"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 revisit...