This didn't work that well for mine, but I'm posting anyway because I want to read other people's attempts if they decide to try.
1. Put your music player on shuffle.
2. Press forward for each question.
3. Use the song title as the answer to the question even if it doesn't make sense.
Will you get far in life?
"Mr. Tiny Thong Bikini Wearer Guy" - Bud Light Commercial (Okay, we're off to a rockin' good start)
How do your friends see you?
"Show Me" - The Cure
Will you get married?
"Seventeen Again" - Annie Lennox
What is your best friend's theme song?
"The Man Song" - Sean Morey (HA HA HA HA HA. Oh man, sorry Rae.)
What is the story of your life?
"Lake of Fire" - Nirvana
What was high school like?
"Spiderweb" - No Doubt
How can you get ahead in life?
"Drive Me Wild" - Foo Fighters
What is the best thing about your friends?
"Gulf War Song" - Moxy Fruvous
What is today going to be like?
"Lovers in a Dangerous Time - Barenaked Ladies (really great cover, in case you haven't heard it)
What is in store this weekend?
"Fire Maple Song" - Everclear
What song describes you?
"Cigarette" - Ben Folds Five (Oh dear lord I hope that's not prophetic)
What song describes your grandparents?
"If You Could Only See" - Tonic
How is your life going now?
"So Much for the Afterglow" - Everclear (oh, har har.)
What song would they play at your funeral?
"Fine Again" - Seether (I hate the thought of funerals, and very nearly avoided this one altogether. Fortunately it doesn't match at all.)
How does the world see you?
"Keep 'em Seperated" - Offspring (I... I don't know what to say to this, other than HA. Unless it's talking about how Harrison was a shithole to grow up in, but most of us haven't, you know, gone to jail or killed ourselves)
Will you have a happy life?
"Iris" - Goo Goo Dolls (I see this is a happy song, so I approve)
What do your friends really think of you?
"We Are the Lucky Ones" - Bif Naked
Do people secretly lust after you?
"Meet Virginia" - Train
How can I make myself happy?
"I Saw the Light" - The Judds (Is my Winamp trying to tell me that Brian's cheating? Because I laugh at it if it is.)
What should I do with my life?
"1985" - Bowling for Soup (Travel back in time! That's what I should do to make myself happy!)
Will you ever have children?
"In the Middle of the Night" - Billy Joel (Again, funny, as most births occour way in the late late hours)