xkcd has some brilliant writing, although some of it has a bit of a comp-sci nerd/programmer in-joke feel to it. Still, it really appeals to both the overt nerd and the closet romantic in me.
And yes, I don't doubt that the author has more than a little relationship baggage. He really does express it well though, despite (or perhaps thanks to) the very simple artwork.
Ah, I loves webcomics.