Learn About Their Past
Learning about someone’s past can be tricky; you don’t want to seem like you’re giving them the third degree, but at the same time you want to know more about them. By encouraging people to tell stories about themselves, you not only learn about their history but also about them from the way they talk about their lives.
What’s the earliest memory you have?
Where’s the best place you ever went with your parents, and what did you do there?
Tell me about your best friend.
What kind of books (TV shows/movies/video games) do you like? Why?
What’s the worst job you’ve ever had?
What did you enjoy (or hate) about school?
What’s the most embarrassing moment of your life?
Explore Their Personality
These questions are designed to spark the imagination of the person and drift off into speculation. There aren’t really any right or wrong answers; again, the way these questions are answered tell you more about a person than the answers themselves.
Scratching the Surface
If I asked you to cook me dinner, what would you make me?
What’s your favorite thing to do on a beautiful Spring/Summer/Fall/Winter day?
What’s the biggest goal you’re working on now? (Note: be prepared the answer may be “You” and he should get points for quick-witted compliments).
If you won the lottery tomorrow, what would be the first thing you would do with the money?
What do you think is the biggest problem in the world today? What do you think people should do about it?
If you could have lunch with anyone in the world, living or dead, who would you want to meet?
Who’s your favorite movie character? What do you like about him/her?
Some of these questions range from the simple emotional to the blatantly sexual. Not all will be appropriate, but if you are planning to be sexually intimate, they probably are.
Have you ever had your heart broken? What happened?
What was your best lovemaking experience?
What do I need to know about your sex life?
Have you ever cheated on a partner? Why? Did you get caught?
Your Present and Future Together
If you wanted to kiss me where would you take me to make it perfect?
Tell me what you think is the sexiest thing about yourself (bonus question: About me?)
Do you think there is a difference between having sex and making love? What is it?
Make the Questions More Bearable
A few things to remember about these questions:
This is meant to be a guideline, not a list you carry with you and read from. Some questions might not apply or might just inspire other questions. Go with that.
Don’t interrupt perfectly good conversations just to ask the questions. If a guy is happily engaged in talking to you, listen, and learn about him that way.
These questions are great ways to fill in any awkward gaps in conversation.
Remember, you want to avoid “yes/no” or single answer questions. “Where were you born?” has one answer; “Tell me about your childhood?” can lead to many conversation topics.
Make It a Game
You don’t want your date to feel like an interrogation or a job interview, so you’ll have to take special precautions to make the question and answer process more bearable. You could each write down questions on scraps of paper–serious and fun so the mood doesn’t get too heavy – and throw them into jars (yours in one, his in another). Take turns fishing out questions and answering them. You could also play a game where, for every point scored, the person who earned the point gets to ask a question. Just be sure to choose a game you’re sure to win or tie, or you may find yourself doing all the talking.
Keep It Natural
Unless you’ve both decided to have a formal session of getting to know each other by asking any questions that have been on your mind, keep things low-key. Let the questions follow each other naturally as the conversation unfolds. Ask one of the lighter questions and follow that path until you get to a point where you can ask more serious ones. Don’t sit down at a restaurant on a first date, order your drinks, and immediately launch into rapid-fire questioning or there may not be a second date (what a total disappointment if you liked their answers!). Once you both know you’re interested in learning a lot more about one another, consider the more structured “Twenty Questions” type of conversation, whether you’re just talking or including it as part of a game.