If tomorrow you woke up with a new quality, talent or ability, what would you like it to be? If your house caught on fire, what would be one thing you would have to save first? What’s your most terrible memory that you’d love to forget about? If you could have dinner with anyone in the world, past or present, who would it be?
If you could play the role in any movie, what person would you want to be?
What’s one thing you’ve learned that most people don’t know how to do? How do you spend your free time, and where do you like to go? What is one habit you’re the most proud of breaking? What is one thing you were afraid to do, but felt amazing after you accomplished it?
The examples below are intended to stimulate your own ideas rather than as rules. Why: Is the person about to make any major life changes e.g., leave their $200K/year job to go back to school? Do they see it as a job, a vocation, or are they primarily motivated by climbing the career ladder?
Key goals of a first date are to (a) see if you have a connection, and (b) find out if you and your date have any major areas of incompatibility. Why: Does the person have strong feelings or are they more easygoing and with milder feelings.
What or things or person has influenced you the most?
If you were able to see in the future, what would you tell yourself or want to know?
Just remember one thing: Why waste time when we have so little time on the planet to be us.
When scientific dating facts have shown asking big, risky questions gets a more positive response, what’s to lose? How does love and affection play a role in your life? What’s one thing you’ve done, but will never end up doing again? They will put both you and your date into a vulnerable position, and force you to go to an internal place and ask why? Instead of saying things to be more attractive, or perhaps fool yourself self into liking her more, it allows both of you to be authentic and real. Also, if anything out of the ordinary has happened that might be affecting your date’s mood, it’s good to factor this in. Also, it’s nice to give your date an opportunity to answer a question that isn't directly about them. On a first date go for a friendly tone rather than an intimate tone when asking this question. Don’t be afraid to change plans if you arrive at a restaurant and find it’s too noisy for a good conversation. If you had unlimited money, what would you do with it? What are the craziest things you’ve ever done with someone else?