Lyric discussion by isaywho 

I think the song is about a guy who has been with a girl for a long time but is feeling like he doesn't want to stay with her any more. He's "paid all his dues" by doing everything he was supposed to but he doesn't feel like he should stay any longer.

The problem is that he's really comfortable with the girl since "she knows him so well" and he doesn't exactly know how to leave so he stays anyway because it's easier for him to act like it's okay between them than to be honest about wanting to leave as he says in the line:

"It's harder to leave with my heart on my sleeve than to stay and just pretend"

The girl either recognizes that he wants to leave and prevents him from doing so or she just needs him to stay so badly that he is unable to gather the nerve to leave her. Either way, she knows that he won't leave her if she asks him to stay as is described in the lines:

"And like the back of her hand she already understands everything 'Won't you stay?' she says And she already knows how it goes and where she stands I'll stay anyway"

Basically, it's a bittersweet song about wanting to break up, but not quite being sure how to do it.

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