Ashlee Simpson has never been a predictable celeb. We met her when she was in Jessica Simpson's shadow but she showed her spontaneous side through her reality show The Ashlee Simpson Show and proved that blondes don't have more fun. Remember her dark and edgy look? Ashlee has always been a risk taker whether it's with her music or as an actress so her dating life definitely threw us for a loop! From preppy to rock stars -- she's dated an eclectic bunch of guys in her past. Take a peep now!

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