The Walk of Shame

Simpson was rumored to have first hooked up with Maroon 5 frontman Adam Levine in 2004, while she was still married to Nick Lachey. In January 2006, the two reportedly spent the night at L.A.'s Chateau Marmont together. The next morning, Simpson was spotted wearing his T-shirt as she got picked up outside the hotel by her friend and assistant at the time, Cacee Cobb.