Level Up Your Flirting Game With These “20 Questions” Ideas (2024)

When trying to get to know someone intimately, a classic game of “20 Questions” is the perfect way to do it. Not only can the inquisitive childhood game be used to get all the juiciest details you’ve ever wanted to know about your crush, but asking personal questions can help establish a tight bond as well. So if you’re looking for a fun way to reveal the object of your desire’s wants, dreams, turn ons, and quirky habits, these flirty, funny, deep, and thought-provoking “20 Questions” queries have got you covered.

Whether you’ve had eyes for a special someone for a long time, or finally want to shoot your shot with your coffee shop crush, you can take that next step just by getting to know them better. A simple game of “20 Questions” can be one-sided, or you and your crush can take turns asking each other the same questions, either popcorn style or each person asking the other the 20 questions straight through. You can set your own rules for allowing players to skip turns (or multiple) if someone doesn’t feel comfortable answering a question — like a forfeit or a simple “pass.”

The next time you meet up with your crush, make sure to keep these “20 Questions” inquiries on hand, so you’ll never run out of things to talk about.

“Get To Know You” Questions

1. What is your favorite dish?
2. Do you like to travel?
3. Do you have a dream travel destination?
4. Do you have any hobbies?

Silly Questions

1. What is the wildest dream you’ve ever had?
2. What was your best Halloween costume?

Questions About Lifestyle

1. What do you like to do in your free time?
2. What does an average weekend look like for you?
3. Besides your home, where do you hang out the most?

Personal Questions

1. What do you do when you’re home alone?
2. Have you ever kept a diary?
3. Have you ever lost someone close to you?
4. What’s your motto in life?
5. What is your biggest secret?

Funny Questions

1. What’s a weird, totally useless talent you have?
2. How would you react if your browser history was released?
3. If you could be an animal for a day, what would you be?
4. What are your three most frequently used emojis?

Questions About Stories

1. What’s the silliest lie you’ve ever told?
2. What’s the funniest excuse you’ve ever made to get out of a bad date?
3. What’s the most embarrassing thing you’ve ever done in front of a crush?
4. What’s the wildest thing you’ve ever done?
5. What’s the worst birthday you’ve ever had?
6. What’s one story that perfectly sums up who you are as a person?

Revealing Questions

1. What’s an irrational fear that you have?
2. On a scale of one to 10, how spontaneous are you?
3. Do you judge a book by its cover?
4. What makes you cringe the most?
5. What is something you’ve always wanted to do?
6. Who is your biggest role model?

Self-Love Questions

1. What is one attribute you have that you used to hate, but you’ve grown to love?
2. What is your favorite quality?

Pop Culture Questions

1. If a movie was made based on your life, which actor would play you?
2. If you could live in one movie franchise world, which would you choose?
3. If you got to spend a day with your favorite celebrity, what would you do?
4. If you could be a member of any fictional family, which would you choose?
5. Which celebrity would you hook up with if you had the chance?

Questions About Art

1. Who is your favorite musical artist or band?
2. What are your three favorite albums of all time?
3. What’s your favorite movie?

“Would You Rather” Questions

1. Would you rather fight 500 ostriches or one T-rex?
2. Would you rather have all your dreams live-streamed on Instagram or have your most embarrassing moments go viral on TikTok?
3. Would you rather your loved ones always be truthful with you or tell you lies to protect your feelings?

Deep Questions

1. If you could find out how you would die, would you want to know?
2. What’s your philosophy in life?
3. What are you most grateful for?
4. If you had the ability to change one thing about your past, would you take it?
5. Why are we here?

Flirty Questions

1. What was your first kiss like?
2. What do you like most about me?
3. What are your thoughts on sexting?
4. What turns you on?
5. What’s a sex scene from a show or movie you’d love to recreate?

Interesting Questions

1. What do you think your sun, moon, and rising signs say about you?
2. If you could have dinner with anyone living or dead, who would you dine with?
3. What are your thoughts on work-life balance?
4. If you could live in another era, which would it be?

Hypothetical Questions

1. If you could be any mythical creature, what would you be?
2. Who in your friend group would last the shortest in a zombie apocalypse?
3. If a genie offered you three wishes, what would you wish for?
4. What would be the title of your comedy special?

Questions About Love

1. Have you ever been in love?
2. Have you ever gotten your heart broken?
3. Have you ever broken someone’s heart?
4. What’s the most over-the-top thing you’ve ever done for love?

Questions About Beliefs

1. Do you believe in ghosts?
2. Do you believe in soulmates?
3. Would you consider yourself religious or spiritual?
4. Do you believe in second chances?
5. What do you think is the meaning of life?

Thought-Provoking Questions

1. What does support look like to you?
2. What is your communication style?
3. What’s your biggest regret in life?

“This Or That” Questions

1. Which do you value more: honesty or loyalty?
2. Which is more important to you: money or work?
3. Which is more important to you: platonic friendships or romantic relationships?
4. What are you more attracted to: personality or looks?
5. Where would we go on our first date: movies or restaurant?
6. Which is more important to you: career or love?

Questions About The Past

1. Is there someone from your past that you still think about often?
2. Have you ever disappointed someone?
3. How have you changed in the last 10 years?
4. What did you want to be when you were a kid?
5. What were you like in high school?

Questions About The Future

1. Where do you see yourself in 10 years?
2. What do you think the future will look like?
3. Do you want kids?

Questions About Dating

1. What was the best first date you’ve ever been on?
2. What was the worst first dat you’ve ever been on?
3. What is your biggest dating ick?
4. What’s your idea of a perfect date?
5. If you came across my profile on Tinder, would you swipe right or left?

Questions About Relationships

1. What’s a relationship dealbreaker for you?
2. Are you friends with your exes?
3. What qualities are you looking for in a partner?
4. In your opinion, what are the makings of a healthy relationship?

Introspective Questions

1. What would you consider to be your best quality?
2. What’s the greatest challenge you’ve ever had to overcome?
3. What’s the greatest lesson you’ve learned so far in your life?
4. What drives you the most?

Questions About Friends

1. How would your friends describe you to someone else?
2. What is a quality you value in a friend?
3. What would your best friend say is your worst quality?
4. How long do you typically wait to introduce your partner to your friends?

Questions About Family

1. Who is the person you’re closest to?
2. You and another person of your choosing are the last people on Earth. Who are you living out your last days with?
3. Are you close with your family?
4. Who’s someone you can always count on to answer your calls?

Goal-Oriented Questions

1. What is your biggest achievement in life so far?
2. Do you have any major life goals?
3. What do you hope to accomplish in life?

Questions About Love Languages

1. What is you love language?
2. What is the best gift you’ve ever received?
3. What’s the best compliment you’ve ever received?
4. What does quality time look like to you?

Emotional Questions

1. When was the last time you cried?
2. What’s a movie that always makes you cry?
3. Are you more emotional or rational?

Random Questions

1. If you had one day to do whatever you wanted, what would you do?
2. What is your favorite time of year?
3. How many times have you moved throughout your life?
4. What is one talent you wish you had?

This article was originally published on April 4, 2022