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However, with a little preparation, you can carry on a first-date conversation with ease and grace. Here are a few tips for the first date as well as starter questions that will help you get to know each other better. Relax: You want to gain some insight, but you should also remember to have fun. Make sure to ask some fun questions. Being overly suspicious and defensive will likely be off-putting to your date. If you like to argue, join a debate club.