2005

January

 * January 4: Ashlee performs "La La" at the Orange Bowl halftime show; at the end of the performance booing is heard from some of the spectators.
 * January 6: The "Pieces of Me" single is certified platinum by the RIAA.
 * January 7: Top of the Pops performance of "La La" airs. (U.K.)
 * January 8: CD:UK performance of "La La" airs. (U.K.)
 * January 12: After an interview, Simpson performs the song on Today with Des and Mel. (U.K.)
 * January 15: Top of the Pops Saturday performance of "La La" airs. (U.K.)
 * January 16: Popworld performance of "La La" airs. (U.K.)
 * January 24: "La La" CD single released in the U.K.
 * January 26: The second season of The Ashlee Simpson Show begins airing in the U.S.

February

 * February 7: Simpson appears on TRL to talk about her upcoming tour, as well as other things.
 * February 10: The second season of The Ashlee Simpson Show debuts on MTV Canada.
 * February 16: Tour begins in Anaheim, California.
 * February 18: Second date of tour in Universal City, California.

March

 * March 29: "La La" is certified gold by the RIAA.
 * March 30: Last (tenth) episode of the second season of The Ashlee Simpson Show airs in the U.S.

April

 * April 20: Tour ends in Grand Prairie, Texas.
 * April 24: Ashlee is shown having a trick played on her in an episode of MTV's Punk'd.

May

 * May 3: Ashlee shows off a new hairstyle&mdash;shorter, with a reddish-blonde color&mdash;at a Candie's event.

June

 * June 19: Ashlee performs "La La" at the MuchMusic Video Awards, and also shows off another new hairstyle, this time fully blonde and longer than her previous style.

August

 * August 26: The movie Undiscovered is released.
 * August 31: Ashlee begins shooting her "Boyfriend" video (shoot continues on September 1).

September

 * September 6: "Boyfriend" officially hits radio.
 * September 12: "Boyfriend" video debuts on Making the Video.
 * September 13: Ashlee appears on TRL for the premiere of "Boyfriend".
 * September 14: "Boyfriend" debuts on TRL countdown at #9 (moves up in the following days)
 * September 21: Ashlee begins a short tour with a show in Portland, Oregon.

October

 * October 3: Simpson celebrates her 21st birthday in Las Vegas. She also performs. A show about her birthday, Ashlee Simpson Live and Legal, airs on MTV later in the month.
 * October 8-9: Simpson appears on Saturday Night Live for a second time, this time successfully. She sings "Catch Me When I Fall" and "Boyfriend".
 * October 18: U.S. release date of Ashlee's second album, I Am Me.

November

 * November 1: Simpson appears on MuchMusic's MuchOnDemand in Canada.

December

 * December 15: I Am Me certified platinum by the RIAA.
 * Mid-December: Simpson collapses due to exhaustion after performing in Japan and is briefly hospitalized. Afterwards, she takes some time off to rest.