Best questions to get to know someone deeply

Too often we get swept up in the chaos and stress of everyday life. Many people get stuck in the monotony of work, eat, sleep and repeat. This routine can make it difficult to have an insightful conversation with your significant other.

Whether you and your love are sharing a quick meal or cuddling before bed, you can use that time to connect on a deeper level. It’s important to take advantage of the little moments throughout the day. We’ve put together a list of 116 deep questions that will spark fun and meaningful discussions.

Just download and print the questions. Then, put them in a jar or attach them with a ring. We’ve added blank pages so that you can write your own, too!

Deep Questions About Childhood

1. What is your best childhood memory?
2. What is your worst childhood memory?
3. What was your biggest fear as a child?
4. What was your favorite year of school?
5. What was your favorite subject/class in school?
6. What did you want to be when you grew up?
7. What was your favorite game to play?
8. What is the single most important thing you learned as a child?
9. What is your most memorable family event?
10. What do you admire most about your parents?
11. What do you look forward to about being a parent?
12. If you don’t want to be a parent, why?
13. Do you want to live near or far from relatives?
14. When your parents get old, how do you plan on taking care of them?

Deep Questions About Love

1. When was the first time you said “I love you” to someone in your life other than family?
2. When and where did you go on your first date ever?
3. Do you remember our first date?
4. Were you nervous during our first kiss?
5. When did you know you loved me?
6. What is your ideal night?
7. What is your favorite thing about me?
8. Do you believe in true love or love at first sight?
9. Do you think people are made for each other?
10. Where is the perfect honeymoon locale?
11. Describe a fun date that only costs $20.
12. Describe the most romantic date you can think of — spare no expense!
13. If you were on a dating game show, what questions would you ask?
14. What is your favorite memory with me?
15. What do you look forward to experiencing with me?
16. Would you rather a night in a fancy penthouse suite or a private beach house?

Deep Questions About Values

1. Would you rather acquire material items or experiences?
2. If it cost the same, would you live in a mansion or a mid-sized house with a lot of land?
3. In what scenario, if any, is it okay to lie?
4. When, if ever, is it okay to break the law?
5. What is the most important lesson to teach a child?
6. How often do you go out of your way to help someone?
7. If you could pick a new “golden rule,” what would it be?
8. What are important societal values? (ex. Democracy, fundamental rights, etc.)
9. How have your values changed from ten years ago?
10. What do you see as your best character trait?
11. If you could change one thing about your character, what would it be?
12. Would you consider yourself a pessimist or an optimist?
13. When were you the most disappointed in yourself?
14. When were you the most proud of yourself?
15. Generally speaking, do you like the way you look?
16. If you could change one thing about the way you look, what would it be?
17. Do you put as much effort and emphasis on inner beauty as outer beauty?

Deep Questions About Goals and Motivations

1. Who in your family do you view as a role model?
2. Are you inspired by any celebrities dead or alive?
3. What thought or object gets you through the day?
4. Do you find praise or criticism to be more motivating?
5. What inspires you to better yourself?
6. What advice would you give to your children to stay determined?
7. What is the best way to motivate each other?
8. What is your greatest success to date?
9. What do you hope to achieve in the short-term?
10. What is your long-term goal?
11. What is your biggest regret?
12. What mistake did you learn the most from?
13. What are you most ashamed of?
14. Is failing less, equal or more important than succeeding?

Deep Questions About Relationships

1. What do you look for in a friendship?
2. What is/was your longest lasting friendship and how did it last so long?
3. Do you think you can have multiple best friends or only one?
4. Do you think your pet can also be your friend?
5. Do you consider your parents as friends?
6. Do you think opposite genders can maintain a friendship without developing a love interest?
7. What is an unforgivable action?
8. What is your advice for long-distance friendships?
9. Do you have different advice for nearby relationships?
10. In your opinion, can long-distance relationships survive?
11. Do you think a couple should split costs?
12. Do you think it’s better to save money or invest?
13. How should household chores be divided?
14. What do you look for in a significant other?
15. What is the most important thing in a relationship? (e.g. trust, respect, etc.)
16. How often should a couple argue or fight to maintain a healthy relationship?

Deep Questions About Life Events

1. What was your best birthday?
2. If you could only celebrate one holiday each year, what would it be?
3. Do you prefer family events or alone time?
4. Provided there is good weather, do you enjoy indoor or outdoor activities?
5. What is your ideal wedding ceremony?
6. Describe your perfect vacation.
7. What is the best concert you’ve ever attended?
8. What events are on your bucket list? (ex. Lollapalooza, Macy’s Thanksgiving Day Parade, etc.)
9. When, where, and how long was the best road trip you’ve ever taken?
10. Would you rather spend a week in New York City or Los Angeles?
11. Have you ever been camping? What was your favorite part?

Deep Questions About Stress

1. Is there anything that gives you overwhelming anxiety?
2. How do you handle high-stress situations?
3. What is the most stress-inducing thing that could happen at work?
4. What helps you decompress?
5. Is there a smell that instantly relaxes you?
6. After a horrible day, would you prefer a nice dinner out or a cozy movie night?
7. Are you terrified of anything fictional? For example, the supernatural or zombies.
8. What is your biggest fear in life?
9. Do you have any phobias?
10. Do you have any irrational fears?
11. What was the worst nightmare of your life?
12. Do you like to pull scary pranks on people?
13. What is the scariest movie you’ve ever seen?

Deep Hypothetical Questions

1. If you could have one superpower, what would it be?
2. Do you think flying or mind reading is a more functional power?
3. If you could have one human talent that you don’t currently have, what would it be?
4. If you had three wishes, what would you wish for? (excluding more wishes)
5. If you had the power to correct one problem in the world, what would you fix?
6. Where would you go if you could teleport anywhere in the world?
7. If you could be an animal for a week, what would you be?
8. If you could be an object for a day, what would you be?
9. What would you do if you won the lottery tomorrow?
10. If you could eat anything you wanted right now, what would you order?
11. You’re going to outer space — what planet do you want to see?
12. If the world ended tomorrow, what would you do on your last day?
13. Would you rather go back in time to see the dinosaurs or jump forward a thousand years to see our futuristic society?
14. If you could make one book or movie a reality, which would you choose?
15. If you could be a character from a hit television show, who would you pick?

There’s no limit when it comes to deep questions to ask your partner. They will often lead to thought-provoking conversations that can tighten your bond. Spruce it up by trying to guess each other’s answers! Pair these conversation starters with a romantic gift or journal, so you can document any surprising things you find out about your partner.

You can also use games to understand your significant other more profoundly. By playing games such as “Desert Island” you might discover something new — learning the three things someone can’t live without is a window into their core personality.

No matter your relationship status, asking deep questions will help you strengthen your romance and companionship.

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