Once you've mastered that, ask them to pretend like they are a stranger so you can approach them and open a conversation 20 times in a row.

A friend actually did this exercise with me when I was about grade 9. At the time I was not so much shy as overwhelmed by small talk; I couldn't process it in real time, so if someone said "what's up?" to me I would freeze and eventually blurt out some rude-sounding conversation-killer. We were on some kind of volunteer field trip, I think, and we spent an hour in the hotel room with her 'starting conversations' with me and me responding. ...Wow, I had actually forgotten I had that much trouble with social skills.

Answering questions like this 100 times in a row will reveal how often most of us speak softly, fail to enunciate, and use filler words like "um."

Some of us wish we could learn to speak more quietly! I don't know if it's because of my family dynamics or the crowd I hung out with in high school, but when I'm excited I speak very loudly and people find it disruptive.