affair | Reviewer: meesh | 11/21/07

i think this guy is cheating on his wife with a younger, slightly troubled girl. I think the song characterizes two people really well, especially the girl, in all those details like wearing many hats every time, but i also think that her characterization helps us understand what their relationship is like because he is the narrator and cannot fully account for the relationship. the effect it's having on her is much different than the effect it's having on him. other than that, i think everything that everyone else contributed is right on.

Meaning | Reviewer: Ariel | 11/12/07

I think its about a pair of people that love one another, and the guy can't make up his mind. He wants the girl and he confesses his love but than right after he doesn't act on it. And he says well any other girl would move on, but this girl is hung up she is too in love with this guy to let go. He says that she normally would get the guy, but with him its different its not so simple and she's not going to win. Than he goes on to say that no matter what they just won't work, they don't fit. And its just a circle of emotions. And so they have to move on, because even though they love each other it just never seems to work between them. But in the end this love is the best love either one of them has ever had and they can't explain it.

some more thoughts | Reviewer: linda | 10/28/07

I think many of the aspects mentioned really hit the point with this song. In my opinion, it's about an unhappy relationship between a man (the narrator) and a girl who has had a tough life so far. He has always been trying to understand and comfort her, but she couldn't get over the bad experiences she's apparently had since she was very young - while his life was easy, which is why he maybe can't fully relate to her difficulties ("you've been at the helm since you were just five, while I cannot claim to be more than a passenger"). Still he truly loved her, but that was not enough for the two to really make it together ("you've made it through the direst of streets alright, can you help if plain love now seems less interesting"), especially since she didn't manage to change/get over her past trouble, possibly in the way the two were arguing or discussing things. She might be stubborn in a certain way, insisting on her views and not seeing how he is trying so hard ("You've won one too many fights,
Wearing many hats every time,
But you wont win here tonight"). So finally she's lost him with her destructive behaviour, he can't take it any longer and can't help her to become happy in life ("Let the good times end tonight" and "Just a moment or two from now,
Not a mind will retain even a trace,
Of the thoughts that I struggled to tell
And how our stack of cards just fell,
So settle this once and for all,
The light no longer shows the cracks around my door, And I have no lantern to light your way home tonight"). The "sail her, don't sink her" part could relate to two things - either that he hopes she will be able to eventually have a good and loving relationship (thus sail her-sail love), or then that he hopes she will learn to accept and cope with herself and all the difficulties, hence not sinking herself into depression and trouble anymore.

amazing lyrics | Reviewer: indiechick | 8/22/07

Everyone's theory of the song is really good. But I have my own idea on what the song is about.

It's about a girl who dreams a lot, especially about her future. She doesn't know how to deal with her present life, so she is always dreaming. Anytime she has to deal with confrontation she just runs away. She doesn't know what love is or what it's like to be in love. So she needs to "sink" her fear of the present and "sail" her life and see what happens without running away.

Great tune | Reviewer: Anonymous | 6/8/07

Anonymous I think you've got it, I'll take it one further. She is with a guy who is not good for her, is having an affair with a guy who does truly love her love with her but who she just views as a friend to help her survive her unhappiness. This song is the friend's/lover's plea to her. Wearing many hats everytime = being a friend, lover, acting "proper" with him in public, trying to play too many roles. Wearing all your clothes at the same time = the layers of false self she wears, they protect her but also keep anyone from getting to the "real" her.

what i think | Reviewer: Anonymous | 5/28/07

its about a girl who has so many dreams and is really free spirited and keeps getting hurt by guys that dont really like her and this boy whos loves her but she doesent really recognize him

Many hats | Reviewer: lemongirl | 5/14/07

I think it means: trying to do so many things at the same time...

Amazing | Reviewer: Leah | 3/25/07

This is my favourite song on Wincing the Night Away. I love how he says "Oh girl, sail her don't sink her, this time."

I just don't get the "wearing many hats everytime" and "wearing all your clothes at the same time". I'm not quite sure what that is supposed to mean.

But the lyrics and music together with his (AMAZING) voice is just incredible. Definitely my number one song on this album. <3