Lyric discussion by InPerfectRuin 

Cover art for The Jeopardy of Contentment lyrics by What Made Milwaukee Famous

I agree with PinsNeedles, however I feel there's more to it than that. The title says it all: the Jeopardy of Contentment. The song is about that period in a relationship after everything becomes too comfortable. To me, it's about what's at stake when a relationship reaches that point, when the flame is gone and we settle for contentment instead of true happiness. Indeed, the lyrics describe a relationship where the partners no longer relate, where they've been through a lot together but the relationship just isn't what it used to be: "In our destroyed machine". The narrator (for lack of a better term) here still loves their partner but feels that the relationship just isn't strong enough anymore to last. They want something better for their partner and decide to make the sacrifice of ending the relationship in hopes that the other person will find what's best for them "there's got to be something better out there, someone better out there for you than me". Its about giving up before there's any more damage.