I'm going to go with "Out of My League" by Stephen Speaks.
This reminds me of my dear Kaylie Hancock now Sikahema.
We were sophomores in high school, and Lj had sent this song to Kaylie, and said it was the song that described her... Or made him think of her... Or something equally cute like that. Kaylie and I thought it was the cutest thing ever. We fell in love with the song (more so Kaylie, I'm sure) and one night we had a sleepover, and fell asleep to that song, each one of us with one ear bud from Kaylie's iPod in our ear.
That's exactly what it makes me think of.
... and maybe it secondly reminds me of Mr. Rich, my junior English teacher, because he played it for us in class in our music analysis unit, and analyzed it to death. But that's another story.
(sorry the quality is not awesome - it's the best youtube could do)