A meme on Facebook: random search songs in a personal library in answer to set questions. I used my iTunes's "Purchased" folder.

Some of the responses are alright:

When you wake up you say...
There's No Way Out of Here - David Gilmour

It's Friday, how do you feel?
Over the Rainbow - Judy Garland

Summer! The first thing you do...
Come Thou Fount - Nathan Tasker

When you're alone you think...
Where Have All the Flowers Gone - The Kingston Trio

Just failed your final! What do you say!?
Second Chance - Shinedown

This song describes your room
Greenback Dollar¹ - The Kingston Trio

Your crush just asked you out! You say...
I Got You - Split Enz

This song describes your personality
Tuesday's Gone² - Lynyrd Skynyrd

This song describes your future
Heaven - Live

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¹ Our room is painted green.
² Born on a Tuesday, "Tuesday's child is full of grace"