Breaking the ice and starting to talk to someone can be very difficult. Someone you've never spoken to before can seem big and scary. Here are some ways of getting people talking that I've figured out.
Be polite
If you want people to like you and want to get to know you, politeness helps a lot. I'm not saying you should suck up to them, but treat them with respect. There's a trend for being rude these days that comes from the movies and TV. It's fun to watch, but that's not how the real world works. When Clint Eastwood is rude and nasty, it's fascinating - when you're rude or nasty, you're just someone who's not worth having anything to do with. Everyone knows what you're supposed to do to be polite - put it into practice and you'll go far with making new friends.
If it's someone you've seen before, say "hello"
It's amazing how many people will be in the same office, same school or on the same bus for years and never speak. Simply say "hi" to a person you see regularly and you'll move from being a stranger towards being a friend.
Practice shy confidence
While shyness and confidence are obviously opposites, you can combine them in opening conversation to great effect. Be confident in forcing yourself to speak to the person in question, but be shy as in letting them know that you respect them enough to worry about their reply. Most people will either try to bowl the other person with their confidence, thus putting them off, or never speak to them in the first place.
The trick is to combine the two approaches. Simply speaking up with a quite "How are you?" will break the ice. Then continue with shy respectful conversation. Most people aren't mean enough to reject a politely shy approach.
Ask questions
This is an old technique, but it works well. As you don't know the person very well, you don't want to pry into anything too personal to begin with. Just keep it friendly and respectful, don't go into interrogation mode. Look for something about them to ask which is likely to receive more than just a yes or no answer - "I like your watch, where did you get it?", "Are you guys busy up there at the moment?", "Do you work in the city?", "Did you watch the tennis last night?".
What you're really looking for is something you have in common that you can leverage a conversation from. Here's an example of a man starting a conversation with a woman at work.
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