If you and your date are starting to hit it off, it’s time to start slipping in some slightly more personal questions, while making sure neither of you feel compelled to reveal too much. If you could only eat one thing for the rest of your life, what would it be? If you won the lottery tomorrow, what’s the first thing you’d buy?
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? 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? Time to seal the deal—the last few minutes of a date are crucial to make sure a second date happen. Do you have any fun plans for the rest of the weekend?