Put iTunes on shuffle and "answer" the questions based on the song that comes up. Adding the lyrics and commentary is unnecessary, but I highlighted some parts for those who are unfamiliar with the songs.
Question: What do you think of me, iTunes?
Answer: Answer - Sarah McLachlan (my iTunes is clingy)
['Cause I can only tell you what I know,
That I need you in my life.
When the stars have all gone out,
You'll still be burning so bright.]
Question: Will I have a happy life?
Answer: Unsung - Vanessa Carlton (magic 8 ball says "outlook not good")
[Well I am crying,
You aren't trying,
And I am melting away.
I wait for the words on the tip of your tongue.]
Question: What do my friends really think of me?
Answer: Sweetest Goodbye/Sunday Morning - Maroon 5 (they love me...aww)
[I'll never leave you behind,
Or treat you unkind,
I know you understand.]
Question: Do people secretly lust after me?
Answer: I Heard It Through the Grapevine - Marvin Gaye (even the title makes sense)
[Ooh, I bet you're wondering how I knew,
About you're plans to make me blue.]
Question: What should I do with my life?
Answer: Allentown - Billy Joel
[So the graduations hang on the wall,
But they never really helped us at all.
No they never taught us what was real,
Iron and coke...
And chromium steel.]
Question: Why must life be so full of pain?
Answer: Kryptonite - 3 Doors Down (I think it's blaming me...)
[I watched the world float to the dark side of the moon,
After all I knew it had to be something to do with you.
I really don't mind what happens now and then,
As long as you'll be my friend at the end.]
Question: Will I ever have children?
Answer: Zak and Sara - Ben Folds (apparently two kids...one a sensible boy, and the other a psychotic girl)
[Zak called his dad about layaway plans,
And Sara told the friendly salesman that:
"You'll all die in your cars,
And why's it gotta be dark?
And you're all working in a submarine."]
Question: Will I die happy?
Answer: Feelin' the Same Way - Norah Jones (I will die feeling the same as I do now. Wow...that's something to look forward to)
[And I'm feelin' the same way all over again,
Feelin' the same way all over again,
Singin' the same lines all over again,
No matter how much I pretend.]
Question: Can you give me some advice?
Answer: Eat the Rich - Aerosmith (heh. Perhaps I should stop being a tool of a capitalist society)
['Cause I'm sick of your complainin'
About how many bills,
And I'm sick of all your bitchin'
'Bout your poodles and your pills.
Eat The Rich
There's only one thing that they are good for.]
Question: What do you think happiness is?
Answer: Bad - U2
[If I could, through myself,
Set your spirit free,
I'd lead your heart away,
See you break, break away
Into the light
And to the day.]
Question: What's my favorite fetish?
Answer: You've Got A Friend - Carole King
[You just call out my name,
And you know wherever I am,
I'll come running to see you again.]
Question: Am I complete freak?
Answer: Proud Mary - Creedence Clearwater Revival (I think that's a "yes")
[Cleaned a lot of plates in Memphis,
Pumped a lot of 'pane down in New Orleans,
But I never saw the good side of the city,
'Till I hitched a ride on a river boat queen.]