Hard Questions to Make Him Think

1. If you could fix one world problem, what would it be?

2. If you could live in any era, which would it be and why?

3. What advice would you give to a person who is just graduating high school?

4. If you could have chosen your own name, what would you have picked?

5. If your home was on fire and you only had time to grab 3 things, what would they be?

6. If you became famous, would you enjoy the limelight or miss your privacy?

7. If you had $200 to spend on something special just for me, what would you buy?

8. If you had three wishes, what would they be?

9. If you were told you have a terminal illness, how would you take the news?

10. If you only had a week left to live, what are some things you would do?

11. Would you sacrifice yourself for a stranger?

12. If a family member needed a kidney and you were the only match, would you give
one up?

13. If I wanted a puppy for my birthday, would you adopt a purebred from a breeder or a
mix from a shelter?

14. You suspect that your neighbors may be abusing their child, do you mind your own
business or call the police?

15. If I went missing, my body never recovered, would you move on or devote your life to
looking for me? If you did move on, how long would you wait?

16. If you could invite 3 people to dinner, who would they be?

17. If you could live til you were 90 and either have the mind or body of a 30-yr-old,
which would you choose and why?

18. If you could wake up tomorrow and have gained one ability, what would it be and
why?

19. If a crystal ball could tell you the truth about your life, me, or the future, what would
you want to know?

20. If you could live anywhere, where would you live?

Personal Questions to Learn About
How He Sees Himself and What
He’s Like Inside
1. Which one fits you better? "Live for the moment", or "Save the best for last"?

2. What's your favorite thing about yourself?

3. If you could change anything about yourself, what would it be?

4. Do you prefer going out or staying in?

5. Would you consider yourself an externally motivated or internally motivated person?

6. How do you deal with failure?

7. Do you put more attention to the people around you or the things around you?

8. When things break, do you prefer to fix them or replace them?

9. Would you consider yourself materialistic?

10. What would you consider a perfect day?

11. What would you consider a perfect day?

12. What would be your perfect date night?

13. What are some things that offend you?

14. What is one thing that you cannot start your day without?

15. If you’re stressed out, what helps you wind down?

16. When you die, do you want to be buried or cremated? Why?

17. What inspires you?

18. Would you consider yourself an optimist, pessimist, or realist?

19. We notice an old man living out of a shopping cart behind a grocery store. What is
your first thought about him?

20. Someone calls me something horrible. Do you let me fight my own battles, or jump in
and defend me?

21. Do you think it's okay to have a close female friend at work?

22. What are three things you are willing to splurge on for yourself?

23. What's something that no one else knows about you?

24. Do you ever rehearse a phone call beforehand?

 25. When did you last sing to yourself? To someone else?

26. What are you most thankful for?

1. What do you most fear about getting older?

Questions to Know More About His

Past
1. Have you ever done something you regretted?

2. Where do you see yourself in five years?

3. What is your happiest memory?

4. When was the last time you shed a tear?

5. What is a tradition you did as a child that you want to do with your kids someday?

6. What are some things in life that you had to learn the hard way?

7. Do you have any dreams from childhood that you can vividly recall?

8. What were your childhood aspirations, and how have they changed?

9. How do you picture your life when you're 60?

10. What is your most terrible memory?

11. How have you changed the most since you were younger?

12. In what areas do you want to change the most?

13. When was the first time you were in love?

14. When was the first time you said I love you?

15. Is there any book that changed your life?

16. What is your biggest insecurity?

17. Is there anything you’re ashamed of?

18. Is there anything you wouldn’t want your family to know?

19. If you could change anything about the past, what would it be?

Political Questions
1. Why do you think the divorce rate is so high nowadays?

2. What do you think is the biggest flaw of the welfare system?

3. If you were running for president, what are three key things you would include in your
campaign?

4. Are you pro-choice or pro-life?

5. How do you feel about genetically modified food?

6. What is one thing that you feel would make any small business owner more
successful?

7. What invention do you think has done the most for the human race?

8. Should children be allowed to have cell phones?

9. Do you think a person’s outward appearance says anything about who they are as a
person?

10. How important do you think it is to do well in school?

11. Would you consider yourself proud to live in this country?

12. Is there anything too serious to be joked about?

13. What are your views on the political system?

Questions to Learn How He Feels

About Relationships
1. What is your position on premarital sex?

2. What do you look for most in a spouse?

3. What religious/spiritual views do you have and why?

4. How important is it for you to save money?

5. How important is it for you to invest money?

6. How important do you think sex is in a marriage?

7. If one of us had to move far away, would you be able to handle a long distance
relationship?

8. What is one thing that can destroy a relationship and never be forgiven?

9. Do you want to have kids someday when you meet the right person?

10. Do you think it’s more important to work or spend time with family?

11. What are three key elements in every successful relationship?

12. Do you think people can or should be friends with their exes?

13. Do you believe emotional 'cheating' is just as bad as real cheating?

14. What do you think of open relationships?

Questions to Learn About Your

Relationship and How He Feels
About You
1. When did you first realize you wanted to be with me?

2. Are you looking for commitment?

3. What was your first impression of me?

4. Would you surprise me with an expensive gift, or would you consult me before
spending the money on it?

5. Would you rather I be good in the kitchen or good in the bedroom?

6. What do you think is more admirable, a stay-at-home mom or a career driven mom?

7. Would you rather leave a big impact on the world or a big impact in your family?

8. What song do you think best fits our relationship?

9. What famous real or fictional couple reminds you the most of us?

10. Do you think a proposal should be a grand public display or a private intimate
moment?

11. If we had children, what features would you want them to get from you and which
from me?

12. What is something you appreciate about me?

13. What do you think are three things we have in common?

14. What are the biggest differences between us?

15. Is there anything in our relationship that you think we need to work on?

16. What’s something you could never compromise about?

Deep, Serious, and Spiritual

Questions
1. Do you believe in heaven?

2. Do you believe in soulmates?

3. Do you forgive and forget or forgive and remember?

4. If you had kids, what would be your biggest hope and biggest fear for them?

5. What is one area in your life where you feel like something is missing?

6. Do you believe there is good in everyone?

7. Do you think your significant other can be both your best friend and your lover?

8. Do you think it’s better to have the worst house in a nice neighborhood or the best
house in a bad neighborhood?

9. Is life anything like you had pictured it would be growing up?

10. Would you rather have a life full of love or a life full of money?

11. Can a positive outlook make any situation better?

12. Do you think children are more of a blessing or a burden?

13. Do you believe in the phrase "opposites attract"?

14. Who are three people in your life that you would risk dying for?

15. If I was giving birth to our child and complications arose that meant only one of us
would make it, who would you save?

16. What would you want said about you after you die?

17. If you could go back in time to give advice to your younger self, what would you say?

18. What is your life story?

19. What roles do love and affection play in your life?

20. Complete this sentence: “I wish I had someone with whom I could share . . . .”

21. If you died tonight, is there anything you’d regret not having told someone?

22. Of all the people in your family, whose death would you find most disturbing and
why?

23. What’s a problem you’re dealing with right now?

24. What’s the biggest struggle that you’ve ever faced?

25. Would you let me help you with your biggest problems?