21 Questions to Ask a Guy When Dating

Updated June 2, 2022
Happy couple having coffee while sitting at cafe

Dating is like an intricate dance. You learn about him, and he learns about you. There are hundreds of important questions to ask a guy when dating, but keep in mind that you can't ask them all at once. It's helpful if you can find the right combination of fun and serious questions, especially during the first few dates; the last thing you want is for the conversation to feel like a test.

Discover more about someone you're dating with conversations that help you really connect. You can explore his past, present, future, and personality as long as you know which questions to ask. Whether you're meeting up in person or you need a set of online dating questions to ask him, the following 21 questions to ask a guy are sure to help you better understand the person you're dating.

Revealing Questions to Ask a Guy

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. These are meaningful questions to ask a guy before dating gets too serious:

1. What's the earliest memory you have?

2. Where's the best place you ever went with your parents, and what did you do there?

3. Tell me about your best friend.

4. What kind of books (TV shows/movies/video games) do you like? Why?

5. What's the worst job you've ever had?

6. What did you enjoy (or hate) about school?

Questions to Ask a Boy About His Personality

These fun relationship questions are designed to spark the imagination of the guy you're dating. There aren't any right or wrong answers; the way these questions are answered will tell you more about him than the answers themselves. Here are some good questions to ask a guy when dating to learn more about his personality:

Couple on a date at the park

7. If I asked you to cook me dinner, what would you make me?

8. What's your favorite thing to do on a beautiful Spring/Summer/Fall/Winter day?

9. 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).

10. If you won the lottery tomorrow, what would be the first thing you would do with the money?

Serious questions to ask a guy to explore his personality include:

11. What do you think is the biggest problem in the world today? What do you think people should do about it?

12. If you could have lunch with anyone in the world, living or dead, who would you want to meet?

13. Who's your favorite movie character? What do you like about him/her?

Deep Questions to Ask a Guy

Some of these 21 questions to ask a guy will help you explore his feelings and romantic side. If you are considering becoming more serious in the future, these are important questions to ask a guy when dating. Before you take your relationship further, knowing a guy on a deeper level is essential.

14. Have you ever had your heart broken? What happened?

15. What was your best relationship?

16. What do I need to know about your previous partners?

17. Have you ever cheated on a partner? Why? Did you get caught?

18. If you wanted to kiss me, where would you take me to make it perfect?

19. Tell me what you think is the sexiest thing about yourself (bonus question: About me?)

20. Do you think there is a difference between having sex and making love? What is it?

21. How do you think aging will affect your attraction to me?

These revealing questions to ask a guy should elicit more questions from you and shouldn't merely be a quick checklist of questions. Ask for elaboration when appropriate and if your guy is particularly brief when answering a question, you may want to ask some follow-up questions to get more details. Either way, these 21 questions should provide you with plenty of things to talk about with your boyfriend.

How to Ask Good Questions

Here are a few things to remember about these questions to ask someone you're dating:

Make the Questions More Bearable
  • Don't ask questions via text that you expect to get lengthy responses to. Some questions are fine for quick text conversations, but more in-depth questions should be saved for face-to-face conversations or over the phone.
  • This list of 21 questions to ask a guy when dating is meant to be a guideline, not something you carry with you and read from. Some questions might not apply or might just inspire other questions. Go with that or use them as conversation starters.
  • 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 good ways to fill in any awkward gaps in conversation, and many are great online dating questions to ask him.
  • Remember, you want to avoid "yes/no" or single answer questions to ask someone. "Where were you born?" has one answer; "Tell me about your childhood?" can lead to many conversation topics with a guy.

Make It a Game

You don't want your date to feel like he's being interrogated or at 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 21 questions on scraps of paper and throw them into jars (yours in one, his in another). Take turns fishing out dating questions and answering them.

You could also play a game where for every question answered you get a point, and the person who earned the point gets to ask the next question. If someone doesn't answer a question, they don't get the point. 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 having a more structured conversation, whether you're just talking or including it as part of a game.

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21 Questions to Ask a Guy When Dating