With a brand spankin' new recording contract, Ashlee Simpson is ready to take her first steps in her new life. She waves goodbye to mom and dad and hello to her fabulous apartment and budding romance. Unfortunately, she quickly learns along with the good, comes the not-so-good...building a home, relationship and career is no walk in the park. Thankfully, mom is not far away, and she soon pays Ashlee a visit to give her a crash course in cleaning magic and relationship woes. But there are some things a girl has to learn on her own, like doing her own laundry and dealing with her boy-toy, Josh. Much of Ashlee's inspiration for her music comes from her beau, Josh. From sniffing each other's armpits to playing an intense game of bowling, these love birds seem to be having a ball. They cruise around in her Lexis by day and party by night. Josh also hangs out with Ashlee when she works with her music co-writers, which she finds a bit embarrassing, because her tunes are about him. Though as t

After breaking up with her boyfriend Ashlee travels to New York City. When she gets there she writes songs with her music producer. And while shes in New York, Ashlee buys a Christmas tree and pierces her ear.

Ashlee Simpson is starting to realize that being a rock superstar isn't as easy as it seems. Disagreements with her label and problems hitting the right notes in the studio have made Ashlee especially determined to create a successful album. The label decides to hook up Ashlee with a team of people to help write some songs until she begins to figure out her identity within the girly rock-pop scene. Ashlee flies out to Austin, Texas to appear in her friend Ryan's music video. An early call time and a slight hair disaster later, Ashlee lands on the set of Ryan's video where she shocks everyone, including Ryan, with a few surprises she's got stored up her sleeve. Ashlee pins Ryan up against a wall for a kiss, and that's not the end of the smoochin'--they don't stop when the director calls cut. By the end of the shoot, it looks like Ashlee may have scored herself a new boyfriend. Ashlee heads home to L.A. to return to work on her album, and arrives at the studio late as usual. ""I wanted to

Ashlee & Ryan officaly become an item. Ryan plays a song for Ashlee. And it ends up that Ashlee does not even know the song, that makes Ashlee mad.

Ashlee does her first photo shoot, and she ends not knowing what to wear. Ashlee is determined not to look too girly or like Jessica.

Ashlee and Jessica film their Pizza Hut commercial. Also Ashlee Performs Live at The Knitting Factory.

With Ashlee's cd about to be released and her tour about to start, Ashlee takes pictures for the cover of her cd.

Ashlee does a press tour for her new CD. She goes to New York and appears on many talk shows and radio shows. Also she learns that her CD, is selling like hotcakes. Meanwhile when she goes on the Today Show Nick is there. And when she goes to MTV she chats with P Diddy & Jay-Z.