"What Can You Lose?" is a quarrel that the poet has with himself.
What can you lose?
Only the blues.
Why keep concealing everything you're feeling?
Say it to her--what can you lose?
The speaker is miserable because he has not declared his love. But, because the writer is Sondheim, there isn't any easy solution. The song pivots:
Maybe it shows.
She's had clues, which she chose to ignore.
Maybe, though, she knows--
And just wants to go on as before.
(As a friend, nothing more.)
So she closes the door.
In other words, a declaration would just be a source of embarrassment. The beloved "doesn't want to hear it."
Once the words are spoken--
Something may be broken...
Leave it alone.
Hold it all in.
Better a bone--
Don't even begin.
With so much to win--
There's too much to lose.
An ambivalent semi-courtship is "just a bone"--just the scraps from a chicken dinner. But the scraps are better than an empty plate.
The last sentence revisits the first. "What can you lose?"--a cliched thought--is really a foolish question. The song has a "call-and-response" structure--very satisfying, even if you aren't fully aware of it as you're listening.
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