10 of the strangest celebrity hookups of all time (With Pictures)

3. Sandra Bullock, Jesse James

Nobody really understood why Sandra Bullock was so drawn to Jesse James when she started seeing him. Her Hollywood friends actually thought she was crazy, but it seemed like Sandra really loved him, considering that she went on to marry “the bad boy”. It would eventually come out in the press that Jesse hadn’t been faithful to Bullock, having had multiple affairs with different women behind her back, causing Bullock to separate from the love of her life, followed with a divorce.