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.

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 brings a few friends with her to relieve some stress. So on SN Day, Ashlee wakes up to a raspy voice. So she heads on over to the SNL studios and so she starts to worry about her voice, even though she has her voice coach with her. Flustered and overwhelmed, Ashlee considers her options. It is suggested that she sing with a backing track, and Ashlee is left to ponder her quickly approaching performance. To be continued...

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 around about what happened at SNL, so then later she sings her song ""Autobiography."" Ashlee then goes to a radio station to be interviewed. So while she is in Pennsylvania she performs at different high schools. So after she flies out to LA to celebrate Halloween with her Family/Friends. And then Ashlee, Ryan, and their friends go out to Trick or Treat. Ashlee then also goes to Best Buy to sign autographs and chat with fans.

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 huge black limo. Their surprise destination turns out to be Medieval Times, where they will celebrate and watch knights in shining armor joust. After her Birthday she decides to chop off some of her hair, only to dissapoint her mom. Ashlee then goes to a Pilates studio to get in shape for her upcoming video shoot for ""La La."" Ashlee finds out that she has been chosen as one of Entertainment Weekly's breakout stars of 2004, and attends a photo shoot for the spread.

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 room in the house. Ashlee also does TRL after that she does a couple of radio interviews, Ashlee is off to Motor City for Detroit's Hob Wobble Gobble Thanksgiving show.

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 also wins the Billboard for New Female Artist of the Year.

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 holidays by preparing and serving dinner to homeless youth. To celebrate the holidays and to show her band her appreciation she takes them out to dinner.

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 see's girls flirting with Ryan, so she gets jelous, but other then that it turned out to be a great night. So after Ashlee flies to Miami so she can perform at the Orange Bowl.

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 doctor informs Ashlee that the acid reflux is getting worse. Also Ashlee and her band go to Europe to to do press and perform on the UK music show 'Top of the Pops.'

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 occur when Ashlee has a problem with her earpiece and Joe is worried about the guitar solo sounds. Then later Ashlee gives the thumbs up to start and the whole place was full and the show was great.