If confidence is something you struggle with, then the suggestion of striking up a conversation with a stranger is probably about as appealing as getting hit by a bus. Here's your chance to face your fears in a low-risk setting, and when you get past the first few awkward encounters you'll find that approaching strangers, or anyone at all really, gets easier and easier. Remember, there's nothing at stake with a stranger. If it goes horribly, you never have to talk to that person again, but you will have still seen what didn't work about the interaction. On the other hand, if it goes well, anything can happen. A new business contact, a date or even just a pleasant exchange can make you feel like a rock star.