Pity and Irony

This section of the story confused me. They seemed to ramble on about a topic that makes no sense to me; come to think of it, Bill doesn't make a lot of sense most the time! On page 118, Bill presents the words pity and irony to Jake: "'Aren't you going to show a little irony and pity?' I thumbed my nose. 'That's not irony.'" For some reason, this was one of the most confusing parts of the story for me! I'm not sure if I was just thinking too far into it, but what is Bill talking about!? Bill then describes the words as the name of a band that's popular in New York. He tells Jake to ask the girl for jam in an ironical way, and when Jake fails to do so, Bill says, "That's not ironical. I wish I could talk Spanish." There must be something about the way Bill wanted Jake to talk to the girl so that his question could have been taken two different ways.
On the other end of the spectrum, maybe Bill is hinting at the irony and pity Jake tends to carry around in his life because of Brett. Irony that they both love each other, yet she's with other men; pity because it's a shame Jake can't get the girl.