300 Questions to Ask During Courtship

Ready to take your relationship to the next level? Courtship is like a test drive for love, and asking the right questions can help you understand if you’re truly compatible.

From money matters to deep beliefs, get ready to dive into conversations that could shape your future together. So buckle up, and let’s get to know the person who might just be your forever co-pilot!

About Personal Values

  1. What’s most important to you in life?
  2. Do you believe in God or a higher power?
  3. How important is family to you?
  4. What’s your view on marriage?
  5. Do you want kids? How many?
  6. How do you feel about honesty?
  7. What do you think about lying?
  8. What are your thoughts on money and spending?
  9. How do you handle stress or difficult times?
  10. How do you feel about working versus staying home to take care of the family?
  11. What’s your opinion on gender roles?
  12. What are your views on equality in a relationship?
  13. How important is your career to you?
  14. Do you believe in love at first sight?
  15. What do you think makes a relationship last?
  16. How do you handle disagreements or fights?
  17. How do you feel about sharing responsibilities at home?
  18. What’s your take on friendship outside of the relationship?
  19. What’s your opinion on keeping secrets in a relationship?
  20. How do you feel about pets?
  21. What’s your view on politics? Do they matter in a relationship?
  22. How important is physical attraction to you?
  23. How do you feel about social media and relationships?
  24. Do you value alone time?
  25. How do you feel about travel and adventure?
  26. What’s your opinion on celebrating anniversaries or special occasions?
  27. How important is it for you to keep fit or be healthy?
  28. How do you feel about helping others or community service?
  29. What are your thoughts on long-distance relationships?
  30. How important is trust in a relationship for you?

About Life Goals

  1. What’s your dream job?
  2. Where do you see yourself in 5 years?
  3. Where would you like to live in the future?
  4. Do you have any career milestones you want to achieve?
  5. How important is financial stability to you?
  6. What’s one thing you want to accomplish before you die?
  7. Do you have plans for further education or training?
  8. Would you consider moving to another city or country for work?
  9. How do you plan to prepare for retirement?
  10. Are you interested in starting a business?
  11. What are your hobbies, and do you want to invest more time in them?
  12. How do you feel about work-life balance?
  13. Would you like to write a book or create something lasting?
  14. Do you have any travel goals?
  15. Are there any skills you’d like to learn or improve?
  16. How do you feel about becoming famous or well-known?
  17. Would you want to go back to school at some point?
  18. How do you plan on staying healthy as you get older?
  19. Are there any big risks you want to take in life?
  20. Do you have any mentors or people you look up to?
  21. Is early retirement a goal for you?
  22. Would you like to get involved in politics or social causes?
  23. What’s a dream you’ve had since you were a kid?
  24. Do you want to own a home, or are you okay with renting?
  25. How important is it for you to be close to your extended family as you get older?
  26. Do you want to live in the countryside, city, or somewhere in between?
  27. Would you consider going on a long journey or adventure together?
  28. Do you have any spiritual goals?
  29. How do you feel about taking care of parents when they’re older?
  30. Do you have a “bucket list“? What’s one thing on it?

About Future Plans

  1. Do you want a big wedding or a small one?
  2. How soon would you want to get married?
  3. When do you think is the right time to meet each other’s families?
  4. How long would you want to be engaged before getting married?
  5. What’s your idea of a dream honeymoon?
  6. Are you open to couples therapy if we ever need it?
  7. Would you be willing to go through tough times financially for a bigger payoff later?
  8. Do you want to live near your family, or are you open to living anywhere?
  9. How often do you want to go on vacations?
  10. How do you feel about joint bank accounts?
  11. Do you want to have kids right away or wait?
  12. What are your thoughts on adoption?
  13. How do you want to raise your kids in terms of religion and values?
  14. Would you stay at home with the kids if needed?
  15. How do you feel about homeschooling?
  16. How many children do you want to have?
  17. Would you ever consider being a stay-at-home mom/dad?
  18. How do you want to celebrate holidays?
  19. Would you want to have a date night regularly?
  20. What traditions do you want to start as a couple or family?
  21. How do you feel about traveling abroad for extended periods?
  22. Would you ever want to work together on a business or project?
  23. How often do you think we should visit our extended families?
  24. Would you be okay with moving if I got a job offer in another place?
  25. How do you feel about caring for a pet together?
  26. Are there any places where you’d never want to live?
  27. Do you want to eventually settle down in one place or keep moving?
  28. How do you feel about getting older and potentially retiring together?
  29. Do you have any end-of-life wishes or plans?
  30. How would you handle it if one of us had to take a job with lots of travel?

About Hobbies and Interests

  1. What’s your favorite way to relax after a long day?
  2. Do you have a go-to movie or TV show?
  3. What kind of music really gets you in a good mood?
  4. Do you enjoy reading? What’s the last book you read?
  5. What’s your favorite sport to watch or play?
  6. Do you like cooking or baking?
  7. Do you have a favorite type of cuisine?
  8. Are you into video games?
  9. Do you enjoy outdoor activities like hiking or camping?
  10. What’s your favorite type of workout or exercise?
  11. Do you have a hobby that you’ve always wanted to pick up but never did?
  12. What’s your idea of a fun weekend?
  13. Are you into arts and crafts?
  14. Do you like attending live events like concerts or sports games?
  15. How do you feel about board games or puzzles?
  16. What’s your favorite season and why?
  17. Do you like to dance?
  18. Are you into photography or any other visual arts?
  19. What’s a place you’ve always wanted to visit?
  20. Are you a morning person or a night owl?
  21. Do you like gardening or growing things?
  22. How do you feel about DIY projects?
  23. Do you have a favorite museum or type of art?
  24. Are you into any unusual or unique hobbies?
  25. Do you like to write or journal?
  26. How do you feel about extreme sports or adventures?
  27. Do you enjoy watching documentaries?
  28. Are you a fan of any podcasts or YouTube channels?
  29. What’s your favorite way to celebrate your birthday?
  30. Do you like thrift shopping or finding unique items?

About Family and Friends

  1. How close are you to your family?
  2. How often do you see or talk to your parents?
  3. Do you have any siblings? What’s your relationship like with them?
  4. Are there any family traditions you really enjoy?
  5. What role do your friends play in your life?
  6. Do you have a best friend? How long have you known them?
  7. How do you handle disagreements with family or friends?
  8. How important are family gatherings to you?
  9. Do you like to spend the holidays with family?
  10. Would you consider your family to be tight-knit or more laid-back?
  11. Do you have a group of friends you regularly hang out with?
  12. How do you feel about mixing friend groups or bringing friends into family events?
  13. Do you have any childhood friends you’re still close to?
  14. Are you the type to have a few close friends or lots of acquaintances?
  15. How do you feel about your partner having close friends of the opposite sex?
  16. Do your friends and family generally get along?
  17. What’s the most important lesson you’ve learned from your family?
  18. How do you celebrate family milestones like birthdays or anniversaries?
  19. Have you ever had a falling out with a friend or family member?
  20. How would you handle it if your family didn’t like your partner?
  21. Do you think friends can become like family?
  22. How often do you like to catch up with old friends?
  23. Are you a godparent, or do you have a godchild?
  24. What values do you share with your family?
  25. How do you feel about family vacations?
  26. Would you want to live close to your family after getting married?
  27. Are there any family recipes you love?
  28. How do you handle family pressures or expectations?
  29. Do you have any family heirlooms or traditions you’d like to pass on?
  30. How would you introduce me to your friends and family?

About Finances

  1. How do you budget your money?
  2. What’s your attitude towards saving?
  3. Do you have any debt? How do you feel about it?
  4. Are you a spender or a saver?
  5. How do you feel about joint finances in a marriage?
  6. Do you invest in stocks, real estate, or anything else?
  7. What are your financial goals for the next few years?
  8. How do you feel about lending money to friends or family?
  9. Do you believe in having separate bank accounts in a marriage?
  10. What’s your approach to paying bills?
  11. Do you have any financial deal-breakers in a relationship?
  12. How would you handle a large windfall of money?
  13. Are you comfortable discussing finances openly?
  14. How important is your partner’s income to you?
  15. What are your thoughts on spending money on luxury items?
  16. Do you follow a strict budget, or are you more flexible?
  17. How would we handle finances if one of us lost our job?
  18. What are your thoughts on retirement funds and planning?
  19. How do you prioritize your spending? (Necessities, fun, investments?)
  20. What’s your outlook on charitable giving or tithing?
  21. How would you handle unexpected medical expenses?
  22. Do you have a financial advisor, or do you manage your money yourself?
  23. How would you teach our children about money?
  24. How do you feel about taking financial risks?
  25. Would you be willing to make career sacrifices for the benefit of our family’s finances?
  26. How important is it for you to own a home?
  27. Do you have any expensive hobbies that you feel strongly about maintaining?
  28. What’s your take on holiday and gift spending?
  29. Do you have financial obligations to anyone outside of our relationship?
  30. How would we decide on big purchases, like a car or a house?

About Communication Styles

  1. How do you usually handle disagreements?
  2. Do you like to talk things out right away or take time to cool off?
  3. Are you more of a texter, or do you prefer phone calls?
  4. How do you like to resolve conflicts?
  5. How open are you about your feelings?
  6. When you’re upset, do you want space or attention?
  7. How do you show affection? Words, actions, gifts, or time?
  8. Are you comfortable talking about difficult topics?
  9. How do you handle criticism?
  10. What’s your go-to way to apologize?
  11. Do you find it easy or hard to say “I love you“?
  12. Are you more of a listener or a talker?
  13. How important is body language to you?
  14. Do you appreciate directness or do you prefer things to be sugarcoated?
  15. How do you feel about public displays of affection?
  16. What makes you feel truly heard and understood?
  17. How do you like to celebrate good news?
  18. How do you feel about discussing our relationship with others?
  19. Do you think it’s important to check in with each other daily?
  20. How do you express support for each other’s goals or dreams?
  21. Do you find it easy to ask for help?
  22. What makes you feel appreciated?
  23. How comfortable are you with silence?
  24. Are you okay with discussing your fears and insecurities?
  25. How do you give compliments?
  26. Do you feel like you’re good at reading people’s emotions?
  27. How would you let me know if something I did bothered you?
  28. How do you feel about discussing past relationships?
  29. How do you communicate when you’re stressed?
  30. How would you like us to handle disagreements in public?

About Past Relationships

  1. What did you learn from your last relationship?
  2. How long was your longest relationship?
  3. What’s the most important lesson you’ve taken away from past relationships?
  4. How do you know when you’re ready to move on after a breakup?
  5. Have you ever been in a long-distance relationship?
  6. What’s a deal-breaker for you in a relationship?
  7. Have you ever lived with a romantic partner?
  8. Do you remain friends with your exes?
  9. Have you ever had your heart broken?
  10. What’s your philosophy on breakups? Clean break or staying in touch?
  11. Have you ever gone back to an ex? Why?
  12. Were any of your past relationships affected by differences in religion, culture, or background?
  13. Have you ever felt like you settled in a past relationship?
  14. What was the hardest part about your most difficult breakup?
  15. Have you ever been in a relationship where trust was broken?
  16. Do you think it’s important to have closure from past relationships?
  17. Have you ever had to end a relationship, and how did you handle it?
  18. What’s something you wish you had done differently in past relationships?
  19. Have you ever been in a relationship where you felt you had to change who you are?
  20. How soon after a breakup do you usually start dating again?
  21. How do you handle jealousy in a relationship?
  22. Have you ever been in a relationship that moved too fast or too slow for you?
  23. Did your past relationships end amicably or was it usually messy?
  24. What role did family and friends play in your past relationships?
  25. Have you ever taken a break in a relationship?
  26. How have you changed since your last relationship?
  27. Have you ever rushed into a new relationship right after a breakup?
  28. What are your thoughts on rebound relationships?
  29. Do you have any regrets about past relationships?
  30. How did you handle balancing time for yourself and time with a partner in past relationships?

About Career Ambitions

  1. What’s your dream job?
  2. How important is your career to you?
  3. Do you have a career plan for the next few years?
  4. Would you be willing to relocate for a job?
  5. How do you handle work-related stress?
  6. What’s a typical workday like for you?
  7. What are you most proud of in your career so far?
  8. What would be a reason for you to quit a job?
  9. How do you feel about working weekends or long hours?
  10. Do you like to keep your work life and personal life separate?
  11. Have you ever thought about starting your own business?
  12. What skills or qualifications do you want to acquire in the next few years?
  13. How do you handle criticism at work?
  14. What do you enjoy most about your current job?
  15. Do you have a mentor or someone who has greatly influenced your career?
  16. What’s more important to you: the work you do or the income you earn?
  17. How competitive are you in your career?
  18. What would be your ideal work environment?
  19. Would you consider going back to school to further your career?
  20. Do you aspire to be a manager or leader in your field?
  21. How do you balance work with personal time?
  22. Have you ever had to make a difficult choice between your career and personal life?
  23. What’s a career milestone you aim to reach?
  24. How do you stay updated or continue learning in your field?
  25. Would you take a job with fewer hours if it meant less pay?
  26. What’s the toughest decision you’ve ever had to make in your career?
  27. How do you handle conflicts with colleagues?
  28. Do you have any side hustles or passion projects?
  29. What’s the biggest risk you’ve taken in your career?
  30. How would you feel about supporting a family on your income alone?

About Religion and Beliefs

  1. What role does religion or spirituality play in your life?
  2. How important is it for you that your partner shares your religious beliefs?
  3. Do you attend religious services regularly?
  4. How do you practice your faith day-to-day?
  5. What are your beliefs about life after death?
  6. Would you want a religious ceremony for your wedding?
  7. How would you like to raise kids when it comes to religion?
  8. What religious or spiritual texts do you find important?
  9. Do you have any religious dietary restrictions?
  10. Are there religious holidays you observe?
  11. How do your family and friends feel about your religious beliefs?
  12. Have your beliefs changed over time?
  13. How do you feel about interfaith relationships?
  14. Would you consider going to religious services together?
  15. What values do you hold most dear from your religious or spiritual background?
  16. How would you handle religious differences in a relationship?
  17. Are there any religious practices you’d never engage in?
  18. How do you feel about discussions on religion and spirituality?
  19. What does prayer or meditation mean to you?
  20. How do you feel about religious or spiritual symbols and rituals?
  21. Are there any ethical principles that guide you, religious or otherwise?
  22. How do you reconcile science and religion, if at all?
  23. Have you ever been on a religious or spiritual retreat?
  24. Do you believe in destiny or fate?
  25. How do you feel about moral issues like abortion or capital punishment?
  26. Would you consider yourself more religious, spiritual, both, or neither?
  27. How do you feel about religious charities or mission work?
  28. Do you believe in a higher power?
  29. How do you feel about religious traditions in your culture?
  30. How would you support a partner with different religious beliefs?

Frequently Asked Questions

What if we’re uncomfortable discussing finances?

Finances can be a tricky subject, but they’re crucial for long-term planning. If it feels too awkward, you might start with general questions and gradually move to specifics as comfort grows.

Is it a bad sign if we argue while discussing these topics?

Not necessarily. Disagreements can be healthy and provide a window into how you both resolve conflict. The key is to argue fairly and constructively.

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Bea Mariel Saulo

Bea is an editor and writer with a passion for literature and self-improvement. Her ability to combine these two interests enables her to write informative and thought-provoking articles that positively impact society. She enjoys reading stories and listening to music in her spare time.