This was not hard for me at all. There are bunches of songs that I have just gotten totally sick of over the years, but honestly, the first one that came to mind stuck.
I had to pick, “I Will Possess Your Heart” by Death Cab for Cutie. I am not going to go into my reasoning for my loathing for this song. I will just say the reason is a specific person (who lurks around here from time to time, against my polite request that he stop). This person is not a bad person. Not a serial killer (I hope) or anything like that. Just someone I am reminded of when I hear this song and someone I would rather not have to be reminded of at all. And it sort of ruins the whole thing for me. All 35 minutes of it.
(And no lie, iPod is on shuffle and guess what song just came on!)
Note to self: Update iPod. Stat!