Break the Silence The Art of Conversation. Ask Question to Initiate Conversation The art of conversation is more about what you get others to say than what you contribute to the conversation. People love to talk about themselves, and if you have some fun questions to ask in different situations, you’ll be the person known for keeping interesting conversations going in any situation. If you’re sometimes uncomfortable in certain situations a few interesting questions can become real ice breakers. You’ll soon be involved in an interesting conversation and you’ll learn a lot about the people you’re talking to. Sometimes you are in a group of people at a party where you don’t know anyone, or you may be sitting with someone waiting for a bus. There are plenty of situations where you may strike up a conversation to pass the time, but aren’t sure what to talk about. Talking to strangers can be one of the hardest things to do, if you’re introverted or unsure of yourself. Thinking of a decent ice-breaker that might interest a stranger, but not appear to be a come-on, is hard to do when you’re sitting on a bus or in the waiting room at some office.