Others remind me of people I dated - one of my high school girlfriends and I listened to Bjork's Post and Morcheeba a lot. A later girlfriend introduced me to Kirsty MacColl.
I also associate albums with where I purchased them, either because they're clumped together (I bought a lot of albums at a Manhattan Tower Records in ninth grade, including Bee Thousand, Be Bop Deluxe's Sunburst Finish; in eleventh grade, I remember buying Pink Flag and Marquee Moon among others at a Kim's Video And Music) or because I got them on vacation.
As far as specific moments: I think my first kiss/makeout may have been to a Drifters compilation. I think my second or third was to the Live/Dead version of "Dark Star", which had come up on my Winamp on shuffle - I remember being terrified that whatever came up next would completely kill the mood, but fortunately it didn't.
When I got my first post-college job, I splurged on some albums at a Virgin Megastore - I think they were Peter Bjorn & John (mostly boring), the Vashti Bunyan comeback album (nice enough but I never listen to it), and I think a couple others (maybe The Only Ones?) that weren't especially good either.