The “Toxic” songstress met Federline in 2004 — the same year she was briefly married to childhood friend Jason Alexander for 55 hours.
“I met her at a club in Hollywood, Joseph’s. Our eyes met and that was it. We just hit it off right away,” the dancer recalled in 2008. “I was madly in love with her. Everything just seemed so right. I didn’t see it as too fast or too slow.”
Spears began documenting her romance with Federline via a handheld camera, later selling the footage to UPN. Britney and Kevin: Chaotic, which aired five episodes in 2005, included their surprise September 2004 nuptials. (Their union became legal on October 6, 2004, when they obtained their marriage license.)
“I think my mom was dumbfounded,” the singer admitted on the reality show, referring to mom Lynne. “She couldn’t believe what was going on, and when she realized it, she was so cute. She didn’t know what to say.”
Spears added, “It wasn’t the big, traditional wedding. It was cool and it was nice and special and small, and I liked it a lot.”
The twosome didn’t waste much time starting a family, confirming the Grammy winner’s pregnancy in April 2005.
“A lot of people think you should wait till you’re older to have kids. I’ve had a career since I was 16, have traveled around the world and back, and even kissed Madonna!” Spears wrote on her website shortly after her nuptials. “The only thing I haven’t done is experience the closest thing to God, and that’s having a baby. I can’t wait!”
Spears gave birth to son Sean Preston in September 2005. “We are ecstatic to announce the birth of our son,” the pair said at the time. “Everyone is happy, healthy and doing wonderful. Thank you all for your love and well wishes!”
Less than one year later, she announced that she was pregnant again.
“Don’t worry Dave, it’s not yours,” Spears joked on the Late Show with David Letterman in May 2006.
The pair welcomed son Jayden Federline in September 2006. Two months later, it was over for Spears and Federline, citing irreconcilable differences. They finalized their divorce in July 2007.
Scroll through for a closer look at Spears and Federline’s former romance: