wedding within the same year? The two shared some wild times — with paparazzi there for most of it. You can't forget their short-lived reality series, "Britney & Kevin: Chaotic," which documented their romance through home video footage (Britney later referred to it in an interview as "the worst thing [she's] done in [her] career").

Spears and K-Fed, however, will always share one thing — well, actually two — their sons, Sean Preston and Jayden James, born one year apart in 2005 and 2006 (via Cosmopolitan). Over the years, the former lovebirds have engaged in tumultuous custody battles. Yet, since then, they've managed to successfully co-parent, with K-Fed even being quoted in the media for his support of his pop star ex-wife. But what exactly has their relationship been like at various points, and where do they stand today? With a since-deleted Instagram post from April 2022, where the singer opened up about K-Fed's alleged mistreatment of her, we have to wonder if there's more to the story than even the most die-hard Spears fans know.

In 2004, Britney Spears met backup dancer Kevin Federline at the Hollywood club, Joseph's Cafe — not long after her 55-hour-long marriage to childhood friend Jason Alexander, whom she wed in Las Vegas (per Newsweek). "Our eyes met and that was it. We just hit it off right away," K-Fed told People in 2008. Years later, he described to Us Weekly that what he loved about the pop star were her Southern traditions and "normal life values."

At the time of their meet cute, however, Spears' new man was expecting his second child with his then-fiancée, "Moesha" actress Shar Jackson (via People). Jackson shared her thoughts on the unfavored situation at the time, saying, "It wasn't like just breaking up a relationship. It was like breaking up a family." An exclusive interview with MTV News later seemed to prove that she wasn't really upset after all. "If you read anything negative that I'd supposedly said, it's probably not true," Jackson said. "I believe that ... everything happens for a reason, the way it's supposed to happen. I'm cool with that, so I don't have any bad feelings."

Britney Spears' relationship with Kevin Federline seemed to go at full speed pretty quickly, with the two photographed regularly by paparazzi. "I learned real fast how much of a whirlwind the press and everything was," K-Fed told People.

Spears was so enamored with her new beau that she invited him to join her on tour in March 2004 — a jab at her ex-boyfriend, Justin Timberlake, according to E! News. However, shortly thereafter, an injury forced Spears to cancel the remainder of her shows. While resting at home, she surprisingly proposed to her backup dancer boyfriend. Months later, he returned the question with a proposal of his own.

Of their wild courtship, K-Fed explained that, regardless of how it appeared to the public, to them, they were just two people in love. "Everything just seemed so right. I didn't see it as too fast or too slow," he told People. 

In 2005, Britney Spears and Kevin Federline shared an inside look at their love in a documentary-style TV series titled "Britney & Kevin: Chaotic." Though on-air for only one season, the show's few episodes did provide the public with candidly intimate details.

Even Spears regretted having shared such personal moments with the world, telling The Telegraph in 2013, "I would never do something like that again. Actually, that was really bad. That was probably the worst thing I've done in my career." And, if Spears said it's bad, you know it's bad.

Shortly following that interview, Entertainment Weekly shared its thoughts on the infamously short-lived reality show. The magazine agreed with Spears, noting that the series showed only her superficial side, that K-Fed appeared to be nothing more than "Britney's boy toy," and that it overly shared moments otherwise saved within a relationship. "Some moments with your significant other should stay private," it noted.  

The pair's wedding turned out to be just as talked about as their whirlwind relationship. According to People, Britney Spears and Kevin Federline had planned to wed on October 16, 2004, in a lavish ceremony and reception at a resort in Santa Barbara, California — they had even sent out 100 invitations.

But with increasing stress and media attention, the couple opted for a more intimate — and secret — "rose-scented" gathering of just 27 friends and relatives in early September at a private home in Studio City. In fact, the guests had no knowledge of the purpose behind the meet until just before the ceremony. The two even planned for everyone's gowns and tuxedos to be brought conspicuously to the house, including Spears' $26,000 Monique Lhuillier strapless gown (per Us Weekly).

In the end, the twosome largely did their wedding how they wanted. "I just thought it would be too much if we had done it when we were supposed to. It became this huge thing ... That's why I wanted to sneak and do it our little way," Spears said (per People).

The celebration also included a night out clubbing, and a bachelorette party at the Fairmont Miramar Hotel followed by a spa day, while the guys hit the golf course.

Britney Spears had long wanted to be a mom, having discussed her plans to become a young mother around the time of her wedding to Kevin Federline. "I want to be a young mom," she told People in 2004. "I can see myself as a mom. Next year at 23, I am so there."

It turns out that the pop star manifested her own destiny. A year after her surprising wedding to K-Fed, Spears gave birth to her first son, Sean Preston. A year later, in late 2006, the couple welcomed a second son, Jayden James, per Woman & Home.

Spears has spoken out about her experience with motherhood over the years. For example, in one Instagram post, she wrote, "I had my babies very young ... at all the pools we went to on tours, all the babies flocked to me because I always brought the most toys."

Just weeks after giving birth to her second child, Britney Spears' life seemed to dramatically change. In November 2006, People reported that the singer had filed for divorce from Kevin Federline, citing the common "irreconcilable differences." While some fans weren't shocked due to the brief timeframe of their courtship, K-Fed revealed he had been completely "blindsided" by the revelation, he later told People in an exclusive interview. "I was trying to work stuff out with her, and she didn't even talk to me or anything," he said.

Sources told the magazine the couple had been experiencing problems during Spears' pregnancy with Jayden, and that the marriage had reportedly become more "strained" after their first son was born. Leading up to the split, People claimed the two hadn't been seen together in weeks, and that Britney was absent from events to promote K-Fed's then-newly released rap album.

The report also indicated that K-Fed had been spending more time away from his young family. Apparently, Spears' "last straw," according to one source, was when her then-husband left for Las Vegas with friends, while Britney, having just given birth weeks before, remained at home.

After Britney Spears filed for divorce from Kevin Federline, a point of contention was the custody agreement over their two young sons. TMZ noted that, in the initial filing, Spears had requested legal and physical custody, with her ex having visitation rights. She then hired powerful Hollywood attorney Laura Wasser, who is known for representing other high-profile celebrity divorces, including that of Nick Lachey, Angelina Jolie, and Kiefer Sutherland. According to the tabloid, Spears and K-Fed already had a prenup set in place. When it came to spousal support, Britney unsurprisingly declined while requesting each party pay their own legal fees. 

Spears' ex, however, did not accept her request for sole custody and fought for more time with his kids. When the divorce was finalized in June 2007, the separated couple settled on a joint custody agreement of 50/50, according to StyleCaster.

Britney Spears and Kevin Federline's joint custody agreement would not remain in place for long. In October 2007, K-Fed was granted temporary sole custody of the boys, as StyleCaster reported, because of, as he claimed, his ex-wife's "habitual, frequent and continuous use of controlled substances and alcohol."

As we all remember, Spears fell on dark times after her divorce. Reports of the pop star's bizarre behavior surfaced, from driving with her infant boys on her lap to shaving her head and attacking the car of a photographer with an umbrella, before eventually checking into rehab. Britney, however, continued to surround herself with shady characters while cavorting regularly in a pink wig, before enduring a disappointing public reaction to her 2007 MTV Video Music Awards performance, per People.

By early 2008, a judge awarded K-Fed sole custody of their two sons, per The Guardian, after an hours-long standoff at Spears' Beverly Hills home. (At the time, Britney was arrested and taken by ambulance and put on an involuntary "5150 hold").

If you or someone you know is struggling with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.

Shortly after Britney Spears lost custody of her sons, she was placed under a now-infamous legal conservatorship ordered by her father, Jamie Spears. Once the order took effect, it seemed as if the pop star had put her troubled past behind her. By July 2008, as People had reported, Britney's visitation rights were extended from the two weekly visits and one overnight weekly visit she had been granted. Of the extension, her attorney said, "Britney's doing great. She's very pleased [with the settlement]. The kids are with her right now."

By 2013, Spears and Kevin Federline were said to have become amicable co-parents for the sake of their sons. In March of that year, they were even photographed together smiling and talking at their sons' soccer game, per an Us Weekly report.

Two years later, K-Fed spoke to "Access Hollywood Live" of their situation. "We have two beautiful children. The way that everything has turned out, everybody's happy. Coparenting is going great. I can't complain" (via Us Weekly). And, in 2016, the exes were seen laughing together at their sons' football game.

While the exes did eventually put the past behind them for the sake of their two children, it wasn't always easy. In fact, there were many times when Britney Spears and Kevin Federline weren't even speaking.

A March 2011 report from Us Weekly shared that the former couple did not speak to each other at son Sean's Little League game. Apparently, as sources claimed to the magazine, Spears kept to herself, talking with friends, her then-partner and former manager, Jason Trawick, and her younger son, Jayden. "Victoria [Prince, K-Fed's then-girlfriend] was sitting in the front row right next to Britney and Jason, but she kept to herself and talked to friends," a source noted.

Another source told the magazine that the exes avoided each other throughout the entire game, even as it ended, saying, "He and Britney didn't come near each other until the end of the game, and even then, they stayed separate and didn't talk."

In August 2013, Kevin Federline remarried, this time to his longtime girlfriend, Victoria Prince. However, as the National Enquirer noted at the time, Britney Spears was said to have supposedly been less than thrilled. In fact, she reportedly "screamed uncontrollably" and "collapsed in tears," according to a source. "The wedding caught her by surprise. She wasn't invited and she didn't even get a call from Kevin to let her know he was marrying Victoria."

At the time, Spears reportedly had a new boyfriend, David Lucado, whom she began seeing after she split from ex-fiancé Jason Trawick. By this time — even though K-Fed had been with Prince, whom he shared a daughter with, for several years — sources claimed to the publication that for a long time Spears supposedly had a "fantasy" of reuniting with her ex-husband. According to the source, "the wedding has crushed her, and she's angry that she definitely won't be getting Kevin back."

All seemed well on the co-parenting front until May 2018 when Kevin Federline filed a legal request to increase his child support payments. The amount requested was reportedly said to be "at least three times" the $20,000 monthly payment he was already receiving, according to court documents (via The Blast). K-Fed cited a significant change in the kids' needs among his reasons.

The backup dancer-turned-rapper-turned DJ reported a monthly income of about $3,000 at the time, which he claimed to be less than 1% of Britney Spears' $34 million annual earnings (per Forbes) — an increase partially due to her highly successful Las Vegas residency. "I am no longer able to perform as a dancer due to my age," K-Fed claimed in the official filing. "[I'm] less in demand than I was in 2008." He explained further that when the original agreement was made in 2007, Britney had not been working due to her mental health.

The media and the public largely labeled the move a "shameless money grab," while a source told Us Weekly that Spears and K-Fed's relationship had become "strained" and that "she's angry Kevin is asking for more money because she pays for everything."

However, by September 2018, the issue had been resolved, with Spears agreeing to pay her ex a higher monthly amount of approximately $35,000, according to Us Weekly.

Regardless of all that transpired between them, Kevin Federline has appeared to be supportive of Britney Spears, at least according to various media reports.

For example, in April 2019, K-Fed showed his support for Spears amid reports she had sought treatment at a mental health facility after canceling her follow-up Las Vegas residency, "Domination." Spears had cited stress over her father's health issues in a post to Instagram (via Us Weekly). According to his attorney, Mark Vincent Kaplan, "Kevin commends Britney for recognizing that she needs to take a step back and that she is taking the reasonable steps to deal with her situation in a responsible way" (via The Blast). During this time, the boys remained primarily in the care of their father and stepmother.

Later, in June 2021, after Britney testified in court during her hearing to end the nearly 13-year-long legal conservatorship that had been in place, K-Fed's attorney again shared his client's thoughts on his ex in a statement to People. "The best thing would be for their mom to be healthy and happy," the statement read. "And if either of those things aren't true, it doesn't provide for the best setting for custody to be exercised."

Despite Kevin Federline's supposed public support for Britney Spears over the years, it seems she may not be totally ready to close the book on their past. In April 2022, BuzzFeed reported that Britney had revealed in a since-deleted Instagram post that her ex-husband refused to see her when she flew to see him while pregnant. She added that the real reason she filed for divorce was that her team told her that he would leave her if she didn't leave him first. She went on to explain that "since [she] hadn't seen him in a while [she] already knew it was over."

The post garnered support from her fans, with some suggesting she may go more into detail about their turbulent past in her upcoming tell-all book. Yup, that's right. In February 2022, Page Six was the first to report that the pop singer had signed a $15 million book deal with Simon & Schuster for a revealing memoir about her life, her career, and her family. The news came only several months after the declared end of her 13-year conservatorship. Spears had become especially vocal about her miscarriage. On Instagram, she teased the writing of her upcoming book, saying, "Shall I start from THE BEGINNING???" (via Billboard). 

We hope so!