288 Questions To Ask A Guy To Get To Know Him Deeper

Figuring out how to get to a guy can be a bit difficult. The last thing you want to do is say the wrong thing. This compilation of good questions will help you get to know him deeper while avoiding feeling awkward when talking to him. They will also help you lay a foundation for a strong personal and intimate relationship.

Scroll through the different sections, and you will find interesting questions suitable for all circumstances. This list has questions ranging from deep and personal to funny and flirty.

Sections

  1. Flirty
  2. Over text
  3. To know his intentions
  4. Serious
  5. Random
  6. Funny
  7. If you just met
  8. Before dating
  9. Before a relationship
  10. On a date

Flirty questions to ask a guy to get to know him deeper

Are you trying to figure out the best way to know a guy’s flirty side? Well, we’ve got you covered. Answers to these seemingly dirty questions will help you know everything you need to know.

1. What do you think of every time you close your eyes?
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2. Do you ever think about me when we are not talking? What do you think about?
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3. What is the first thing that comes into your head when you think about me?

4. What’s your biggest turn-off?
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5. If I was a flower, what kind of flower would I be and why?
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6. What would you do if I kissed you right now?

7. What is your favorite pet name for a girlfriend?
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8. What’s your biggest turn-on?
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9. What is the hottest memory you have of us?

10. What’s one thing you would like to try with me?
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11. What physical features do you find most attractive about me?
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12. Are you willing to try new things?

13. What color do you think would look best on me?
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14. Describe your idea of a perfect night at home?
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15. What do you think is on my mind right now?

16. Do you like it when the other person makes the first move?
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17. What is the worst/best date you’ve ever been on?
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18. Who is your celebrity crush?

19. What is your favorite thing about me?
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20. Are you good at giving massages?
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21. What is the first thing you noticed about me?

22. Which qualities do you consider attractive?
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23. Am I your type?
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24. Big spoon or little spoon?

Questions to ask a guy to get to know him deeper over text

Avoid flooding your chats with boring and basic questions by sprinkling these deep and thought-provoking questions into the conversation.

1. If past lives are real, what is yours?
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2. If I asked you at 5 years old what you wanted to be, what would you say?
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3. Have you ever seen something you cannot explain?

4. What is the strangest dream you’ve ever had?
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5. What is the darkest thought you’ve ever had?
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6. What would you consider to be your three deepest fears?

7. What do you spend most of your day doing?
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8. Do you have a daily or nighttime routine?
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9. What makes you feel uneasy or anxious?

10. Would you consider yourself a shy person?
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11. Do you have a favorite book?
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12. Do you remember a time in your life you felt most alive? Tell me about it.

13. Have you ever done anything illegal?
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14. Tell me about a time someone broke your heart?
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15. Are you a heartbreaker?

16. What has been the most vulnerable moment of your life?
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17. What do you think about makeup?
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18. What do you think about online dating?

19. Have you ever been catfished?
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20. What are your three top priorities?
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21. Where do you see yourself in the next 5 years?

22. Would you like to get married?
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23. How many children would you like to have?
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24. Do you have a close relationship with your family?

25. Who do you value the most between family and friends?
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26. What is your most prized possession?
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27. When was the last time you cried?

28. What is your worst habit?
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29. Do you believe in second chances?
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30. Do you believe in fate?

Questions to ask a guy to know his intentions

Sometimes you just don’t know what the other person wants. This is a list of good questions that will help you know his intentions. This way, both of you move at the same pace and in the same direction. You really do not want to be head over heels for someone who is considering you as a friend at most.

1. Where do you stand regarding commitment?
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2. How long after starting a relationship would you wait to move in with your partner?
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3. Do you want to get married one day?

4. Would you consider me to be one of your top priorities?
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5. When you think about me and your future, what do you imagine?
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6. Do you see yourself falling for me?

7. What things do you think someone has to know about you before they get in a relationship with you?
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8. How do you feel about the status of our relationship?
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9. Are you dating anyone else?

10. Are a lot of your friends married or in serious relationships?
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11. What was your last relationship like?
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12. Have you told any of your friends about me yet?

13. How do you feel about long-term relationships?
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14. What do you think about dating multiple people at a time?
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15. Are you looking for a girlfriend at the moment?

16. What things do you think we have in common?
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17. What’s the most important thing in a relationship to you?
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18. When do you consider a relationship exclusive?

19. Deep down, how do you feel about me?
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20. What excites you about us?
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21. How do you describe your ideal partner?

22. How do you best communicate?

23. When were you the proudest of yourself?

Serious questions to ask a guy to get to know him

The deep questions allow us to move from shallow to deep interactions. If you want to know someone beyond just the surface, these good questions will do the job.

If the conversation starts to get really deep, this article on how to have deep conversations can be a good guide for you to have in mind.

1. What are you most grateful about in life?
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2. Are you religious?
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3. What/who is your biggest motivator?

4. What’s your biggest achievement so far?
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5. What’s the kindest thing a stranger has ever done for you?
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6. If you were given $20,000 dollars right now, what would you do with it?

7. What’s your definition of a perfect Sunday?
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8. Would you consider yourself an introvert or an extrovert (or both)?
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9. Do you see yourself settling in another country?

10. Would you consider yourself a family-oriented person?
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11. How do you start your day/week?
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12. Do you have any hobbies?

13. If there was one thing you could change about yourself, what would it be?
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14. Are you interested in politics?
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15. What sets you apart from everyone else?

16. What is your dream job?
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17. Do you cook?
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18. Are you confrontational?

19. What is one thing people always misunderstand about you?
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20. What’s your biggest regret in life?
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21. What one word best describes you?

22. How do you feel when you’re around me?
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23. What is your spirit animal and why?
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24. Do you have any children?

25. Who/what is your favorite author/book?
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26. Do you like spending time with friends or alone?
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27. How long can you go without your phone?

28. Which app do you use the most?
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29. What is on your bucket list for this year?
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30. Which phase of your life was the worst?

Random questions to get to know a guy

These random questions will get him talking about the great and interesting stories that would normally never come up in conversations.

1. What is the kindest thing you have ever done?
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2. What is the scariest thing you’ve ever done?
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3. What’s your favorite childhood memory?

4. You can only choose one thing: fast forward the clock 10 years or rewind the clock 10 years?
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5. Would you consider yourself romantic?
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6. Do you prefer bars or clubs?

7. Are you a sports or books kinda guy?
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8. Do you have siblings?
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9. What’s the biggest risk you have ever taken?

10. If there’s anywhere in the world you could go, where would you go?
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11. Do you have any collections (shoes, watches, art pieces)?
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12. If there was one thing you could change about yourself, what would it be?

13. In high school, did you ever get detention?
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14. When was the last time you cried?
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15. Do you prefer dogs or cats?

16. Would you rather be rich or famous?
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17. Would you say you are an adventurer?
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18. Would you travel or move to another country for love?

19. What is your idea of a weekend getaway?
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20. What is at the top of your bucket list?
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21. Mountains or the ocean?

22. Who is your favorite TV character?
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23. What movie have you watched more than 5 times?
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24. If you had to lose one sense which one would you lose?

25. What is the last thing you looked up on Google?
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26. Gym or home workouts?
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27. Do you believe in horoscopes?

28. What is your hidden talent?
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29. Have you ever ditched a date?
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30. Do you think robots will take over the world one day?

31. If you could send a letter to anyone and they were going to read it, who would you write to?

Funny questions to ask to get to know a guy

Not only will these help you get to know him deeper, but they will also get you both laughing.

1. What is the pettiest reason you have refused to date someone?
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2. If you could swap lives with anyone, who would you want to swap with?
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3. What would you do if you got to be Jay-Z for a day?

4. Would you rather be invisible or be able to read people’s minds?
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5. What is your funniest drunk story?
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6. Have you ever had a night out and not remembered anything that happened the day after?

7. What is the first lie you have ever told?
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8. Have you ever gotten in trouble with your parents when you were a kid? What did you do?
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9. Have you ever been arrested?

10. Have you ever questioned your sanity before and why?
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11. If you had a rare disease, would you let scientists freeze you until they found a cure?
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12. Tell me a really really stupid joke that has made you laugh before?

13. Have you ever had an out-of-body experience?
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14. Singing or dancing?
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15. If your life was a movie, what would be the theme song/title and why?

16. What is that one song you are embarrassed to sing in public but know all the lyrics to?
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17. What is the most unprofessional thing you have ever done?
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18. What is your worst pickup line?

19. Love or money?
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20. Have you ever successfully used a pickup line on someone?
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21. If you could be a food, what would you be and why?

22. Who is the one person you would like to marry right now?
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23. Who was your childhood celebrity crush?
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24. What’s the most embarrassing thing you have been caught doing?

25. If you never had to work in your life, what would you do with your time?
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26. Where do you see yourself an hour from now?
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27. Do you think toilet paper should go over or under?

28. Would you rather win a Grammy or be famous on TikTok?
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29. Which social media platform will you never use?
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30. What word have you always mispronounced?

For more inspiration, check out this list of funny questions to get to know someone

Questions to ask a guy you just met

Getting the conversation going with someone you just met can be awkward. Thankfully, these basic questions will come to the rescue. These will help you know him from the surface before you dive into the deep stuff.

1. What’s your favorite hobby?
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2. What is something you cannot go the whole day without?
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3. What is the most spontaneous thing you’ve done lately?

4. What’s your biggest pet peeve?
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5. What’s your favorite beer?
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6. What’s one thing that bothers you most about the world today?

7. Do you have any pets?
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8. Do you prefer summer or winter?
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9. Can you swim?

10. If you could tell your younger self something, what would it be?
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11. When you were younger, what did you want to be?
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12. What song makes you unconditionally happy?

13. What food can you not live without?
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14. Where is your favorite place to eat?
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15. What is the most adventurous thing you have ever done in your life?

16. What is your favorite ice cream flavor?
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17. What is your favorite place to visit?
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18. What type of music do you listen to?

19. Do you prefer movies or series?
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20. Do you have a favorite movie?
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21. Are you religious?

22. Are you in a relationship?
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23. Android or IOS?
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24. What is your favorite sport?

25. If you could visit any part of the world, where would you go?
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26. How do you spend your alone time?
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27. What did you study at school?

28. Where did you study?
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29. Where did you grow up?
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30. What is your favorite holiday?

You also might like this article on how to talk to strangers without being awkward.

Questions to ask a guy before dating

Use these questions to get to know him deeper before you decide to date him.

1. What do you expect to see in a potential partner?
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2. Why did your last relationship end?
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3. What is your idea of a perfect date?

4. Do you believe in love at first sight?
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5. Do you have any female best friends?
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6. Who should pay for the first date?

7. Do you believe in splitting the bill 50/50?
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8. Do you believe in fate?
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9. What is your biggest fear?

10. Would you ever go to a nude beach?
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11. Do you have any political party preferences?
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12. Have you always had the same political beliefs?

13. What is the biggest change you have ever made that you are most proud of?
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14. Tell me your biggest love regret?
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15. What’s your worst breakup story, if you don’t mind sharing?

16. What keeps you motivated?
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17. When in despair, what or who do you go to for help?
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18. What is that one trait you wish you had?

19. In five words, how would your best friend describe you?
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20. What is your motto in life?
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21. Where would you like to settle?

22. How do you spend most of your time?
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23. What do you think is the biggest global problem today?
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24. What is your favorite holiday tradition?

25. What fictional place would you like to visit?
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26. What is the one thing you have ever done because of FOMO and then regretted?
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27. What made you decide to work in the field you are currently working in?

28. What is one annoying thing you hate about restaurants?
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29. Do you have doubts about anything?
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30. Do you prefer giving to charities or directly to the underprivileged?

Questions to ask a guy before a relationship

Making the decision to date someone requires sufficient thought and consideration. These good questions will help you know him personally before you make the decision to be intimately involved with him.

1. Where do you stand regarding commitment?
&nbsp
2. How long after starting a relationship would you wait to move in with your partner?
&nbsp
3. Do you want to get married one day?

4. Would you consider me to be one of your top priorities?
&nbsp
5. When you think about me and your future, what do you imagine?
&nbsp
6. Do you see yourself falling for me?

7. What things do you think someone has to know about you before they get in a relationship with you?
&nbsp
8. How do you feel about the status of our relationship?
&nbsp
9. Are you dating anyone else?

10. Are a lot of your friends married or in serious relationships?
&nbsp
11. What was your last relationship like?
&nbsp
12. Have you told any of your friends about me yet?

13. How do you feel about long-term relationships?
&nbsp
14. What do you think about dating multiple people at a time?
&nbsp
15. Are you looking for a girlfriend at the moment?

16. What things do you think we have in common?
&nbsp
17. What’s the most important thing in a relationship to you?
&nbsp
18. When do you consider a relationship exclusive?

19. Deep down, how do you feel about me?
&nbsp
20. What excites you about us?
&nbsp
21. How do you describe your ideal partner?

22. How do you best communicate?
&nbsp
23. When were you the proudest of yourself?

If you are really into a particular guy, you might be interested in these questions to ask a guy you like

Questions to ask a guy before dating

Use these questions to get to know him deeper before you decide to date him.

1. What do you expect to see in a potential partner?
&nbsp
2. Why did your last relationship end?
&nbsp
3. What is your idea of a perfect date?

4. Do you believe in love at first sight?
&nbsp
5. Do you have any female best friends?
&nbsp
6. Who should pay for the first date?

7. Do you believe in splitting the bill 50/50?
&nbsp
8. Do you believe in fate?
&nbsp
9. What is your biggest fear?

10. Would you ever go to a nude beach?
&nbsp
11. Do you have any political party preferences?
&nbsp
12. Have you always had the same political beliefs?

13. What is the biggest change you have ever made that you are most proud of?
&nbsp
14. Tell me your biggest love regret?
&nbsp
15. What’s your worst breakup story, if you don’t mind sharing?

16. What keeps you motivated?
&nbsp
17. When in despair, what or who do you go to for help?
&nbsp
18. What is that one trait you wish you had?

19. In five words, how would your best friend describe you?
&nbsp
20. What is your motto in life?
&nbsp
21. Where would you like to settle?

22. How do you spend most of your time?
&nbsp
23. What do you think is the biggest global problem today?
&nbsp
24. What is your favorite holiday tradition?

25. What fictional place would you like to visit?
&nbsp
26. What is the one thing you have ever done because of FOMO and then regretted?
&nbsp
27. What made you decide to work in the field you are currently working in?

28. What is one annoying thing you hate about restaurants?
&nbsp
29. Do you have doubts about anything?
&nbsp
30. Do you prefer giving to charities or directly to the underprivileged?

Questions to ask a guy before a relationship

Making the decision to date someone requires sufficient thought and consideration. These good questions will help you know him personally before you make the decision to be intimately involved with him.

1. When you are upset, do you want to be left alone or comforted?
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2. Do you believe in second chances?
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3. What did your past relationship teach you?

4. What is the craziest thing you have done for love and would do it again?
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5. Why are you still single?
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6. Do you think house chores should be divided equally in a relationship?

7. If you were to pick one, what is the most important value you would teach your children: honesty, kindness, or courage?
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8. Would you sing on karaoke night?
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9. Name a bad quality you wouldn’t mind in a partner?

10. Name one thing about me that you adore and can’t get over?
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11. What is the most special thing that someone has ever done for you?
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12. If you could pick a holiday destination and go there immediately, where would you choose to go?

13. Is financial literacy something that is important to you?
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14. What are your financial goals?
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15. Is cohabiting something you would do?

16. Do you prefer cuddling or kissing?
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17. What is your love language?
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18. How do you express your love to some you love?

19. Do you prefer being the little spoon or the big spoon?
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20. Do you snore?
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21. What’s your secret fantasy?

22. Do you like surprises?
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23. Cats or dogs?
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24. How do you spend most of your money?

25. What habit would you want to get rid of?
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26. What do you want out of our relationship
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27. How do you deal with differences in opinions when in a relationship?

28. What is the one thing you won’t compromise on?
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29. How important is sex to you when you’re in a relationship?
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30. If your partner were financially independent, would you find that intimidating?

Questions to ask a guy on a date

Dates shouldn’t be all about enjoying the food. This list of good questions will help you keep the date more lively, interesting, and engaging while getting to know him at a personal level.

1. What is the red flag you are willing to ignore?
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2. Think about the people you love the most. What do you do for them to show them that you love them?
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3. Are you health conscious?

4. If you could be given a date of death, would you want to know it?
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5. How do you define beauty?
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6. Are you close to any of your family members?

7. Have you ever received flowers?
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8. If your life was a movie or book, what would the title be?
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9. Every day you wake up in the morning, what is your biggest challenge?

10. Where do you find meaning in your life?
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11. Would you rather read the book or watch the movie?
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12. Wnbsphat’s your favorite song and why?

13. What is your favorite game to play on a game night?
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14. Have you ever done karaoke in a public place?
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15. Are you a competitive person when it comes to games?

16. If you were a DJ, what would your DJ name be?
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17. Would you say I’m your usual type?
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18. Do you like physical affection?

19. If you had three wishes, what would they be?
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20. Do you believe in soul mates?
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21. How do you express love when in a relationship?

22. How do you handle stress/anger?
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23. What is your go-to flirting move?
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24. What can a woman do to impress you?

25. Would you rather spend the night at home or go out?
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26. What are your priorities and values in life?
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27. How would you like to enjoy your retirement?

28. At what age would you like to retire?
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29. Do you like the idea of traveling around the world?
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30. Do you consider yourself liberal or conservative?

Viktor is a Counselor specialized in interpersonal communication and relationships. He manages SocialSelf’s scientific review board. Follow on Twitter or read more.

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