I once owned a really really ugly pair of white leather boots. They were so bad. It was back in the '80s! It was just a really tacky fashion choice when I was in middle school and I thought it was cool. I'm really embarrassed.
I heard the Beatles and the Stones and Mom bought me an electric guitar. I played lead for four years and then switched to bass. One day someone suggested that I should sing so I sheepishly stepped up to the microphone and the rest is rock history.
