Key Takeaways
- Playing the 21 Questions game helps partners discover each other's core beliefs and deepens emotional bonds.
- Establish a judgment-free zone before starting the 21 Questions game to encourage honest and open communication.
- Mix deep questions with light-hearted topics in the 21 Questions game to keep it engaging and balanced.
When you first start seeing someone, it can be difficult to know what to do—or say. Whether you're on your first or fifth date, you may struggle to find the right conversation topic. Instead of discussing your upcoming weekend plans for the third time, consider participating in a lively activity that will uncover new pieces of information about your partner: the 21 questions game. While there are different ways to play this game, it's ultimately about asking interesting and thought-provoking inquiries that allow you to get to know someone on a deeper level, an essential component for building and maintaining a healthy relationship. And even if you and your partner have been together for years, this game can still help strengthen your bond.
In the early phases of dating, it can feel uncomfortable to ask the person you're seeing personal questions about their family, values, and goals. However, understanding who they are, what they think, and where they come from is essential in order to see if you two have the foundation for a relationship. By playing the 21 questions game, you can cover all of the topics that you've been too nervous to bring up—from their views on marriage and whether they want kids to their career goals and biggest stressors. However, no game is complete without some out-of-the-box inquires. In addition to selecting questions that unlock more of your partner's psyche, consider throwing in a few light-hearted options. Knowing their favorite movie, guilty pleasure, or go-to meal is often just as important.
Ahead, we put together a simple guide to playing the 21 questions game, in order to help you understand the deepest parts of your significant other. Read on for more.
Why You Should Play 21 Questions With Your Partner
"When we are able to be emotionally available and emotionally exposed, we are able to feel a connection with someone," says Shaakira Haywood Stewart, Ph.D., a licensed psychologist based in New York. "We are able to experience their world a little bit more and that draws us closer to them." Questions that tap into these vulnerabilities cause us to be "emotionally exposed," which in turn, encourages curiosity, deepens emotional bonds, wards off insecurities, and promotes healthy communication skills. If you're seeing someone new, asking questions early on is the best way to learn more about them, allowing you to assess whether or not you'd like to continue dating.
How to Play the 21 Questions Game
Before starting the game, establish with your partner that this is a judgment-free zone where both of you can speak openly. To ensure you can truly tap into your connection, try to keep all distractions to a minimum; put your phone on silent, and turn off the TV.
There are multiple ways to play this game. You and your partner can take turns asking one another questions until you've each answered 21, or you can ask one person all 21 questions before switching. You can also play this game with a group of people. Go around in a circle and have everyone answer one question at a time, or put someone in the "hot seat" and have them answer all 21 at once. Regardless of the way you choose to execute the game, the most essential component is that everyone ultimately answers 21 questions.
170 Questions to Considering Using
If you're looking for some potential questions, consider selecting 21 from our list of 170 below. These inquires cover a wide range of topics, ensuring that you get to know your partner on a deeper level.
Best Family-Related Questions to Ask
- What holiday is most important to your family?
- Do you want kids?
- What's your happiest childhood memory?
- How often do you speak to your family?
- How important is your family to you?
- What's your relationship with your parents like?
- What family tradition do you love the most?
- What would you change about your family if you could?
- How do you feel about your hometown?
- If given the option, would you move back to your hometown?
- Are you closer with one of your parents?
- Are you close with your siblings?
- In an emergency, which family member would you call?
- Who would you trade places with in your family?
- Who in your family do you admire the most?
- Does your family have a nickname for you?
- How often do you see members of your extended family?
- What's your favorite thing about your family?
- Which family member are you the most similar to?
- What's your role in your family dynamic?
- What's the biggest lie you've ever told your parents?
- What was the biggest lesson you've learned from an older family member?
- Do you have any family heirlooms?
Best Deep Questions to Ask
- What are your core beliefs?
- What role do your core beliefs play in your life?
- How would you define your worldview?
- Are you an optimist or a pessimist?
- Who is your favorite person to call?
- What are your career goals?
- How do you maintain work-life balance?
- What are your personal goals?
- What three accomplishments are you the most proud of?
- What's the hardest life lesson you've had to learn?
- How do handle stress?
- When was the last time you were wrong in a situation? How did you handle it?
- How do you get out of a funk?
- How would you handle a situation at work where you were asked to execute a task that went against your morals?
- When you do you feel most like yourself?
- What advice would you give your 10-year-old self?
- What charitable cause is most important to you?
- What's your biggest fear?
- Who's your idol?
- How important is spending time alone to you?
- What was your biggest insecurity as a child?
- What's your biggest failure?
- How would your friends describe you?
- What do you hope to accomplish in the next 10 years?
- What's been the scariest moment of your life?
- Have you ever been in an emergency situation?
- If you could change anything about yourself, what would it be?
- Whose opinion do you trust most?
- Who do you go to for advice?
- What's the hardest decision you've ever had to make?
- What book had the biggest impact on your life?
- How do you want to be remembered?
- What does success look like to you?
- What's the best piece of advice you've ever heard?
- What does happiness look like to you?
- What does your dream life look like?
- Are you a trusting person?
- What's the kindest thing someone has ever done for you?
- Do you think of yourself as a leader or a follower?
- What's your favorite characteristic about yourself?
- What's on your bucket list?
- What scares you the most about the future?
- What's your most embarrassing moment?
- Are you afraid of death?
- If you could, would you want to know the date of your death?
- What's the worst way to die?
- Who would you want to give the eulogy at your funeral?
- Who in your life do you worry about the most?
- What gives you the most stress in life?
Best Light-Hearted Questions to Ask
- What's your favorite holiday?
- If you had a free Saturday, what are three activities you would want to do?
- Do you prefer to text or call people?
- If you had complete financial freedom, how would you spend your time?
- Do you consider yourself a morning bird or a night owl?
- Who's your favorite musical artist?
- Do you prefer to stay indoors or spend time outside?
- What is your happy place?
- Imagine you were trapped in a TV show for a week. What character would you be?
- If you were having dinner and could invite five celebrities, who would you invite and why?
- Do you procrastinate tasks or tackle them right away?
- Where would you head on your dream vacation?
- What was your best vacation?
- Do you prefer to adventure or relax on vacation?
- How would you define your personal style?
- If you could trade places with anyone for a day, who would it be?
- What's your weirdest habit?
- Do you believe in astrology?
- What's your favorite movie?
- What's your favorite book?
- If you could travel to space, would you take the opportunity?
- What app on your phone do you use the most?
- What celebrity do you think you'd be friends with?
- If you could live anywhere in the world, where would it be?
- What's your favorite piece of clothing in your closet?
- Do you consider yourself to be a good cook?
- What's your favorite meal to make?
- What TV show is your guilty pleasure?
- How many days could you spend alone with no human contact?
- What's your favorite season?
- What do you do on your birthday?
- What's your favorite color?
- When you're feeling sad, what song immediately puts you in a good mood?
- Do you prefer an ocean or a lake?
- What's the craziest thing you've ever done?
- Do you believe in aliens?
- Would you ever go on a reality TV show?
- Do you consider yourself outgoing?
- If you could only eat one meal for the rest of your life, what would it be?
- What's your favorite podcast?
- What's your favorite restaurant?
- What's your hot take?
- What city do you think is underrated?
- What city do you think is overrated?
- You have 20 minutes of free time. What do you do with it?
- If given the option, would you choose to live on a remote island?
- Do you believe in ghosts?
- What historical event are you fascinated by?
- What was your favorite subject in school?
- What's your go-to order at a coffee shop?
- Are you a regular anywhere?
- If you could change your name, what would you change it to?
- What's a hobby you want to pick up?
- What's your favorite pasta shape?
- What invention had the biggest impact of the world?
- If you could go back in time for one hour, which year would you choose?
- What's the best gift you've ever received?
- What's the best gift you've ever given?
- What's your favorite movie genre?
- When you go to the movie theater, which snacks or drinks do you always buy?
- Do you have a hidden talent?
- What's your favorite fun fact?
- If you won the lottery tomorrow, what would you do?
- What is your morning routine?
- What's the last thing you do before going to sleep?
- What's your favorite type of food?
- Who is your least favorite celebrity?
- What's your favorite workout?
- What chore do you dread doing the most?
- What chore do you secretly love doing?
- What was your favorite age?
Best Questions to Ask a Romantic Partner
- What's your pet peeve in a relationship?
- How do you deal with insecurities in a relationship?
- What did you learn from your last relationship?
- What are the most important qualities you need in a partner?
- What do you think are the keys to a successful and healthy relationship?
- How important is physical intimacy to you?
- What is your love language?
- What is your attachment style?
- What's your ideal date?
- Have you ever been in love?
- What's your biggest fear in a relationship?
- What's your biggest turn on?
- What's the most attractive quality someone can have?
- Have you ever been through a bad break-up?
- What's your best pick-up line?
- What's your favorite way to show your partner you love them?
- How do you handle conflict in a relationship?
- Have you ever been cheated on?
- Have you ever cheated on someone?
- What's your biggest regret from a past relationship?
- Do you think dating apps are harmful or helpful?
- When is the right time to tell someone you love them?
- Who's your celebrity crush?
- How do you define a healthy relationship?
- What do you need in a relationship?
- What's a deal-breaker in a relationship?
- What are your views on marriage?


