Steve-O and Elisabetta Canalis

When: January-April

In the wake of her break-up with actor George Clooney, model Elisabetta Canalis began dating Jackass star Steve-O. Yep, Canalis went from dating the former Sexiest Man Alive to dating someone who first became famous for swallowing and then regurgitating a live goldfish. And the kicker here: he dumped her! Reportedly, Elisabetta's hard-partying ways conflicted with Steve-O's newly sober lifestyle, something he takes very seriously.