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Jesse James: Sandra Bullock to Kat Von D

Rebound Time: 5 Months

Just weeks after Sandra Bullock won a best actress Oscar for her performance in "The Blind Side," her husband of almost five years (whom she gushed about in her acceptance speech), motorcycle man Jesse James, made a public confession and apology for his multiple infidelities. Bullock high-tailed it out of the marriage, and their divorce was finalized in June 2010. By mid-August, James had moved on to "L.A. Ink" star, Kat Von D, and the couple became engaged in January 2011. But history quickly repeated itself as Kat called off her engagement to Jesse in the fall. The straw that broke the tattoo artist’s back? Finding out he'd cheated with 19 girls over the course of their relationship!

(CREDIT: Getty Images)
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