21 Questions Game: The Best Questions To Ask A Guy Or Girl

Whether your relationship is in the nascent stage or you’ve been together for a long time, it’s always fun to ask your special someone interesting questions or personal questions to get to know them on a deeper level. Rather than asking your ideal partner random questions, you can turn your date night into something you can cherish. And one great way of achieving that is by playing the simple yet freaky 21 questions game.

Read on as we tell you the basic rules of the game and give you different types of interesting questions you could use or take inspiration from to draft your own questions.

In This Article

How To Play The 21 Questions Game?

As the name suggests, the 21 questions game is a challenge wherein a person asks 21 different questions that revolve around just about any topic, opinion, dislike, like, or life choice. The perfect questions that you ask depend on the relationship you share with the other person or people involved in the game and what you would like to know about them. This activity can be incorporated into a fun weekend or party game. It can be made more challenging by transforming it into a quiz, quiz bowl, or trivia game. Including think hard questions such as riddles and brainteasers adds an extra level of difficulty and engagement.

21 Questions Game Rules

There are different versions of the game, and you could come up with any interesting rule you could possibly think of. However, to play the classic version, here’s what you have to do.

  • Two or more players can play the game.
  • Choose one person from the group to answer 21 questions.
  • All players involved ask the chosen one a set of 21 questions.
  • Once the player answers all the 21 questions, you move onto the next person who then answers 21 questions, and so on.
  • Any player can volunteer to answer the next set of questions, or the person who finished answering the questions can nominate another player.

Also, keep these pointers in mind to have a fun time.

  • Do not worry if the open-ended questions lead to a discussion, as the sole objective of this question game is to get to know the other person and kick-start a conversation.
  • There are no correct answers or wrong ones. It’s more a game of asking interesting questions to get the other person out of their comfort zone and openly talk about their views, opinions, etc.
  • If you play this question game honestly and without qualms, it can be an excellent way to build a connection and get to know each other on a deeper level.

Let’s start with the absolute best questions to ask during the 21 questions game.

Best Questions To Ask During The 21 Questions Game

Here are some good 21 questions to ask your partner or friend:

  1. What is the one dream you want me to help you achieve?
  1. What is our greatest strength as a couple?

Image: Shutterstock

  1. As a couple, what new hobbies would you like to try together?
  1. What do you think will make our relationship more exciting?
  1. What is that one similarity between us that you love?
  1. What can we do to strengthen our relationship?
  1. Do you listen to your brain or heart when you make an important decision and why?
  1. What’s your favorite way to spend time with your better half?
  1. What’s the most rewarding part of your daily routine?
  1. If a genie were to grant you three wishes, what would they be?
  1. Do you believe in second chances?
  1. What are the five things on your bucket list?
  1. Do you consider yourself to be a giver or a taker in a relationship?
  1. If you could describe your relationship in one word, what would it be?
  1. What are the top few things that make you happy about your relationship?
  1. What’s the one thing about your life you would never change for someone else, including your better half?
  1. What’s the one thing you think makes your relationship unique?
  1. Would you prefer to decorate the house with many candles or a lot of roses for the perfect date night?
  1. If your partner worked in a job that consumed all their time, would you make them quit?
  1. If you could change one thing about your partner, what would it be?
  1. What’s the biggest lesson you’ve learned from your past relationships?

protip_icon Do remember
Keep an open mind, and do not judge a person for their answer. This will encourage them to open up and express themselves better.

21 Funny Questions To Ask

Image: Shutterstock

  1. What would you give up? Carbs or alcohol?
  1. If you were stranded on an island, what are the three things, and who are the three people you would take along?
  1. If you knew you wouldn’t get caught, would you become a thief?
  1. What is the craziest thing or weirdest thing you’ve eaten and felt horrible about?
  1. How many selfies do you take in a day?
  1. Describe the most awkward date night you’ve had?
  1. If I let you dress me, what would I wear for our next date night?
  1. What’s that one memory of your better half that always makes you laugh?
  1. If you could have a secret identity for a day with a free pass, what would you do?
  1. If you could trade lives with anyone for a week, who would it be and why?
  1. What is your greatest guilty pleasure?
  1. If you were a part of the circus, what kind of performer would you be?
  1. What is that one silly habit of yours that you don’t tell about to people?
  1. What are some of your silly accomplishments that you’re secretly proud of?
  1. Would you prefer a better half who is as hairy as a gorilla or completely hairless?
  1. If you could be an animal for one week, which one would you choose?
  1. What’s your favorite food to eat when you’re watching your favorite movie?
  1. Describe one of your most embarrassing moments that makes you laugh when you look back at it.
  1. Would you rather try skydiving or snorkeling?
  1. What’s the weirdest thing you have seen in someone’s closet??
  1. What are the most cheesy pickup lines someone used on you?
protip_icon Quick tip
Do not ask too personal questions, especially if you are in the beginning stage of a relationship. Keeping it fun and lighthearted will allow you and your partner to laugh away any awkwardness.

21 Dare Questions To Ask

Image: IStock

  1. I dare you to sing and dance like a crazy person for two minutes.
  1. I dare you to let your partner give you a makeover from head to toe.
  1. I dare you to become the slave of another player of your choice for seven minutes.
  1. I dare you to pick four random ingredients from the fridge, mix them, and drink it.
  1. I dare you to give your partner a back massage for ten minutes.
  1. I dare you to prank call anyone of your choice.
  1. I dare you to make everyone in this room laugh for two minutes,
  1. I dare you to send the last picture you clicked on your phone to your mom.
  1. I dare you to make a funny face, click a picture, and make it your social media profile photo for one night.
  1. I dare you to perform all your dares twice.
  1. I dare you to sing and talk for the next five minutes.
  1. I dare you to put an ice cube down your pants and let it melt.
  1. I dare you to tell me what you honestly feel about me.
  1. I dare you to like the first 20 posts on Facebook.
  1. I dare you to ring the neighbor’s doorbell and run away.
  1. I dare you to call your mom and tell her about your first kiss.
  1. I dare you to run around the house for the rest of the game with someone’s underwear on your head.
  1. I dare you to go outside and wink at the first person you see.
  1. I dare you to put your socks in your mouth.
  1. I dare you to order pizza and coke.
  1. I dare you to let one person from the group draw on your face using a permanent marker.
protip_icon Be watchful
Do not set illegal or dangerous dare tasks on both sides.

21 Questions To Ask A Guy

Image: IStock

  1. Do you prefer having a curly mustache or a long beard?
  1. If you were given a choice to pick between the air force and navy as a career choice, which would you choose?
  1. Do you still have feelings for someone from your past?
  1. Never be able to watch your favorite sport or never be able to play your favorite sport?
  1. When did you know you were falling for your girlfriend/wife?
  1. What is your dream destination for you and your partner?
  1. Do you prefer cohabitation or marriage?
  1. When you feel sad, how would you like your better half to care for you?
  1. What are the most important things that make a relationship successful?
  1. Do you prefer a long, warm hug or a passionate kiss?
  1. When you think of spending time with your true love, what’s your favorite memory that comes to mind?
  1. If you switched places with your partner for a week, what would you do/change?
  1. If you had only five minutes left with your true love, what would you do?
  1. Do you prefer staying in or going out on date night?
  1. If your partner had to move far away for some reason, would you join them?
  1. Do you think a relationship can work without lovemaking?
  1. What is one of the craziest things to do to spice things up?
  1. What are your top three biggest regrets and special moments?
  1. Have you experienced heartbreak? What happened?
  1. If you were to have a family one day, would it be the same as yours? What would you change?
  1. Are you a jealous or possessive lover?

21 Questions To Ask A Girl

Image: Shutterstock

  1. Would you choose Jennifer Aniston’s hair or Angelina Jolie’s lips?
  1. Would you rather be the president of a country or a real princess?
  1. Would you rather have an expensive, grand vacation with your true love or an expensive wedding ring?
  1. What are you most passionate about?
  1. High heels or flats on a first date?
  1. What does your partner do that makes you smile from ear to ear?
  1. Do you express your love with presents, actions, or words?
  1. Looks or intelligence?
  1. Do you believe in love at first sight?
  1. What’s the first thought that popped into your head when you saw your better half?
  1. Do you believe in soul mates?
  1. Do you like public displays of affection?
  1. What are the top three things you look for in a relationship?
  1. What’s a deal-breaker for you in a relationship?
  1. What’s your idea of a perfect date?
  1. What’s the one thing you always wanted to say to your partner but felt you couldn’t?
  1. How important are marriage, children, and family to you?
  1. Do you believe things happen because of the decisions you take, or do you believe in fate?
  1. Did you fall in love with your partner because he was the right person or because the time was right?
  1. If you saw your partner somewhere with another woman, would you think she’s a friend, a relative, or another girl he has a crush on?
  1. Do you think long-distance relationships can work? How far is too far?

Would-You-Rather Questions To Ask

  1. Would you rather have a photographic memory or a wild imagination?
  1. Would you rather spend two nights in a haunted house or one week in the wilderness?
  1. Would you rather dump your partner if things aren’t working out or wait to be dumped?
  1. Would you rather live without the Internet or without books for a year?
  1. Would you rather inherit a lot of money or work hard and have a lot of money?
  1. Would you rather have an outdoor wedding by the beach or an indoor wedding at a heritage site?
  1. Would you rather lose all your memories of your partner or never be able to look at your partner again?
  1. Would you rather spend time with your partner watching the sunrise in the mountains or sunset by the beach?
  1. Would you rather go on a date with someone who is ugly but has a beautiful personality or someone who’s beautiful but has a bad personality?
  1. Would you rather live in a house with a personal masseuse or a private chef?
  1. Would you rather travel back in time and relive all the days you’ve spent with your partner or go to the future and spend time with your grandchildren?
  1. Would you rather raise your salary so you can give your partner more money or cut down your working hours to spend time with them?
  1. Would you rather have a blue pill and become 70 years old, live with your true love, and have $50 million in your bank account or have a red pill and restart life at the age of 10 with all the knowledge you have now but no true love?
  1. Would you prefer a partner who likes to go on long drives or long walks?
  1. Would you rather have a partner who has many friends of the opposite gender or no friends at all?
  1. Would you rather visit different dream destinations with your love interest or have an unlimited bank account to only travel with your friends and not your true love?
  1. Would you rather have a partner who has no savings but splurges a lot or have a partner who saves a lot and doesn’t splurge?
  1. Would you rather live alone with your partner or live with your parents and partner?
  1. Would you rather have a partner who is an introvert or an extrovert?
  1. Would you rather be with a much younger partner or a much older partner?
  1. Would you rather have a partner who is popular in real life or someone who is popular on social media?

Frequently Asked Questions

1. What are the different strategies to win the 21 Questions Game?

Paying attention to detail, asking broad questions, and making educated guesses can help one win the game of 21 questions.

2. What are the advantages of playing the 21 Questions Game in a group setting?

Playing 21 questions with a large group of people allows one to build strong connections, improves communication skills, and encourages one to think outside the box.

3. What are some tips for making the 21 Questions Game more enjoyable?

Mixing up different questions, setting clear rules, using humor, and giving everyone a chance to ask questions can help make the game more interesting.

With this 21 questions game, you can have a fun date night with your special person, get to know them better, and foster your bond. These questions are fun and interesting and will keep you both hooked on the conversation for hours. Come up with your own questions along with the ones listed above to add more intimacy and fun to the game. However, ensure the questions you ask are respectful and don’t make them uncomfortable. Also, ensure you go through the basic rules before playing the game.

Infographic: Dare Questions To Ask In The 21 Questions Game

Dare questions are great for bringing a person’s bold and fun side to the fore and creating gripping conversations. We bring you some enjoyable and deep dare questions to ask someone to know a person better. Before posing these questions, consider the rapport you share with them.

dare questions to ask (infographic)

Illustration: Momjunction Design Team

Get high-quality PDF version by clicking below.

Download Infographic in PDF version Download Infographic
Download Infographic in PDF version

Do you want to deepen the bond of love with your boyfriend? Ignite the flame of romance with this video featuring 21 questions to ask your boyfriend when texting! Get ready to spark some romance!

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