
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…
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…
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…

In the Second Season Opener, Ashlee moves to her new home. Ashlee's best friend/roommate fails to show up on moving day, which causes quite a ruckus. Also Ashlee Heads to the Big Apple for her appearance on Saturday Night Live. So she…
After the humiliation on Saturday Night Live. Ashlee decides to do The Radio City Music Awards, but first she decides to call TRL and explain her side of the story. When she begins performing at The Radio City Music Awards she jokes…
It's Ashlee's 20th Birthday! And her friends come to her and suprise her with a cake. Also her friends are taking her out, but they won't tell her where they're going. They all dress up in long pink, old fashioned dresses and get into a…
When Ryan comes back from his tour, Ashlee is excited for him to be back. But there is a problem Ashlee is very busy and she has no time to spend with him. Also Ashlee's interior decorator stops by and Ashlee goes over her plans for each…
Many things are going for Ashlee right now, she is filming a movie, getting ready for the Billboard Awards, doing shows and talking to reporters. And also, her relationship with Ryan Cabrera is beginning to hit some roadblocks. Ashlee…
Ashlee & Ryan are reunited in Boston at Jingle Ball. Ashlee is disappointed that he isn't more excited to see her. The relationship is hitting a sour note due to scheduling conflict. And later Ashlee returns to LA and they spend their…
Ashlee & Ryan pack their bags and head over to New York City for off to New York to celebrate an ""Iced Out"" New Year's Eve at MTV's famous Times Square bash. Ashlee takes her friends shopping for something to wear tonight. At the party…
Ashlee is performing at the Orange Bowl, without a working ear piece, making it impossible for her to hear herself. So that causes Jessica to worry. Then Ashlee and her mother visit the doctor to check up on her acid reflux. And the…
Ryan gets Ashlee a puppy named Blondie. Because Ryan got her a new puppy, Ashlee gets Ryan a hamster. Ashlee is also prepping for her upcoming tour. So she heads on over to the gym to get her body in tip-top condition.
Ashlee and her band go through an intense, two-week rehearsal period to prepare for their very first headlining tour. Joe (Ash's Dad) gives the band a speech about how serious and important this tour is for Ash's career. But problems…
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