Dave Matthews explained this song to Relix magazine: "It's a goodbye song. It's a heartbreaker. That's a hard one for me to listen to. I love the strings that Dave Campbell arranged. When we first played it, we had a whole band arrangement, and it was pretty loud. But when I wrote the lyrics, the song said, 'I'm not loud! I'm just big chords. Play me quietly and then I'll make sense.' The interesting thing about lyrics sometimes: they can be really demanding. If I didn't feel so strongly about those lyrics, I probably would have turned to some other lyrics that fit with the heavier groove. But those lyrics they landed right where I wanted them. So then I said, 'What do I have to do to make these lyrics land?' And so that meant just play the guitar."
The band's sax player, LeRoi Moore, tragically passed away in the summer of 2008 as a result of an accident on his farm. Matthews told Relix about his contribution to this song: "Roi really liked that one. His musical instincts were like no one else's that I'd ever met in my life, and with that song, Roi said, 'Man, that's a big song—don't make it too big.' And he was right, because in the end, I took everything off and just had the little guitar."
The album was produced by Rob Cavallo (Green Day, My Chemical Romance) He told Relix about his use of a string section: "There are three songs that have a mini-orchestra on them: 'Dive In' 'Squirm,' and this lovely, touching ballad. With the size and scope of this album, I thought I'd use a larger string section than I normally do with a rock band. We ended up using 30 pieces—18 violins, four violas, six cellos, and two double-bass—and that's quite a larger size. Usually you hear of something more like 20 pieces in rock. It's on the larger end of the scale before it turns into a symphony—which you wouldn't want."