Six months after annulling her marriage to Alexander, Spears moved on with her backup dancer, who was still married to actor Shar Jackson at the time. After dating for a few months in 2004, the duo tied the knot in a surprise unofficial ceremony — they didn't have a prenup agreement, so it wasn't official for three weeks, per Us Weekly.
The pair welcomed two sons together, Jayden James and Sean Preston, and even went on to have their own reality show on UPN called "Britney and Kevin: Chaotic." However, as Spears's career took a turn for the worse, the two ended up pulling the plug on their marriage and split in October 2006, though their divorce wasn't finalised until July 2007.