Here you’ll find questions you can ask on your first three dates. These are designed to help you learn more about him without asking all the typical questions, and making him feel like it’s a job interview.

Your goal should be to have fun, BE fun, be interesting and interested, and if you’re interested in seeing him again, getting him to want to get to know you better.

Most conversations on the first few dates are typically the same. What do you do for work, what do you do for fun, what movies have you seen, what happened with previous relationships? But what we should really be trying to find out is who this person is in regard to what really matters to them, how good a person they are, how they’ve lived their life, and what their values are.

The following questions are fun, but they’re designed to cause you both to reveal more of your inner selves to each other. They’re separated into first, second and third date questions so that, as you become more interested and more comfortable with each other, you start getting closer to those things that are truly meaningful.

Don’t go on a date with a list of questions, but do select a few you’d like to ask, maybe tuck them into your wallet to refer to. And most important, have fun, assume they’re nervous and do everything you can to make your date feel at ease.

First Date Questions:

  • What is one of the scariest things you’ve ever done?
  • What historical figure would you like to talk to, and what would you say?
  • What do you think people most admire about you?
  • In what ways do you think you’re unique?
  • What are you really good at?
  • What is the most beautiful thing you ever saw?
  • What’s your favorite way to spend time with friends?
  • What kind of artist are you (or would you like to be) and why?
  • In what ways would you like to be more adventurous?
  • What is your favorite place in nature and what do you like to do there?
  • Describe one of the happiest moments of your life.
  • What do you like best about the way you look?
  • What do you like to do when you’re feeling playful?
  • What’s your ideal vacation and why?

Second Date Questions:

  • Of what are you most proud?
  • What are your three favorite things to do?
  • What are your favorite things to spend money on?
  • What three things are you most thankful for?
  • What would you like to do for your work if money was not a consideration?
  • Describe one of your most embarrassing moments.
  • If you had to give away a million dollars, how would you do it?
  • In what ways can a friend count on you?
  • What is a favorite thing you like to do when you have time to yourself?
  • Describe one of your most embarrassing moments.
  • What makes you sad?
  • What is one of the bravest things you’ve ever done?
  • What would you like to learn more about, or learn to do?
  • What was your favorite toy as a child, or your favorite thing to do?

Third Date Questions:

  • What is a secret dream of yours?
  • What would you want to say on national TV?
  • What are you afraid of?
  • What physical trait do you like best about yourself?
  • What would you do if you had only six months to live?
  • What do you like best about your personality?
  • What would be the best way you can imagine celebrating your birthday?
  • If you could go back in time, what would you do over again?
  • What is the craziest thing you’ve ever done?
  • What is the worst thing that happened to you when you were a child?
  • What was the most difficult thing about school?
  • In what ways are you disappointed in yourself?
  • In what ways are you most generous?
  • How would you improve yourself?