Practice. Set a goal of "this week I'll start a conversation with X strangers". Each week increase X a bit. It's like an exercise routine: start slowly and gradually up the weights and repetitions.
Some tips: store lines are good. Most people are bored and happy to talk to someone for a diversion. And if you do bomb horribly, chances are you'll never see them again. If you're in a fast-food places, say to the person next to you "Say, I usually get the same thing each time. I'm looking to mix it up, what are you getting?" Clothing store? "Hey, those clothes look nice. You have good taste!" Convenience store, person has beer and snacks? "Hee, looks like you're on your way to a party!" DVD rental? "Oh, that movie looks good, what’s that about?" You get the idea.
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