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Keep on clicking to find even more questions to ask when dating! As mentioned above, write the questions on slips of paper and put them in a jar or bowl. Keep in mind: these questions might be too personal to ask a guy on a first date, so save them what questions to ask a guy your dating phone calls after that first date, or on a later date. Thanks for sharing. If you could add one rule that everyone must follow when they use the internet, what would your rule be? If tomorrow was your last day on earth, what would you do in your last 24 hours? What do you feel most grateful for in your life?