I'd try this, but there is far too much AC/DC in my rotation.  I don't want to know the question "Big Balls" is the answer to.  Also a bit scared of Nine Inch Nails.

1 - How does the world see me?
'You're Easy On The Eyes" Terri Clark

2 - Will I have a happy life?
"Streamline Woman" Muddy Waters

3 - What do my friends really think of me?
"Sweet Sweet Baby" Aretha Franklin

4 - Do people secretly lust after me?
'Head Like A Hole" NIN

5 - How can I make myself happy?
"Lips of an Angel" Hinder

6 - What should I do with my life?
'Nothing But Flowers" Talking Heads

7 - Why should life be full of so much pain?
"Love Stinks" J Geils Band

8 - How can I maximize my pleasure during sex?
"Teen Angst" Cracker
Yikes..it could be worse I guess, it could have been 'Lawyers Guns and Money" by Warren Zevon...or is that what comes next?

9 - Will I ever have children?
'Lonely No More" Rob Thomas

10 - Will I die happy?
"Nobody's Baby" Sharon Jones & The Dap Kings

11 - What is some good advice for me?
"Cause Cheap is How I Feel" Cowboy Junkies

12 - What is happiness?
'Hold On I'm Comin'" Sam & Dave

13 - What is my favorite fetish?
'Money For Nothing" Dire Straits

14 - How will I be remembered?
'I Know What Boys Like" The Waitresses

"It was an ancient rule of Hawaiians that no one should hurt another bodily, or through theft of goods or through injury to feelings.These were the only sins."

1 - How does the world see me?
"Fuck with me and find out" ~ Wesley Willis(1)

2 - Will I have a happy life?
"Don't look back" ~ Boston

3 - What do my friends really think of me?
"You don't know how it feels" ~ Tom Petty

4 - Do people secretly lust after me?
"Talk Dirty to me" ~ Poison

5 - How can I make myself happy?
"That's just the way it is" ~ Bruce Hornsby

6 - What should I do with my life?
"The Wanderer" ~ Del Shannon

7 - Why should life be full of so much pain?
"In a sentimental mood" ~ John Coltrane

8 - How can I maximize my pleasure during sex?
"Black Betty" ~ ZZ Top

9 - Will I ever have children?
"Double Vision" ~ Foreigner(2)

10 - Will I die happy?
"Knowing me, knowing you" ~ ABBA(3)

11 - What is some good advice for me?
"You're so vain" ~ Carly Simon

12 - What is happiness?
"Small Town Girl" ~ Journey (4)

13 - What is my favorite fetish?
"Purple Haze" ~ Jimi Hendrix

14 - How will I be remembered?
"Rock the Casbah" ~ The Clash

(1)That does explain why most of the bus and subway people don't screw with me.
(2)Does this mean I am destined for twins?
(3)Fuck. That song pretty much means I'm headed for the abyss.
(4)Thankfully it was not #13, but I still feel dirty.

Ok, here goes:

1 - How does the world see me?
"Ne me quite pas" - Nina Simone

2 - Will I have a happy life?
"Help" -- Beatles cover - Howie Day

3 - What do my friends really think of me?
"Tomorrow We'll see" -- Sting

4 - Do people secretly lust after me?
"Pictures of you" -- The Cure

5 - How can I make myself happy?
"Wrek tha discotek" -- Roger S./Soulson

6 - What should I do with my life?
"You Learn" -- Alanis Morisette

7 - Why should life be full of so much pain?
"Here comes santa claus" -- The Mills Brothers

8 - How can I maximize my pleasure during sex?
"Christmas in New Orleans" -- Satchmo

9 - Will I ever have children?
"Santa Clause came in the spring" -- Benny Goodman

10 - Will I die happy?
"Maximum Overdrive" -- M.O.R.P.H.

11 - What is some good advice for me?
"Don't Shoot shotgun" -- Def Leppard

12 - What is happiness?
"Prove my Love" -- Violent Femmes

13 - What is my favorite fetish?
"Benjamin" -- Veruca Salt

14 - How will I be remembered?
"Put your dreams away" -- Sinatra

The streak of Christmas music in the middle is inexplicable, it must be a sign.  Sadly, not a single AC/DC song popped up.