Lyric discussion by preciousbane 

Cover art for Caldecott Tunnel lyrics by Something Corporate

Caldecott Tunnel is in CA, in Berkeley Hills. I spent so long thinking that this was about the fire in third bore, when they closed that and the adjacent bore, but... it can't be. I'm pretty sure it's about two girls, one who he isn't necessarily with, but who wants to be with him, and doesn't know he's with the other girl. So he needs to let her know, but gently, because he doesn't want to hurt her. I know that really, the only person who can say is Andrew McMahon, but until then...I'm happy with that interpretation, I think.

My Interpretation