21 questions game: 140+ fun and flirty questions to ask

Want the inside scoop on a new crush, colleague or the newest member of your group chat? Enter the 21 Questions game.

It’s simple: take turns asking each other questions to get to know one another better. Keep it light and fun, or turn up the heat with juicier questions - the choice is yours.

To get you started, we’ve rounded up our favourite 21 Questions prompts. Now all that’s left is finding someone brave enough to play…

The 21 questions game is organised fun at its finest: it's easy to play, requires no preparation, and there's literally no rules to learn. All you need is someone (or several someones) to play with, and a list of questions to ask... more on that in a minute. One thing you might want to keep in mind though, is where you're asking the questions. A crowded pub might not be the best place to ask private questions, especially if they're on the saucy side!

That being said there are a few ways you can play 21 questions:

• Classic two people: If it's just two of you playing, it's usually fun to take it in turns, with one person asking a question, and the other answering. The person who answered can then ask the next question and so forth until you've asked 21 questions in total. With this version you can also both answer the same question before moving onto the next, or choose your own questions as you see fit.
• Classic group: If playing with more than two people, someone from the group will be selected at random and then the group will ask that individual 21 questions in a row. The next person to go can be randomly selected again.
• Ricochet: In a group setting, Person A must ask a question to any player in the group who becomes Person B. Once Person B has responded they must then ask Person C a different question, once they've answered they'll ask Person D a new question. The game continues until everyone has answered a question. You then go round again until the group has answered 21 questions.
• Round and round: Again this is played in a group. Person A asks the group a question and everyone in the group answers (usually in a circle formation) before moving onto the next question, until you get to 21 questions.

Best questions to ask

1. What movie never fails to make you cry?
2. How would your best friends describe you?
3. How far would you make it in a horror movie?
4. Who in your family are you closest to?
5. How would you describe yourself in three words?
6. If you had the option to press a button and restart your life, would you press it?
7. What is the most worn item in your wardrobe?
8. If you could move to another country for free which would you pick?
9. What food or snack that other people love do you think is overrated?
10. Which family member are you closest to? And why?
11. When you were a child, what did you want to be when you grew up?
12. What is your worst habit?
13. What was your first job?
14. What's your biggest regret from school?
15. What's your most memorable dream or nightmare?
16. Do you believe in an afterlife?
17. What would be your dream job?
18. What's the most used emoji on your phone?
19. If you could swap lives with anyone, who would it be?
20. Where do you feel most yourself?
21. Which mythical creature do you relate to on a spiritual level?
22. If you weren't in your current role, what job would you like to be in?
23. What inspires you most?
24. What would you do if you were Prime Minister for the day?
25. What are people always surprised to learn about you?
26. What moment in your past do you wish you could experience again for the first time?
27. Who would you trust to help you bury a body?
28. Do you believe in aliens?
29. When did you last cry?
30. What’s one dish you can make from scratch without a recipe?
31. Which social media app do you use the most?
32. How often do you speak to your family?
    
33. Where do you feel most at home?
34. What do you think of marriage?

Best questions to ask your crush

1. What makes a perfect date for you?
2. What gives you the ick?
3. What was your first impression of me?
4. What was your first kiss like?
5. What's your wildest dating story?
6. Do you go on many dates?
7. Who's your favourite celeb couple?
8. How do you feel about astrology?
9. Do you believe in soulmates?
10. How important are looks to you?
11. Which reality TV show would you go on?
12. How would you impress someone on a date?
13. Do you think dating apps are a good way to meet someone?
14. What's your most embarrassing moment?
15. Who do you trust the most?
16. What's your favourite thing about me?
17. What's your go to takeaway order?
18. If you could swap bodies with anyone who would it be?
19. What movie series or TV series is perfect for a cosy Sunday?
20. What's the most admirable trait a person can have?
21. What's your cheesiest pick up line?
22. What was your first impression of me?
23. What do you think my first impression of you was?
24. What’s your toxic trait?
25. Who is your celebrity crush?
26. What motivates you?
27. Do you have any weird secret habits?
    
28. Who would be your dream celebrity to date?
29. What's your guilty pleasure?
30. What would be your last meal before heading to a desert island?s
31. What's your least favourite thing about me?
32. How has your impression of me changed since we first met?
33. Which of my friends do you like the best?

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Best 21 questions to ask in a new relationship

1. What's your love language?
2. How did your last relationship end?
3. What do you value most in a partner?
4. Which city is at the top of your travel list?
5. What can I do that will always cheer you up?
6. Have you ever been cheated on?
7. Have you ever cheated on someone?
8. What would be the dream date I could take you on?
9. What are three key personality traits in a partner for you?
10. How do you deal with conflict in a relationship?
11. What's a deal breaker in a relationship for you?
12. What's something people misunderstand about you?
13. Do you believe in monogamy?
14. How do you feel about polyamory?
15. Would you like to get married one day?
16. Do you see yourself having kids in the future?
17. What are you most focussed on right now?
18. What's the biggest lesson you learnt from your previous relationships?
19. Who was your celebrity crush when you were younger?
20. Do you enjoying cooking?
21. What's your worst household habit?
22. Are you an early bird or a night owl?
23. Do you have any insecurities?
24. What excites you?
25. What frustrates you?
26. What would you like to change about the world?
27. What do you foresee being the biggest challenge in our relationship?
    
28. Are you an introvert or extrovert?
29. What's your ideal way to spend a Sunday?
30. Which of your friends do you think you're the most like?
31. Do you have a 'The One That Got Away'?
32. Has a chat-up line ever worked on you? What was it?

Best juicy questions for the 21 questions game

1. Where is your favourite place to be kissed?
2. And where is your favourite place to kiss someone?
3. Have you ever sent a nude photograph?
4. Have you ever received a nude photograph from someone else?
5. What attracts you to someone else?
6. What do you wear to bed?
7. Have you ever had a sexy dream about someone?
8. If you could sleep with a celebrity, who would it be?
9. Have you used handcuffs before?
10. Have you ever given or received a love bite?
11. Have you ever faked an orgasm?
12. What's your favourite sexual position?
13. Have you joined the 'mile high' club?
14. Have you ever skinny dipped?
15. Have you had a friends with benefits before?
16. What's your favourite sex toy?
17. Have you ever fulfilled a sexual fantasy?
18. How many people have you had sex with?
19. What makes you feel intimate with someone?
20. Do you have any fetishes?
21. How do you feel about shower sex?
22. How high is your sex drive?
23. What's your favourite part of foreplay?
24. When and where do you like to have sex?
25. Have you had a situationship before?
26. How often do you think a couple should be having sex?
27. How do you get over a breakup?
    
28. Where's the 'weirdest' place you've had sex?
29. How do you feel about sex outside?
30. Would you be open to having sex with more than one person at once?

Best deep questions for the 21 questions game

1. What keeps you up at night?
2. What do you think happens after death?
3. What's your biggest regret?
4. If you could go back and change your biggest mistake, would you?
5. Do you believe in 'The One'?
6. What's the worst lie you've ever told?
7. What's your biggest fear?
8. Who would you call if you were in trouble?
9. What's the best advice you've ever received?
10. Who do you go to when you need help or advice?
11. If you were to walk into a room of everyone you knew, who would be the first person you look for?
12. What song do you want played at your funeral?
13. Do you think your values align with your siblings?

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