21 Questions Game: Dig Deep with Fun and Flirty Questions (2024)

Want to get to know someone on a deeper level? The classic "21 Questions" game has all the right questions to help you get to know someone better, whether it's your best friend or your crush. We've rounded up the most interesting questions to spark great conversations about anything and everything. With fun questions like these, you'll literally never run out of things to talk about. (If you're looking for other fun things to keep you busy, we've got you covered with these game ideas.)

How to Play the 21 Questions Game

Playing 21 questions is super simple and straightforward. You can play with two or more people. I If you're playing with two people, you and the other person take turns answering questions. You can also modify this by having one person answer several questions in a row (or all 21 questions) before reversing roles and having the other person answer questions.

If you're playing in a group, the first player can choose a question and then the group can go around one by one and answer that question (with the person who asked the question going last). After everyone answers, the next player chooses a question and everyone answers again, and so on.

You can set rules that allow each player to skip a turn (or multiple turns) if they don't feel comfortable with the question— or you can play in hard mode and make it mandatory to answer every single question.

Now, onto the list of questions! Ahead, you'll find more than 21 questions (gotta account for those potential skips), including additional flirty questions that are perfect if you happen to be playing with a crush.

21 Questions List

1. What's the weirdest dream you've ever had?

2. If you could travel to any year in a time machine, what year would you choose and why?

3. If you could change one thing about yourself, what would it be?

4. What's one of the most fun childhood memories you have?

5. If you could have dinner with a famous person (living or dead), who would you choose?

6. What's your favorite movie to watch over and over again?

7. What's your favorite season of the year?

8. Who is your celebrity crush?

9. What's your biggest fear?

10. What's the wildest thing you've ever done?

11. What's the best advice you've ever received?

12. What's a bad habit you had that you've been able to overcome?

13. What's your dream road trip destination?

14. What's your favorite food of all time?

15. What are three items on your bucket list?

16. What's your biggest regret?

17. What's your favorite thing about yourself?

18. What's the weirdest thing in your closet?

19. If you had to guess what people appreciate you the most, what would you say?

20. What's your dream job?

21. If you could be a part of a family on any TV show, which family would you choose?

22. Of all the personal questions I could ask you, what's one you wouldn't want to answer?

21 Questions Game: Dig Deep with Fun and Flirty Questions (2024)

FAQs

What are some juicy 21 Questions? ›

Best juicy questions
  • Where is your favourite place to be kissed?
  • And where is your favourite place to kiss someone?
  • Have you ever sent a nude photograph?
  • Have you ever received a nude photograph from someone else?
  • What attracts you to someone else?
  • What do you wear to bed?
  • Have you ever had a sexy dream about someone?
Dec 15, 2023

What are some flirty 21 Questions? ›

If you're playing with your crush or on a first date, consider these flirty questions your go-to.
  • Do you believe in love at first sight?
  • What was your first kiss like?
  • What was your best kiss like?
  • What was your first impression of me?
  • What's your idea of a perfect date?
May 5, 2021

What are the flirty questions in 20 questions game? ›

Flirty Questions for Your Crush
  • Do you enjoy being single or do you want to find a serious relationship?
  • What's the craziest thing you've ever done on a first date?
  • Do you believe in love at first sight?
  • What's the weirdest thing you've ever put in your mouth?
  • What's your most R-rated guilty pleasure?

What are some spicy Q&A questions? ›

Dirty Questions to Ask Your Crush
  • What are your biggest turn-ons?
  • What's your favorite sex position?
  • How do you feel about one-night stands?
  • What are your biggest turnoffs?
  • Do you like sexting?
  • Where's the hottest place you've had sex?
  • How do you feel about PDA?
  • Have you ever had sex in public?
Apr 8, 2024

What's a good flirty question? ›

Flirty Questions To Ask a Girl
  • It keeps happening. ...
  • —Bradley, 41, Ottawa, Canada.
  • “What's the sexiest place you've ever visited?”
  • “What celebrity do you think would be best in bed?”
  • “What's one thing you want to ask me but are too nervous to?”
  • “How old were you when you first felt those, you know, feelings?”

Is 21 Questions a flirty game? ›

21 questions game flirty

Spice up your conversations with the ultimate flirty 21 questions game. Discover creative and exciting questions to get to know someone better and add some playful charm to your interactions.

What are some spicy 21 Questions to ask your crush? ›

Here are a few examples of dirty talk questions to ask:
  • Do I make you feel nervous?
  • What's the weirdest thing that's happened to you in the bedroom?
  • What was your first impression of me?
  • Have you ever played strip poker?
  • Have you ever had a dirty dream about me? ...
  • What's your cheesiest pickup line?

Is 20 questions flirting? ›

When trying to get to know someone intimately, a classic game of “20 Questions” is the perfect way to do it. The flirty questions game from your childhood can be used in today's dating world to get all the juiciest details you've ever wanted to know about your crush, and form a tight bond.

How do you have a fun flirty conversation? ›

Flirty Conversation Starters to Help Break the Ice
  1. Give a compliment on their appearance. What you mean: I want to see you naked. ...
  2. Ask if they're attached. ...
  3. Say you've been thinking about them. ...
  4. Mention things you could do together. ...
  5. Talk about dating and being single. ...
  6. Offer to be their date.
May 4, 2019

What flirty questions to ask a guy? ›

Flirty questions to ask a guy
  • What do you find most attractive about me?
  • What would our first date look like?
  • What are you like as a boyfriend?
  • What's your love language?
  • When are you going to ask me out?
  • When was the last time you felt butterflies?
  • What does love mean to you?
  • What's the worst pick-up line ever?
Dec 29, 2023

How to spice up 21 questions? ›

Flirty 21 Questions Ideas
  1. Do you believe in love at first sight?
  2. What is your dream date?
  3. What do you consider the most romantic travel destination in the world?
  4. What is your biggest fear when it comes to relationships?
  5. Romantic lunch picnic in the park or a high-class dinner and co*cktails?
  6. What's your biggest turn-on?
Apr 18, 2024

How to play 21 questions with a guy? ›

The game “21 Questions” is a great game to play if you are trying to get to know someone, whether they're a friend or romantic partner. Playing the game is super easy—you just ask someone 21 questions and they have to answer each one honestly. Unlike other question games, these questions are typically more personal.

What are some deep juicy questions? ›

Deep questions to ask friends
  • What's been on your heart and mind recently?
  • What are your current priorities in this season of your life, and why?
  • How would you like people to experience you? ...
  • If you had a whole day where you could do anything you wanted, what would you do?
  • What are you most proud of about yourself?

What is a hot text question? ›

With Hot Text questions, students can demonstrate understanding by citing evidence by clicking highlighted text in a sentence, paragraph, or extended reading. Teachers can define questions to allow a single choice or multiple choices.

How to start a spicy convo? ›

Romantic conversation starters for couples
  1. What initially made you interested in me?
  2. How did you know you were in love with me?
  3. Is there anything about our relationship that feels totally unique to us?
  4. Where do you see our relationship going?
  5. What does marriage mean to you?
  6. How do you feel about big proposals?
Feb 13, 2024

What is the juiciest question to ask? ›

Juicy questions to ask friends
  • What's the weirdest thing you've done in public?
  • What's an embarrassing thing you've done and never told anyone about?
  • What's the most bizarre text you've ever received?
  • What's the cringiest thing you've ever put up on social media?
Apr 18, 2024

What are some spicy 21 questions to ask your crush? ›

Here are a few examples of dirty talk questions to ask:
  • Do I make you feel nervous?
  • What's the weirdest thing that's happened to you in the bedroom?
  • What was your first impression of me?
  • Have you ever played strip poker?
  • Have you ever had a dirty dream about me? ...
  • What's your cheesiest pickup line?

What are some juicy truth questions? ›

Juicy truth questions
  • What's the worst thing you've ever done at work?
  • Do you have any fetishes?
  • What's something you're glad your family doesn't know about you?
  • Have you ever cheated on someone?
  • What's the worst thing you've ever done?
  • What are your thoughts on polyamory?
Dec 14, 2023

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