1. Britney Spears and Charlie Ebersol
Britney Spears has never really had luck with men. Or, wait. Let’s take that back. She did have a good run with Justin Timberlake — before she decided to allegedly cheat on him, leading him to pen the song Cry Me A River. The songstress would go on to fall in love with Charlie Ebersol, but the relationship didn’t even last a year before the twosome would end up calling off their brief romance with one another. It’s unfortunate on so many levels; Britney keeps introducing all of these men to her children, who end up being dumped every other month or so. She needs to get it together.
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