No worries; you don’t need to remember all of them! You can also use one of these questions in your email correspondence. What have other people you've dated liked the most about you? What have other people you've dated complained about the most? Have you ever struggled with any mental health issues? How do you honestly feel about dating someone who has mental health issues of their own? Why did you break up with your last significant other? Why did your last significant other break up with you? If I ever meet your parents, are they going to be nice to me? Are you dating because you want to find love or because you're just afraid of being alone? If you could change anything about your personality, what would it be? Are you going to pay for this date, or should I have my wallet ready? Are you just going to sleep with me and never call me again?