Just close your itunes, open it again and don't click anything. Just press shuffle then play, and let itunes decides you life.
Then, fillin the songs in order according to these categories...

Opening credits:
Waking up:
First date:
Falling in love:
Love scene:
Fight scene:
Breaking up:
Getting back together:
Life's okay:
Mental breakdown:
Driving:
Flashback:
Partying:
Long night alone:
Death scene:

Here's mine:

Opening Credits:  "Rum Runner" -The Town Pants

Waking up: "Kaze no Machi e" -Tsubasa Reservoir Chronicles

First Date: "Butterfly" from DDR

Falling in Love: "We are the Champions" -Queen

Love Scene: "Uptown Girl"-Billy Joel

Fight Scene: "Ugly Baby" -Stephen Lynch

Breaking Up: "Crazy ex-girlfriend" -Miranda Lambert (how appropriate!)

Getting Back Together: "I Am" -Bon Jovi

Life's Okay: "Gin & Milk"-The Town Pants

Mental Breakdown: "Unidentified Friend" -The Town Pants

Driving: "The More You Ruv Someone" -Avenue Q

Flashback: "As Long As You're Mine" -Wicked

Partying: "Imperfection" -Saving Jane

Long Night Alone: "A Man For All Seasons" -Robbie Williams, from the Johnny English soundtrack

Death Scene: "No Tomorrow" -Orson

Closing Credits: "Story of my Life" -Bon Jovi

Heh, the first time I tried that I got "March of Witch Hunters" from Wicked. Fun, fun stuff.