21 Questions To Ask Any Person And In Any Situation!

If you genuinely want to know someone playfully, here are 21 questions to ask. Use them wisely and get to comprehend people you find amusing.

The game of 21 questions is among the most popular games for all generations. It’s a genuinely great way to find out embarrassing, funny, or interesting stories about your friends despite awkward subjects.

However, it can also be useful in everyday life. If you know what to ask, it’s incredible how much people are ready to share.

So, let’s start with something romantic, in the form of 21 questions to ask your new love interest!

21 questions to ask your crush

You met someone interesting, but your brain and your tongue refuse to cooperate. To get someone interested in you, you should be rather interesting yourself.

Be confident, let them reply, and don’t just ask one question after another. Develop a conversation by using some of the questions:

What’s one thing you’d like people to know about you without even meeting you?

If you could change one personality trait, what would it be?

Do you have any embarrassing childhood secrets, and would you like to share?

How would you name the movie about your life?

Have you ever considered quitting your job, moving to Hawai, and becoming a bar owner?

What does fun look like to you?

Would you like to be immortal, knowing that no one else around you will?

What are you most afraid of?

Who’s your superhero in everyday life?

Name a movie you could watch over and over and never get tired of?

If you could go back in time, where would you go and what year would you choose?

What is something you are obsessed with?

Do you have any useless talent?

Which historical figure would you trade places with and why?

Can you tell me about the dumbest thing you’ve ever done?

What is your earliest memory?

How would you like to be remembered?

If this was to be our last conversation ever, is there anything you’d want to say to me?

Did you find a love of your life or you’re still looking for the one?

What’s the most common assumption made about you that’s completely false?

What gives you hope and what’s the last time you felt like everything’s going to be alright?

21 questions to ask your boyfriend and girlfriend

Make a night out of playing 21 questions only with your partner. The only rules should be not talking about exes, as well as getting angry at each other.

What’s one thing you’re too hard on yourself for?

What movie was so sad that you would never watch it again?

What do you most look forward to regarding getting older?

What’s your biggest sexual fantasy, and can I help it come true?

If you could describe our relationship with a song, what song would it be?

How do you feel about sex toys?

If you could change one thing about me, what would you change?

How would you describe your package?

Could you pick one public place where you would want to have sex?

Would you make me breakfast while wearing an apron and nothing else?

Do you remember your first time, and how was it?

Would you let me do stuff to you while you were driving?

If you could see me in any clothing item, what would it be?

Have you ever boasted to your friends about us?

Do you like it when I send you dirty pictures?

Does being sneaky give you a thrill?

How do you react when watching a movie with your parents, and a sex scene appears?

When we wake, what’s the first thought that comes to mind when you look at me?

How do you feel about dirty talk over the phone, sexting, or Facetime?

If we were in a theater and I wanted to have sex, what would you do?

If I could take you on a date anyplace, where would you want to go, and why?

21 questions to ask your coworker/study partner

Whether you’re taking a break or having a coffee after work/classes, getting to know people you work with is essential for your professional achievements.

When you’re talking with people you work with, you should be avoiding questions regarding money, intimacy, and other coworkers. Keep it light, show your curiosity, you might find a friend for life.

What’s the worst job you’ve ever had, and what did you learn from it?

What gives you energy while you’re at work or studying?

If you could become an expert in something overnight, what would it be?

What advice would you give to your younger self?

What did you want to be when you grew up when you were a child?

What’s one song you have completely memorized?

What’s the weirdest food you’ve ever eaten?

Pineapple on pizza, does it get yay or nay and why since it’s so popular?

How would you describe your job to a bunch of five-year-old kids?

If you could get a new skill in 10 minutes, what would it be?

Would you rather be invisible or be able to read minds?

Would you share a personal fact no one would ever guess about you?

What would you do with your “5 minutes” of fame?

If you could only take one item on a deserted island, what would it be?

What is the oldest thing in your refrigerator and since when has it been there?

Do you have any unusual phobias and if so, can you guess mine?

What is one thing that all of your love interests have had in common?

Have you ever met anyone famous, and if so, were they naughty or nice?

What’s your least favorite thing to do around the house, yet you can’t escape it?

Which of your five senses is the strongest and how about the weakest?

If you could be on any reality TV show about dating, which one would it be?

Hilarious questions to ask anytime/anyplace

If you’re looking for neutral icebreakers to get the conversation moving, there are 21 questions to ask.

You can always count on humor to make unpleasant situations better. Let’s start our journey into innovative and funny ways to make the other person start talking since that’ our goal. To make people more comfortable, and talkative!

What conspiracy theory would you like to start if you had the power?

What’s the best Wifi name you’ve seen and which one is the worst?

What’s the most absurd fact you know?

What kind of secret society would you like to start, and what would you call it?

What’s the weirdest thing a visitor has done at your home?

Which would be the worst names to give to your kids?

What items would you buy that would make the cashier feel scared or ashamed?

Do you know some fun ways to answer questions like “how’s it going” or “what do you do”?

How often do you feel as if your brain’s on autopilot?

The most boring activity, imaginable, is…?

What piece of your body would you replace with an upgraded artificial version?

Is there something you hate for no good reason, still you can’t stand it?

What was the last thing that made you cringe?

If you could morph two animals to make one super animal, what two would you choose, and why?

If you could pick one musician to marry but could never listen to their music again, who would you choose?

What’s your weirdest “wrong number story”?

What part of a kid’s movie completely scarred you despite being completely enjoyable for everyone else?

Would you rather be a unicorn or leprechaun for a day? What is the first thing you would do?

You got a gift, and it’s an elephant. Since you can’t give it away or sell it, what would you do with the elephant?

What’s the weirdest Wikipedia page you ever found?

If you had one day to do whatever comes to mind without any repercussions, what would you do?

Developing communicational skills will not just expand your circle of friends, but also it will give you a chance to mingle with people outside your group.

Hopefully, you’ll manage to memorize our groups of 21 questions to ask. The list will allow you to become better in small talk and even turn a chit chat into storytelling.

You don’t have to be a friend with everyone, but understanding people will make you more openminded.

Therefore, you’ll become a better person.