This song is about someone who is very timid in telling their significant other how they really feel. Instead of expressing their discourse for the relationship, they "settle" for what they have and wonder about what might have been.
In an interview with the Rock and Roll Hall of Fame, Ben Gibbard explained that when he wrote this song, he did not like it. He brought it to the band expecting it to get discarded, but guitarist Chris Walla demanded it go on the album. A good decision, as it has since become one of their more popular singles.
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