Fellow shy individual here, this is what I've learned through the years to break out of my shell in terms of conversations. Develop your listening skills, and be sure to ask questions about others when you are out in public. Sincere compliments can go a long way to break the ice- then engage in conversation regarding common interests you may have, what people do for a living, latest books/movies people have been checking out, etc.
If you focus on letting others talk about themselves, there will be opportunities to reciprocate as others will want to get to know you. Go to places where you feel comfortable with the interest and environment and that should take some of the pressure off in terms of making a conversation flow. For instance, I love going to live music shows and bowling- so either situation makes me less nervous and more open to discovering new people.
Please feel free to keep us posted on your progress.
Matt
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