2. Britney Spears
One of Britney Spears’ most questionable choices was her relationship with backup dancer, Kevin Federline. The couple got married after only three months of dating (he left his former girlfriend,Shar Jackson, while she was still pregnant with their second child). They had two sons together, Sean and Jayden, before Britney filed for divorce after only two years of marriage.
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Their relationship attracted a lot of media scrutiny and was thought to be the beginning of Britney’s mental decline. Federline was awarded sole physical and legal custody of the boys, which he still has today.
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