Spaw's right. Prine penned songs more numerous than can be easily listed.
The songs that made most sense to me, back then were "Illegal Smile" and "Sam Stone". They were topical in the early 70s. There were a number of other songs dealing with frustration in love (and other emotional baggage) - lines like "..broken bottle; Look's like a wedding ring.." Good luck in your search. I am sure you'll find numerous sources here.