Ok, lots of songs but the first was Bruce Springsteen's "The River". It's a song of an unplanned pregnancy and lost dreams, how life sometimes takes us places we never thought we'd go.
The following are listed by performer, not necessarily Julie Miller--"Broken Things". This is a religious song, so if you aren't, you probably won't like it.
Richard Shindell--"Wisteria" I don't know for sure if this song is about what I think it about, but to me it's about a man whose wife has died, and he is remembering their life together.
Springsteen again (what can I say, my formative years were spent in New Jersey) with "41 Shots". It makes me angry and wistful and so very sad.
There are too many others, music can touch me in ways that my WASP upbringing won't otherwise allow!
And I kinda have to agree with mousethief on his selection ;-)