iPod shuffle meme nabbed from 3600sectors 

[1] What is your life going to be like in 5 years?
C'est la Faute a - Les Misérables Paris Revival Cast


[2] How is your love life going for you right now?
The Letter - Les Misérables 2009 London Cast


[3] What pisses you off the most about the opposite sex?
A la Volonté du Peuple - Les Misérables Paris Revival Cast (I'm noticing a theme already XD)


[4] What do your parents really think of you?
Til Him - The Producers OST


[5] What do you think about the world and its current state?
Drink With Me - Les Misérables Original Broadway Cast


[6] What is the worst thing that’s ever happened to you?
Fantine's Arrest - Les Misérables 10th Anniversary Cast


[7] What will your first/next time having sex be like?
Le Tango de Roxanne - Moulin Rouge OST


[8] What is your main goal in life?
In Too Deep - Sum 41


[9] What do the boys/girls at your school think of your looks?
Aftermath - Les Misérables 2009 London Cast


[10] What do you really want in life?
I'll Make A Man Out Of You - Mulan OST


[11] How are you going to get far in life?
Daddy's Eyes - The Killers


[12] What do say when you’re in a bad mood?
Twentieth Century Fox - The Doors


[13] What about when you are really happy?
Stars - Earl Carpenter


[14] What do think of yourself in general?
You Can Read My Heart - Daniel Boys


[15] What is your life’s theme song?
The Climb - Miley Cyrus (you got that one right!)


[16] What are you going to do this weekend?
Winter Wonderland - Peggy Lee (need to take my Christmas songs off already)


[17] How can you try and make yourself happy?
Try - Nelly Furtado


[18] What song will they play at your wedding?
Hand of Sorrow - Within Temptation


[19] Funeral song?
Turning - Les Misérables Original London Cast


[20] What or who makes you the most happy?
You Take My Breathe Away - Sarah Brightman


[21] What am I even doing on this earth?
The Threshold Of Her Heart - Dean Chisnall and Sabrina Aloueche


[22] How am I going to die?
Final Battle - Les Misérables 2009 London Cast


[23] What is some good advice?
Valjean Arrested/Valjean Forgiven - Les Misérables Original Broadway Cast


[24] What’s some advice you’d never take?
Ruby Don't Take Your Love To Town - The Killers


[25] Will you ever have children?
Something's Coming - West Side Story


[26] What is/was high school like for you or what will it be like?
Javert's Suicide - Les Misérables Original London Cast


[27] How are you feeling today?
Shaman's Blues - The Doors


[28] What’s your general outlook on life?
In God's Hands - Nelly Furtado


[29] What are your last words going to be?
You Make Me Real - The Doors


[30] What song is going to be stuck in your head all day?
In A World of My Own - Alice in Wonderland OST

Some of those are two weirdly accurate. HOW DOES IT KNOW?