Lyric discussion by sukireru 

Cover art for Walking By lyrics by Something Corporate

Well, I already said what I thought the 'Cheshire Cat Doorstop' was referring to...the girl who's leaving him. I can just picture her, standing at the door (she's about to leave, holding the door open, as a doorstop would), smiling because she wants him to not be sad, to smile back, too, because it hurts her, too, to be leaving him ((the Cheshire Cat in Alice in Wonderland was known for smiling, as shown best in the Disney adaptation, when he disappears completely except for his smile))...like when you know that things aren't ok, but you smile sadly anyway because you want everyone else to be okay...the girl is always smiling, though she is crying because it hurts her to go.