Good and Thoughtful Questions to Ask a Guy on a First Date

In this website we talk a lot about how crucial a first date is, for a future relationship. You should be ready for this day and get rid of your shyness.

Talking face to face with the guy you like, will never be easy. But don’t worry about it. Knowing what to ask and what to answer is the key to a successful first date and to unveil his personality.

You can practice about it at home first. Think of the topics you want to talk about, in order to understand more about him. Don’t forget that you should also be ready to answer these questions asked by your partner.

In this post you can find many good and thoughtful questions to ask a guy on a first date.

General Questions

Usually on a first date, there will be exchanging questions between both parties in order to know each other well. At first you can ask some general questions about his hobbies, family and something light about him. Remember not to ask something that is too serious and heavy if you don’t want to scare him away.

Just consider these simple questions as an “appetizer” to melt the tense between you two. So let’s check them out.

  1. How will you describe a healthy relationship?
  2. What do you think happiness is?
  3. What did you think of me the first time you saw me?
  4. How many brothers and sisters do you have?
  5. Do you still live with your parents?
  6. How much influence does your family bring to your life?
  7. Do you have a pet?
  8. What is your favorite color?
  9. What do your parents do?
  10. How do you see friendship between male and female?
  11. How do you see love? Is it a priority in your life?
  12. What is your favorite movie, TV show or book and why?
  13. What kind of music do you listen to?
  14. Have you been to a concert?
  15. What do you for living? Do you like your job?
  16. How many hours do you work a week?
  17. How do you refresh yourself after being tired from work?
  18. Are you happy with your life?
  19. Which one do you prefer, a good restaurant or a night club? Why?
  20. What are your hobbies and how often do you do them?
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Questions about his past

After asking something light, you can later ask some questions related to his past. His past says a lot about his personality and his habits. Don’t ask something that is too private. Limit yourself before you make him get annoyed by your questions.

The most important thing is NEVER judge him for his past. Try the questions below and you will manage to retrieve many interesting things.

  1. What was the happiest moment in your life?
  2. What was the most embarrassing moment in your life?
  3. What is the best place you’ve ever been for holidays and what did you like most about it?
  4. What is the thing that you regret doing the most? If you had a chance to change it, would you do it?
  5. Why did you break up with your ex-girlfriend?
  6. What mistakes did you and your ex do in the past, that you don’t want them to happen again in your next relationship?
  7. Have you ever been betrayed by your best friend?
  8. Has somebody ever disappointed you so much that you find it difficult to accept till now?
  9. How was life when you were a child?
  10. Where did you live as a child?
  11. How did you see love and marriage in the past?
  12. Have you ever had any troubles with your colleagues or your boss? How did you solve it?
  13. Why did you choose to work as……?
  14. Before working here, where did you work? Why did you move?
  15. How was your school life?
  16. What kind of club did you join during your school days?
  17. Have you ever had a crush on your teacher as a child?
  18. What was your best and worst experience during your school days?
  19. Were there any traumatic experiences in the past? How did you deal with it?
  20. Have you ever been overseas before?

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Questions about his personality

Step by step you can now ask some questions in order to know more about his personality. Although it’s not possible to get complete understanding about what kind of person he is, at least you can know whether there is a possibility for the relationship to continue and grow.

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You surely don’t want to fall for a selfish and irresponsible guy right? But please remember to be careful with your questions and don’t push him too much for an answer, or else they will bring you the opposite results. Below are some ideas of questions to ask him.

  1. Do you enjoy meeting new people?
  2. How do you feel to be in the middle of a crowd?
  3. Which do you prefer, buying new things or repairing the old ones?
  4. How do you take responsibility for your mistakes?
  5. Do you always consider other people’s feelings before deciding something?
  6. Will you describe yourself as an open minded person?
  7. How do you react to changes?
  8. Do you think that a mistake gets you closer to success?
  9. What will you do to avoid doing the same mistakes?
  10. How do you feel if there is someone criticizing you?
  11. What is your reaction when you can’t get what you want?
  12. Do you talk about your problems or do you keep it to yourself?
  13. Are there any moments that you prefer telling an easy lie to the hard truth?
  14. In situations that you and your partner feel disconnected, what will you do to get back together?
  15. Do you trust people easily and are you trustworthy?
  16. Can simple things bring you joy?
  17. What can make you smile and bring you happiness?
  18. How would you react if a friend of yours told you that your girlfriend was cheating on you?
  19. Have you ever been jealous to your ex-girlfriend?
  20. What makes you think that someone deserves a help?

Questions about his future

It may sound a bit weird to ask questions related to a guy’s future on a first date! It’s because future is not something that you can make sure of. It’s true, but it’s something that you can predict by looking at the actions and planning done in the present time.

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Asking questions about his future plans doesn’t mean that you are already sure to get married to him. The point is that you can have a clear view of your possible relationship. Why wasting time on a guy that doesn’t even care about his future? So let’s see what kind of future related questions you can ask him:

  1. How do you see yourself 10 years from now?
  2. What is your next goal for the near future?
  3. Have you done every single step that is needed to achieve your goal in the near future?
  4. What is your opinion about family and kids? Can you imagine yourself as a parent?
  5. What is the next place you want and plan to travel?
  6. What is the next product you plan to buy?
  7. What’s something you’ve always wanted to try and are planning to try in the future?
  8. What would you do to grant your wife and kids happiness?
  9. What is your long term goal?
  10. How important is a marriage for you?
  11. How do you see your job now? Are you satisfied with it?
  12. Do you have something that you want to accomplish?
  13. Will you allow your wife to work?
  14. How do you want your kids to be raised?
  15. What is your next plan for your business?
  16. What criteria will you look from a girl to make her a good suitor for you?
  17. How will you pay gratitude to your parents that have raised you?
  18. Have you ever considered joining your siblings for a business?
  19. What is your dream wedding like?
  20. Which one is your priority after getting married, your family or your job?

In conclusion, going on a first date can give you insight about the guy you are dating through the questions you ask. But you need to keep in mind that the questions we give you here are just guidance so that you can consider whether or not to continue the relationship.

We don’t guarantee you anything with them. So good luck with your first date then.

Thoughtful questions to ask a guy on a first date

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