"If I Were Brave" by Shawn Colvin

From the album A Few Small Repairs 1996

The song starts in the Bailey/Sarah ice cream scene:

All the happy couples on their way to New Orleans
Reminding me of when we got along
They're only renting time and space to fill up with their dreams
And dreams are what they'll have when they have gone

How could it be that I was born without a clue to carry on
And still it is the same now I am older
Armed with just a will and then this love for singing songs
And minding less and less if I am colder

The song continues and the scene turns to Charlie, where the lyrics perfectly add to his situation and how he's feeling:

But I have this funny ache and it's burning in my chest
And it spreads just like a fire inside my body
Is it something God left out in my spirit or my flesh
Would I be saved if I were brave and had a baby

This part was edited out of the scene:

It was never clear what would come next but that's the risk and that's the test
And you were the only one so far to follow
And no one talks about when one might stop and need to rest
Or how long you sit alone before you stop looking back
It's like you're waiting for Godot
And then you pick your sorry ass up off the street and go...

The remaining lyrics finish the scene:

And what the hell is this, who made this bloody mess
And someone always answers like a martyr
Is it something you should know, did you never do your best
Would you be saved if you were brave and just tried harder

So now I ride the aught one thirtyfive to New Orleans
I float a mile above life's toil and trouble
A thousand lonely lifetimes I still wait and then go on
A clown to entertain the happy couples

Thanks to Tito for this transcription.
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