Put your iTunes/Winamp/POS WMP on random, then ask it each question out loud before going to the next song. Record what song it jumps to as the answer.
Question: What do you think of me, O iTunes Player full of mp3s?
FOR THE WORKFORCE DROWNING - THURSDAY
Question: Will I have a happy life?
FULLFILLING - SLICK SHOES
Question: What do my friends really think of me?
WITHOUT ME - EMINEM
Question: Do people secretly lust after me?
THREE SIMPLE WORDS - FINCH
Question: What should I do with my life?
YOU'RE DEAD - ALKALINE TRIO
Question: Why must life be so full of pain?
NOW YOU KNOW HOW I FEEL - MIKE SCHUETTE
Question: How can I maximize my pleasure during sex?
HIT THE FENCE - THE TRANSPLANTS
Question: Will I ever have children?
IN YOUR HANDS - THRICE
Question: Will I die happy?
SUICIDE PARTY - VENDETTA RED (oh god)
Question: Can you give me some advice?
GET IN MY CAR - 50 CENT
Question: What do you think happiness is?
PAIN FOR PLEASURE - SUM 41
Question: What's my favorite fetish?
ROSA PARKS - OUTKAST