Instead, I spent way, way too long narrowing everything down. LIke pobig, I restricted myself to one song per artist (I ended up with one exception). Also, I recently made a pair of mix CDs and I've been meaning to post the songlists here, so I intentionally avoided naming any songs from that (except one).
One of my ex-friends is also what canetoad once called a "neverlove", a term which has stuck with me and that I always use mentally now. I originally had slotted her (the neverlove) for the ex-friend question, since as a neverlove she wasn't an ex-lover etc., and there was no neverlove slot. (Although 'reminds you of the one you want' is close, but it's no longer current). I associate lots of music with her--she was a fan of Yes and Genesis (mainly because she had the hots for Jon Anderson and Phil Collins, but you take overlap where you can get it), and I also associate the music from Final Fantasy II with her, since we played it together. But although there are entire albums that made me think of her, I spent the time really pushing it--I would grab two questions at a time and skim through all 300 of my CDs, looking for associations--and finally latched onto the really crucial ones--although I never heard See the Constellation until after I stopped talking to her, she and I used to hang out on top of a building next to her apartment and watch the stars. We saw quite a few shooting ones, too, even though they weren't special meteor shower days. It's also a song about loss, so at some point, back when I heard it after we had split up, I started associating it with her, and now that association is fairly unbreakable. If I think of her, I don't think of the song; but if I think of the song, I think of her. So it took a fair amount of effort to track it down.
And the thing is, as I went through Cure for Pain looking for just the right song that evokes sex, I realized that these tracks and their smoky bass-heaviness used to make me think of sex, but they didn't anymore. Instead, they made me think of a lover I had shared Cure for Pain with, for whom, when we broke up, that album then left her with painful associations. And knowing that fact, it rubbed off on me, in a way. I now associate that album with her being hurt, with the breakup. So then it was a simple matter of picking the "right" song--not that that song makes me think of that event any more than the other songs on the album, but because the song is connected in lyrics and mood to the idea--and is one of my favorite songs from the disc anyway.
But working all this out took a lot of effort--breaking past the obvious associations and digging deep into my real reactions. Of course, in places, I did some obvious ones: "makes you think of love -> If I Think of Love" for instance. But even those tend to hide subtler things; I had originally put that song in a different place, and decided that the title correspondence was too close, and I had to use it. But in the meantime it opened up the possibility of something else for "reminds you of the one you want", and forced me to hunt through my CD collection again. I don't think I've even heard the song I picked since the time I started wanting the person I currently want, but the moment I spotted that CD and remembered that song, I instantly connected it, and it really is strongly linked in my head now. So in return for getting the apparently simple naive "love" response--which isn't really quite as naive as it seems anyway--I got a very dark, very self-criticial comment on my current crush--a self-criticism I've been aware of and cautious about but never had stated so bluntly before connecting that song to it.