21 Questions Game – 41 Questions to Ask Your Crush

The game of Twenty-one Questions is pretty much like truth or dare, except there is no “dare,” and the “truth” questions are less revealing.

How to Play 21 Questions

The mechanics of 21 questions are very straightforward. One person asks a question, which is then answered by the other person as truthfully as they can.

If there are only two players, you can decide amongst yourself if one person finishes all of their 21 questions before swapping turns or if you get to alternate between asking each other your set of 21 questions.

Feel free to make your own rules. For example, you can agree at the beginning of the game if each player can use a “pass” and how many passes are allowed. The “pass” can then be your way of ditching questions you don’t feel like giving truthful answers to.

The rules are similar when playing as a group with the addition of the following variations:

One person asks the first question, answered by everyone in the group before proceeding to the next question; or

One person directs the first question to the person next to them, and then that person will ask the person next to them a different question until everyone has asked and answered 21 questions.

Most of the time, you want to ask a follow-up question after the other person answers the initial question. You can agree amongst yourself is this is counted in the 21 items or not.

Here are some of our 21 questions ideas to help you get your conversations started.

21 Questions for Your Crush

Starting a conversation is always tricky during first dates. Use these conversations to break the ice and get each other talking.

  1. If you could only eat three food items for the rest of your life, what would they be? 

Planning where to eat on dates can be a mission, especially when you’re still at the early stages of dating. Their answers to this question will help narrow down your options when it comes to dinner dates.

  1. If you were offered to be tattooed, what and where would it be? 

Tattoos usually have meaning to them. This question is sure to reveal something about the other person’s past.

  1. What is your favorite game show?

Is it Family Feud, American Ninja Warrior, Wheel of Fortune, or Jeopardy? Who knows, other than finding out if you share similar favorites, you may end up watching these game shows together.

  1. What do you usually do on weekends?

Follow this question up with something like, “should we do something different together this coming weekend?” Might be a cheesy pick-up line, but hey, if it gets you a YES, does it really matter?

  1. What is something people think or believe about you that you consider as “fake news”?

This is a spin on the “what is a common misconception about you” question. Asking this could earn you plus points as it makes the other person feel that you are interested in them and their truth over other people’s opinions about them. 

  1. If you were asked to watch a movie on repeat for a day, what would it be?

Would it be a feel-good rom-com, a tearjerker, a thrilling mystery, an action-filled plot, or a film about a zombie apocalypse? Chances are, you will end up talking about a movie you both like. And if you play your cards right, you may end up watching a similar-themed film together in the coming days.

  1. What time do you usually have your alarm set on?

Ask this one rather than the boring “what time do you usually wake up.” This tells you whether they are a morning person or not. It could also give you insight into whether they are a routine-oriented person or a spontaneous one.

  1. You are scheduled to be locked in an empty room for a month and are only allowed to bring three things with you. Except for your phone, what will your three items be?

Discover the things that are important to them and what keeps them sane with this situational question.

  1. Your communication with the outside world is restricted for an entire year. Who would you talk to first at the end of that year?

This question is a good indication of how close the other person is to their family or friends. Remember the person named in the answer, as you want to be on their good side if this progresses into the more serious dating stage.

  1. If you could pick a famous person (dead or alive) as your best friend, who would it be?

This will definitely spark an exciting conversation, which could also reveal their personality and character.

  1. If you were to shoplift something, what would it be?

You probably don’t want to be dating a shoplifter, but this is a fun way of knowing what material things the other person is most interested in.

  1. What event would you watch if you were given front row seats to the Olympics?

Don’t ask them what their favorite basketball team is – you’re not even sure if they like basketball. The Olympics is a safer choice. There would always be an Olympic event that any person would watch, even if they were the least sporty person on earth.

  1. Which movie character describes you the most?

Instead of asking the age-old annoying, “how would you describe yourself,” ask this question instead. Let’s just hope they don’t say, Hannibal.

  1. What do you consider as the worst mistake of your life?

Everyone makes mistakes. This question will show you that the other person is not perfect (no matter how hot you think they are). More importantly, it reveals a bit about how they tend to deal with challenging situations. 

  1. If you were offered a modeling stint, what brand would you like it to be from?

These days, models pose for almost everything – from tangible products to organizations or movements. Find out what they would advocate for and why. 

  1. How many photos are in your phone’s gallery right now?

This is not really about the number, but about what sort of photos constitute that number. Is it 1,000 selfies, 1,000 beautiful sceneries, 1,000 cats, or 1,000 random shots? The tendency is, they will tell you what most of the photos are without you having to ask them. 

  1. What app do you use most on your phone?

Nowadays, it is almost impossible to find someone who will tell you they only use their phones for calling. Get a feel of how they spend their screen time. Is it on social media, the news, games, finances, messaging, job searches, travel apps, or dating? That tells you a lot, doesn’t it?

  1. Imagine yourself being on the worst date ever. What makes it really bad?

Asking for their ideal date is so overused. Learn more about what they hate on a date instead, and avoid doing them!

  1. When you get extremely angry or upset, what often calms you down?

If this goes past the getting to know you stage into a serious relationship, you better know the answer to this question by heart.

  1. What is the craziest thing you’ve done for a relationship?

You can gauge how committed or how far they will go in a relationship by their answers to this question. The answer will also tell you whether they are worth pursuing or if you are better off running for your life NOW. 

  1.  Do you think you love someone because you need them, or need someone because you love them?

This question may sound a bit philosophical – but it makes for a conversation starter that can get you talking for hours, especially if you get into discussing the merits of both statements in the question.

21 Questions to Know Them Better

We have made these questions clean for use in the professional setting. We envision these questions to be asked in games at workplace seminars, meetings, team buildings, or student group exercises.

Because let’s be honest, outside the professional setting, a set of truth or dare would be more exciting, right? 

  1. What do you consider as the best thing that has happened to you in the last week?

This is a great way to start the game. It puts everyone in high spirits and sets the cheerful tone for the rest of the day.

  1. What was the last TV series you binged watched?

Don’t judge them if they say, Tiger King. They were probably just lured to it by the hype – just like the rest of us.

  1. If you weren’t working in your previous role now, what do you think you’d be?

This gives you a hint of their passions and their dreams.  If they say they’d probably be singing in a concert somewhere, ask them to sing a line or two. You might find yourself surprised by what you discover about your peers through this question.

  1. What is the most recent photo on your camera roll?

Add a bit of fun by asking the person to pass their phone around the group so everyone sees that. The reactions will either be a run of “Aaawww”s, “Eeeewww”s,…. or crickets. 

  1. If you could only celebrate one holiday for a year, what would it be?

This single question can reveal a lot about your colleague. If you listen intently, you would be able to work out whether they were in a relationship, if they have kids, if they were religious, what their personalities are – and so much more.

  1. Which superhero would you choose to run this country?

Don’t worry; this question is completely apolitical. If anything, it would probably be a DC versus Marvel debate amongst the group, which is all the more fun in itself. Who will manage our country’s finances better, Batman or Ironman? Should we let Hulk handle our diplomatic affairs? Would Robin make a good vice president?

  1. What do you see yourself doing after a very stressful day?

You may find some common ground and finally have someone to do those after-work drinks or mani-pedis with.

  1. Except for Santa Claus and other holiday characters, what lies did your parents tell you as a child that you believed in so much, but laugh about now?

Forget Santa, we all thought he was real until some point. Did they always tell the truth for fear of having long noses? Did they think they came from storks? Or did they buy the classic, the dog ate all the candy? Find out how gullible you all were as kids and laugh at them together.

  1. What is your go-to takeaway meal?

If you are working or studying a lot together, this information will be extremely handy, especially during those late-night study periods or overtime sessions. 

  1. On a scale of 1 to 10, how grumpy do you get when you don’t have your morning cup of coffee?

Again, another question whose answers will explain a lot in the mornings when they turn up to work or class snappy and unproductive. 

  1. If you were to be stranded in a country for a year, which one will it be?

Get to know what they picture their ideal life to be. Would they prefer a laidback lifestyle and be stranded by the beach? The busy streets of Tokyo, perhaps? Or would they instead be stuck with wildlife in a forest somewhere?

  1. What time of the day do you see your best self?

Some people are morning persons, while some are more productive just after lunch. Find out what side of the clock they perform best on, and use this to your team’s advantage.

  1. What emoji best describes what your feeling right now?

Ask this question midway to have a feel of how well the group is responding to the game. If almost everyone is giving out bored emojis, it may be a sign for you to cut the game short. Hopefully, poop emojis don’t pop up during this time.

  1. What is your favorite ice cream flavor?

Sometimes, questions in 21 questions are asked just for the fun of it. Just like this question, which may even lead to a friendly discussion. Are you on team vanilla or team cookies and cream?

  1. What zoo animal do you see yourself as?

Hopefully, you get a diverse mix of animals in your group and not just a roomful of lions, bears, or crocodiles.

  1. How long would you last without your phone?

Some people almost need to have their phones glued to their hands. Find out who would last the longest and who can’t survive without their gadget.

  1. Would you rather be a Kardashian or one of the casts in Tiger King?

You’re probably thinking, oh god, not another Tiger King reference. But hey, these two shows are both outrageous in their own right. Wouldn’t you like to know the group’s opinion on which of them is the lesser of two evils?

  1. If it were to be your last ever meal, would it be burger or pizza?

The classic fast-food debate. Watch how the room divides when each person answers this question. We would add fries to the mix, but then that would just make everyone agree on something, which is less fun.

  1. In your opinion, what has been the best invention in this world so far?

This is a very random question but could potentially reveal what each person is interested in and what they need or appreciate the most.

If they’re a mom of three, the robotic vacuum, dishwasher, and washing machine could well be their best friend. Environmentalist car enthusiasts may think that Tesla is heaven-sent. The millennials in the group may believe that the internet and smartphones are the Best.Inventions.Ever.

  1. What dating app do you have on your phone?

Okay, we know we said these questions are for group gatherings and not for any romantic adventures. But if you’re single and find some of the people in the group cute, this question is the easiest and the most subtle way of weeding out who is actively on the lookout. We have to make this disclaimer, though: It will not guarantee that they are not already in a relationship — if you know what we mean. 

  1. Can you say, “Thank you.” in another language other than English?

Instead of asking, do you speak another language, ask this one instead. Most likely, they will end up telling you how or why they learned the language and whether or not they speak any other ones.

Did you find a question you can use in your game? Don’t worry if you end up diving into the topics more in-depth, and the flow of questions and answers doesn’t go smoothly. Remember, this is exactly the aim of the game – to get the participants engaging in conversation.

If you want more question ideas to break the ice and start a conversation, check our Q&A article or the 225 questions to get to know someone.