'Drop a caribou' means that the protagonist is suggesting that he might put a Canadian quarter into a payphone and tell on his ex.
Overall, the song is basically the ramblings of a man who is speaking to a former lover with a lot of bitterness but also a kind of awe. It's like he has just lost all the vestiges of affection that he had for her and he is hyper-conscious of this. I always picture him saying all of this out loud in an empty room. He knows that nothing positive can come out of saying these things to her but he has to say them out loud to move on.
'Drop a caribou' means that the protagonist is suggesting that he might put a Canadian quarter into a payphone and tell on his ex.
Overall, the song is basically the ramblings of a man who is speaking to a former lover with a lot of bitterness but also a kind of awe. It's like he has just lost all the vestiges of affection that he had for her and he is hyper-conscious of this. I always picture him saying all of this out loud in an empty room. He knows that nothing positive can come out of saying these things to her but he has to say them out loud to move on.