8. Katy Perry – Russell Brand
Katy Perry has definitely dated some attractive men, but she also has made some highly questionable choices as well. For instance, Katy married actor/comedian Russell Brand in 2010, and despite their differing looks and unlikely success as a couple, they stuck together for a few years before divorcing in 2014. Apparently, Russell, who was previously a known drug addict, announced he wanted a divorce via text message to Katy, which seems shocking considering how far out of his league Katy was to begin with. After Russell, she also made a memorable MTV Video Music Awards appearance with the out-right dreadful Riff Raff. Luckily, it didn’t seem as if the two were officially dating (though it was never truly determined), and rather just hoping to show off their matching denim outfits, ala Britney Spears and Justin Timberlake.
SEE ALSO: The 10 most revealing dresses in red carpet history (With Pictures)
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