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Fiona Apple – O' Sailor Lyrics 11 years ago
I'm undecided about you again
Mightn't be right that you're not here
It's double-sided, because I ruined it all
But also saved myself, by never believing you, dear

She’s re-hashing this relationship in her mind. She thinks she drove him away with her trust issues; she couldn’t allow herself to believe his feelings for her were genuine, so she thinks she ruined it. She thinks she may have saved herself more heartache in the long run, but isn’t sure.

Everything good, I deem too good to be true
Everything else is just a bore
Everything I have to look forward to
Has a pretty painful and very imposing before

She didn’t believe in him because he seemed to good to be true; nobody has treated her so well before. She can’t believe in him because she’s been hurt so many times before.

Oh sailor, why'd you do it
What'd you do that for
Saying there's nothing to it
And then letting it go by the boards

The chorus is questioning why he finally left. Why did you end it? How could it mean so little to you, that you’re letting it go?

I have too been playing with fifty-two cards
Just because I play so far from my vest
Whatever I've got, I've got no reason to guard
What could I do, but spend my best?

She says she has experience playing the game; she just isn’t very good at remaining aloof. She played her best cards on this guy, which I believe means despite her trust issues she went all in with her feelings and let him know it.

And after waiting, fighting patiently on my knees
All the other stuff tired itself out first, not me
And in its wake, appeared the touch and call
Of a different breed
One who set to get me wise, and got me there
And then, got me

She’s been single for a while and she was just starting to put herself out there again. When she met this guy who appeared different and treated her well, showed her how she should be treated, made her feel hope, and she started to let her guard down.

And what a thing, to know what could be instead
Oh, what a blessed curse; to see
It took the agenda from its place in my bed
Made a merry paramour of me

She learned how a man should treat her and how things could be. It is a blessing and a curse because he’s gone now and she knows what she lost. The way he treated her took her out of her own head and made her happy.

Oh sailor, why'd you do it
What'd you do that for
Giving me eyes to view it
As it goes by the boards

The last stanza shows that she is lamenting what is lost. You showed me how good things could be and then left anyway

* This information can be up to 15 minutes delayed.