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Just like the difficulty of starting up a conversation, keeping it going can be equally as challenging. One of the best ways to break the ice is to bring a little humor to the table from the jump. However, there is such a thing as trying to be funny and coming off too corny, which can kill the mood quicker than a ray of light. It is important to judge the situation and start off slow, maybe with a few jokes or conversation starters. In fact, one of the best ways to start a conversation with a stranger, or with someone you would like to get to know, is by asking them a few humorous questions to get them in the spirit of harmless conversation, Once you get them opened up, you might be delighted or at least surprised at what you may find out.