I do this all the time. I also attach it to that point of my life, and when I hear it again I feel like I'm back in time. All the feelings come rushing back. It's addicting to listen to songs that have a deeper meaning for me.
My father once played his favourite song "Good Time Charlie's Got The Blues" approximately 35 times on our living room stereo. He wanted to memorise it. When he was done doing that he said to my mother, who had been sitting there reading the newspaper, "so do you like my song?" and my mother said "not anymore".