Reluctant Heart-Breaker

A friend from work just broke up with a guy she's been with for six months. She knew from the beginning that he was not a forever boy. He was sweet and cute and treated her spectacularly well, but he didn't have the edge she wanted. When he first said he loved her she experienced a crisis of conscience, but let it go with the hope that she would eventually "love" him, as well. She didn't, so needless to say, this break-up was in the works for a long time. Despite all her mental preparations, when she actually pulled the trigger she was a mess for a few days. I knew how she felt. It wasn't the fact of being alone, or concern over actually missing him; it was the feeling that she had done a bad thing to a good person. It was the lingering sadness from knowing that he truly did love her (as naive as that love may have been) and that she had broken his heart.

I say all this only to introduce my favorite ballads of the reluctant heart-breaker. I started this list with the intention of burning an olde-fashioned "Mix CD" for this woebegone friend, but by the time I had gathered even a smattering of songs, her woe was actually gone. So I put it to the viewing public: what classics am I missing?

Dar Williams - February



James - Tomorrow



Fiona Apple - Carrion


(Her intro here is a bit much, but accurately illustrates the point, I guess.)

Bob Dylan - Don't Think Twice It's Alright



Ai DiFranco - Sorry I Am



I've included Jeff Buckley, Bjork, and Death Cab for Cutie, in addition to the album versions of the songs above on this mix: