But after having had a taste of marriage, Britney deemed herself ready for the main course. She met dancer Kevin Federline in April 2004 and, despite the fact that he was expecting a child with barely-ex-fiancée Shar Jackson at the time, they were engaged by July.
While in hindsight it’s obvious that having a reality show with “Chaotic” in the title is a bad sign, back then…who knew?!
Brit and K-Fed had a marriage ceremony on Sept. 18, 2004 (their union was legalized three weeks later after they figured out their prenup), son Sean Preston was born a year later and son Jayden James arrived a year after that. In November 2006, Spears filed for divorce.
“Instead of following my heart and doing something that made me really happy, I just did it for the idea of everything,” she mused in the 2008 MTV documentary Britney: For the Record.
The rest is upside-down-world history. Newly separated, Britney started behaving (more) erratically, partying heavily, walking into a barber shop and shaving her own head, making late-night CVS runs with the paparazzi in hot pursuit, etc. She spent about a month in rehab in early 2007 (leaving and then returning when Federline said he’d raise custody issues if she didn’t complete treatment.
Spears did briefly lose custody of the kids in January 2008 when she was hospitalized on a 5150 psychiatric hold, a scary episode that resulted in her affairs being placed in a conservatorship overseen in part by her father—an arrangement that exists to this day.
Her career comeback would take some time, but Spears made sure to focus on getting well enough to be with her boys again right away, and she and Federline eventually turned into amicable co-parents. He has since had two more children with wife Victoria Prince and is now a father of six.
“Obviously, things didn’t work out the way that they were supposed to [with Britney],” Federline reflected to Entertainment Tonight in 2016. “But everything’s OK, you know, like, life happens.”