Hollywood's Biggest Flirts

Credit: Mark Von Holden/WireImage

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September 11, 2011 - 11:10pm Chuck Sherman Jr
With a look like that he definitely likes boys.
July 31, 2011 - 10:55pm Chris Drake
His music is great. He, on the other hand is not.
July 22, 2011 - 8:17pm Heather Mize
He's so gross. I used to be SOOO in love with him. Yuck! His music and songs he writes are nothing like who he really is....nasty trash.

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John Mayer

The "Heartbreak Warfare" singer has dated some of Hollywood's most A-list stars, including Jennifer Love Hewitt, Jessica Simpson, Minka Kelly and Jennifer Aniston.