Dear John

I love the boxing imagery.

"Throwing kisses so Richmond's unfortunates can go on"

Light hits so that the poor slobs fighting John don't end up in intensive care.

A song recalling the beginning of a relationship uses a title which predicts its ending. - "Dear John" letters were the most frequent fore-runners of suicide for men in combat in fiction. They must be devastating IRL too.

"Numbers come up" suggests he is dead and the Kuala Lumpur reference refers to the uncertainty.

I think that "number's come up" means that John was drafted, and sent to Kuala Lumpur, and Caroline at some point tries to contact him, but "somebody stationed" there says "he thought you went out" meaning that John is probably out cavorting with local women, or at least that's what Caroline is probably thinking at this point.

Have a look at the Wikipedia description of a Dear John Letter: http://en.wikipedia.org/wiki/Dear_John_Letter

It seems to me that this song is simply a Dear John letter, done Aimee Mann style.

The song begins with the beginning of a relationship, when Caroline (the narrator, whose name isn't given in the song but which we know from the rest of the album) sees John boxing at the fair in Richmond, Virginia. But there's a big leap in time and events halfway though, with "But numbers come up". So at some point John was drafted and in Kuala Lumpur (!), and Caroline is singing this from some time far in the future with respect to the beginning of the song. Now the midway itself is gone and it would seem that the memory of John himself is fading. So the song brackets the beginning and the epilogue of a relationship. But what happened? How did John get drafted, how did they lose touch? The song doesn't tell us.

What is left is a memory of a memory, and a pervasive melancholy.