200 Juicy & Funny Deep Questions to Get to Know Someone Better

The way to sail through your first meeting with anyone is to be respectful yet confident. Here are some questions to help you connect with someone.

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The number of times we have heard our friends’ awful first date stories are too many. Granted, first dates are always nerve-wracking but I have found that asking questions about the other person is the key to smooth sailing. Boys and girls, it does not mean that you should not talk about yourself because that is a very important aspect too.

This little trick up my sleeve is versatile. I use it for people with whom I feel a spark of friendship or even to forge professional ties. I learned it from my best friend who asked me a combination of intriguing, hilarious, and often insightful questions.

Tips to Ask Questions in Right Way

When you are on your journey to know someone, you have to remember that asking questions is an art. You want the other person to feel comfortable, not like they are in a rapid-fire round.

  • Before you start, seek their permission to ask questions. We guarantee that they would admire you more for your politeness.
  • Take prominent pauses between asking the questions. It will help it look like you are not reciting off of a list.
  • Use soft and non-intrusive words in your question.
  • Your questions musn’t be probing them for deeply personal or embarrassing information.

Casual Getting To Know You Questions

I love these questions because they can be utilized in any scenario. When you are armed with these, you can conquer a date, professional pow wow, or just a friendly hangout.

1. Where are you from?

It is a simple opening question. It is not too threatening yet it will provide you with a key detail. As it is a common question, the next person would not feel like you are intruding.

2. Do you happen to have a pet?

If the person answers yes, you are in the sweet spot. People love to talk about their pets. Once pet parents start talking, there is no stopping them. It is good news for you as you will get to know them better.

3. What are you currently doing work-wise?

You can ask this question on a date, in a professional setting, etc. As most people do some sort of job or run their business, you are in luck. If the person answers that they are not currently working, you can apologize and move on.

4. Where would you say you will be in, five years?

For some people, it is a difficult question. You can give them time to answer. The answer will tell you a lot about how the person sees their future what are their goals and how they see themselves in the future. It will tell you whether your future and theirs align or not.

5. How have you been doing recently?

Trust me, this question will catch many off-guard. It is the simplest question but the sweetest. Often, people do not get asked how they have been. It will show them that you care about their well-being.

6. What do you like to do in your spare time?

This is to get to the interesting part of them. You will gain insight into how they live their life. It will also give you intel for future date or hangout ideas.

7. How have you been liking this (place) so far?

With a breezy question like this, you will relax them. It will bring the conversation to the present. Moreover, you will get to know what they think about the restaurant, cafe, etc.

8. Do you believe in cat or dog supremacy?

The age-old debate of cats versus dogs is a good place to start. People who do not have a pet have an opinion on this too. if you are planning on dating this person and have a cat/dog, this is the perfect question.

9. Have you ever tried your hand at a musical instrument?

Get to know if the person sitting next to you has a bit of music magic in them or not. If they do, they could always play for you in the future.

10. Would you call yourself an introvert or extrovert?

Introverts and extroverts lie on the opposite ends of the spectrum. Both have their own needs and preferences so ask what the other person is like. The future activities that you guys do together depend on this answer.

11. Are you a morning person or a night owl?

So many of us are guilty of being the night owl. If you both are the same, daily conversations would become that much easier. Even if you are not, you can make it work.

12. If you were not at your current job, what do you think you would be doing?

Many people are stuck doing jobs that they do not enjoy. Ask them if they are happy with their work. If not, get to know what would they rather be doing. The answer might be fun and it will definitely help you know them better.

13. Who is your favorite music artist?

This is where it can get a little dicey between the two of you so tread lightly. I have seen many people be defensive of their favorite singers. If you do not enjoy their music, express your dislike mildly. Respect their choice and be happy for them.

14. Do you think that you have peaked in your life?

This particular nugget always gets sparkling answers. It tends to put their other person in the limelight. The key is to show them that you are not going to judge them no matter their answer.

15. What is your go-to place to relax?

This is such an important question to ask your date or potential friend. If you are planning on having any kind of relationship with them, you need to know this. When you do, you can hang out at the place together and form a bond.

16. Are you interested in dancing?

Dancing makes life brighter. If they are light on their toes, invite them out on the dance floor. Maybe even tease them with a little dance-off. The bottom line is that the answer will help your dating life.

17. How did you happen to come here today?

If you just bumped into them, you have to ask them this question. It will tell you a lot: the reason they are there, where they were before, etc.

18. What does your usual day look like?

If you want to get to know someone, you have to know all of them. The big sparkly parts are prominent but what about their normal? A usual day of a person tells a lot about them. After all, if you are planning to be in their life, you would aim to be a part of their usual day.

19. Do you think that money really cannot buy happiness?

Personally, I find this concept nonsense. I have always seen that money buys happiness. If they believe otherwise, ask them their reason. Maybe they have a different perspective and experiences to go along with it.

20. Do you like tea or coffee?

Are you an avid coffee drinker? Do you believe in coffee supremacy as I do? If so, get your answer right now. You should know whether you are getting together with a tea or coffee drinker.

21. Do you have a pet peeve? If so, what is it?

A healthy relationship is one where both people are aware of each other’s pet peeves. Once you get to know theirs, let them know yours too. This information should be out of the way as early as possible.

22. How would you define success?

For some people, the definition of success having multiple houses and cars. Yet I have seen people who think success is when you are at peace. The answer of the other person will tell you of their values.

23. What do you think about the (current global event)?

Whichever current global event has your interest, ask their opinion about it. Get in their head to see what they think about it.

24. What is your favorite movie or TV series?

I love seeing how animated people get talking about their favorite movie or drama series. Armed with this knowledge, you would be able to plan movie nights perfectly in the future.

25. What is your comfort food?

Comfort food is soul food. It helps a person through tough times. Ask them what helps them feel safe and comforted. It might even give you ideas about new comfort foods.

Deep Personal Getting To Know You Questions

We know the casual questions to ask someone but is that enough? How do you get to the core of someone? These questions are ideal for it but make sure that they are receptive to them. It is better not to divulge these when you are meeting your boss or clients.

1. What has been the pinnacle of your life?

Someone that feels close to you will be willing to give you this answer. In revealing their most successful time, they will be sharing a part of themselves. It will let you know how they see themselves.

2. Would you say that you are happy where you are in your life?

They might not be happy with their life at that point. You should come in at that point to tell them that it is going to be okay.

3. Who are you the closest to in your life?

The hierarchy of relationships can be difficult to decipher but it is an important one. If they allow you, you can also make efforts to form a bond with their close someone.

4. Would you like to share with me about the lowest point of your existence?

This is a very sensitive question and should be treated as such. If they seem a bit down already, do not ask them this question.

5. What is something that nobody knows about you?

It could be a dark secret or an embarrassing tidbit. They could even let you in and be vulnerable with you.

6. Have you ever had the misfortune of having your heart broken?

Ah, heartbreak. I have gone through it one time a many. What made it feel a bit better was when someone would ask me about it. If you are genuine, the next person would open up.

7. Have you ever lost someone close to your heart?

If you feel that you are close to them, this is an appropriate question. They could name a person or pet. What you need to do is be respectful and a source of comfort.

8. Have you ever been in love?

We all love “love” and bet that they would like to dish about theirs as well. They might be a bit shy at first but use your charms. Get to know what is in their heart.

9. Do you have a crush on anyone at the moment?

Having a crush might sound a bit like high school but all of our crushes at all ages. Asking this on a date is a bit risky. The worst-case scenario is it makes you look dumb or arrogant. The best-case scenario is that you come off as confident.

10. How do you cope with grief?

It is a good instinct in dating or being friends to know someone’s coping mechanism. With this awareness, you can help them by participating in their ways (if appropriate).

11. What is the best memory of your life?

The best memory can be from any moment of their life. It could literally be a moment or spread over days. When you ask them about it, you indirectly experience it too.

12. What is the one thing that you have done that you are ashamed of?

Shame sharing is not always easy. They might balk but approach it with care. Show that you mean no harm.

13. What is the worst memory that you have?

It is true that knowing it will get you to know the person deeply. You just need to remember that it could be very triggering for them. You ought to be prepared to be there for them.

14. Have you ever shoplifted anything?

Shoplifting is not in everyone’s record. If it is in theirs, it is a spicy little nugget. Juvenile shoplifting is pretty common in many countries. If they shoplift as an adult, it is a red flag.

15. In a life or death situation, would you save yourself or someone that you love?

If the answer is themselves then it means that they love themselves the most. Frankly, we do not see any harm in it.

16. Do you consider yourself to be an honest human?

Honesty is a very subjective thing. Ask them what their definition is. It will tell you a lot about their ethics.

17. Would you ever betray the person you love the most for one million dollars?

This is one of my favorite questions. If they answer yes, it means that they love money more.

18. What is your favorite childhood memory?

Find out if their beloved childhood memory involves spending time with grandma. It could be going on some trip. The possibilities are endless.

19. Have you ever been unfaithful to your partner?

It is a tough question. They might probably refuse to answer them. However, if you are looking to date them, this information is essential for you.

20. What is your worst fear?

Fears can often be irrational. You want to know them so that you do not do anything to ever trigger them.

21. What is the best life in your opinion?

Everyone has their version of the best life. It could be having all the world riches, being surrounded by love ones, or eating and never gaining weight.

22. Do you have any regrets up till now?

A life with no regrets is a life not lived fully. Find out if that is the situation with them.

23. What gives you the most satisfaction?

Let’s see if their answer revolves around themselves, an activity, or other people. You can always tell them your answer too. It will help to clarify where you both stand.

24. Have you ever experimented with drugs?

It is okay to experiment with legalized and healthy drugs. Nobody should be judged for it as long as they are not harming anyone.

25. What is your biggest failure ever?

The way they tackle their failures will tell you a story of their strength. It will give you an idea about their tenacity.

Question to Understand Someone’s Psychology and Beliefs

The most successful relationships are ones where the core essential beliefs of one party do not offend the other person. With the below questions, you will be able to understand the essence of the person you are looking to create a bond with.

1. What are your thoughts on religion?

We believe in respecting everyone’s religion. It is only polite to understand their faith and principles.

2. Are you a feminist?

Feminism is not about providing extra rights to women. It is about equal rights. Ask this question and judge whether you would want the person in your life or not.

3. Do you believe in astral projection?

This particular belief is often centered on a person’s spiritual beliefs. It is important to remember that religion and spirituality are not the same things.

4. Does your family have a history of mental health issues?

It is insanely direct and should only be asked if you know the person very well. If you mishandle it, the individual would have every right to be cross with you.

5. Have you ever had sleep paralysis?

Sleep paralysis is a terrifying experience and many go through it. It isn’t bad but can be disorienting for anyone who has been through it.

6. Do you believe in life after death?

Many people don’t think about it since it seems grim. With this question, you can open a channel for a very stimulating conversation.

7. Are you a rightist, leftist, or centrist, politically?

In today’s world of injustice, it is imperative to know people’s political outlook. It is how they live their lives. It defines what they stand for.

8. What is your opinion on climate change?

There is no denying climate change. Would you not want to be with someone who is green? Use this question to find out if they care.

9. Do you believe in the death penalty for any kind of criminals?

There is no right answer to it. It will tell you how humanistic this particular individual is.

10. How supportive are you of ethical treatment of animals?

People who treat animals right are a gem. Ask them if they care about life beyond their species.

11. Do you believe in opting for therapy or counseling?

Get to know if they believe in psychology as a subject. Furthermore, if they believe in the management of self and traumas to grow as a person.

12. What do you think about women asking for an equal wage?

Wage disparity is a serious issue in the world. A decent human would reply that men and women should be paid equally for the same job.

13. Do you support anti-abortion laws?

In the most progressive countries, there are still anti-abortion laws. Find out if the person next to you support people’s right to decide on their own body or not.

14. Would you like to live in a world run by socialists or capitalists?

We already live in a capitalist world and it is grim. It should be fun to see whether they support a cause like socialism or not.

15. What are your thoughts on LGBTQ+?

In my personal opinion, it is only human to be an ally to the community of LGBTQ+. People who are against it are ones you need to be wary of.

16. Do you believe in the narrative that the human race is destroying the planet?

Centuries’ worth of evidence has shown that humans are selfish. Some people do not believe that because they think that the world only belongs to the human species.

17. Would you ever turn to drugs or alcohol to drown your sorrows?

Suc a pitfall can come in anyone’s life. It also tells about a person’s inclination towards unhealthy coping mechanisms. Find out if your person is susceptible or not.

18. Do you give any weightage to pseudosciences like astrology, homeopathy, etc.?

Pseudosciences ars scoffed at but they are always fun to talk about. If they are a believer, ask them their star sign.

19. What is your belief regarding the supernatural world?

Observe whether their belief in the supernatural comes from religion, movies, or their community.

20. Are you a believer in karma?

Karma can surely mess up a person’s life. Many don’t see it that way because they don’t believe it.

21. How necessary are wars in your opinion?

A person who supports war is okay with people being used as pawns and losing their lives for a bunch of power-hungry individuals.

22. What would you like to say about veganism?

If your person is vegan, they don’t see animals as a lower life form.

23. Is there any sense to nihilism?

Nihilism might be an extreme view for some. It should be fun for you to get to know how they feel about it, even if they are not a supporter of it.

24. Have you ever battled addiction of any kind?

If they do say yes, be kind. Addiction is taxing on the addict. You can further ask them how they dealt with it.

25. What do you think refugee laws should be like over the world?

Inquire if they feel that refugee laws should be lax and humanistic around the globe. It will tell you whether they consider all lives o be equal or not.

Getting to Know You Questions for Him

We now come to our section that is only for people that are looking to have a list of questions for dates. It can indeed be hard to get men to open up. These questions will help you with the vetting process.

1. Are you into sports?

Guys absolutely will go bonkers if you show interest in their sports.

2. Which team is your favorite?

The follow-up question will be to get to know about his favorite sports team. Ask him how long has he been a fan of the team.

3. What do you like to do on all-guys hangout?

Probe whether he likes to do the typical bro stuff on his hangouts like play video games, talk about cars, etc.

4. Are you any good at the grill?

For so many men, being a grill master is everything. Check out if he fans the flames of masculinity at a grill.

5. Would you call yourself a sensitive guy?

My experience is that most guys get confused at this question. They want to show that they are caring but also don’t want to seem “too feminine”.

6. Which is your favorite car?

You will see his eyes light up when you ask this question. Be prepared to hear about the specifics of his favorite car, it could go on for a while.

7. Are you by any chance a gamer?

There is a considerable population of guys who call themselves gamers. See if your date spends his hours on video games.

8. Which video game can you spend hours playing?

Ask a gamer about the best video game for him and you will make his life. He will give you a play-by-play of his favorite parts in the game.

9. Do you believe in normative “masculinity”?

Normative masculinity is pretty punitive. For your own good, follow it up with questions to get to know if he believes in feminism.

10. Do you like to go fishing?

Fishing seems to be engineered into men’s DNA. If you are lucky, he will tell you about his favorite fishing memory.

11. Do you like to go hunting?

If he hunts for sport, it is a bit alarming. If it is to utilize the animal, you can give him a chance if you are not too iffy about hunting.

12. What is your stance on “chivalry is dead”?

Men seem to be in a state of confusion about chivalry. if you want him to be chivalrous, tell him so after he answers the question.

13. Do you have any usual moves that you do on dates? If so, what are they?

He is probably already pulling out his date moves on you. Let’s see if he will be honest about them with you.

14. People say that a man’s heart is through his stomach, are you that guy?

You can get to know if he is a foodie through and through. You can follow it by asking whether he cooks or not.

15. Have you ever taken any actions to fight off the misogyny of this world?

The world is not kind to women. Men need to make efforts to bring an end to misogyny. Only be with a man who actively fights off the misogynistic society.

16. Are you supportive of your country’s gun laws?

Hunting is one thing but lax gun laws in countries result in death and destruction. Men who want firearms to be common should be kept at an arm’s length.

17. What do you have to say about the concept of “pals before gals”?

There is no harm in this concept on one condition. You should explore whether this concept makes your date support his bros even if they are being unfaithful or disrespectful towards women.

18. How crazy of a fan would you say you are of your sports team?

Some dudes go crazy in supporting their team. You can ask your date if he has any rituals he does to support his team or if he is involved in something crazier.

19. Do you believe in following the social construct of toxic masculinity?

If he says yes to toxic masculinity, run out of there. Run as fast as your legs would carry because that man is dangerous.

20. Have you ever been involved in a physical fight?

The answer will tell you his stance on violence. It is important to always ask his view on physical fights for self-defense, saving someone, or just hurting people.

21. If you were the opposite gender for twenty-four hours, what would you do?

This question will get you all kinds of silly, unusual, and eye-opening answers. It will make the date much more lively and you both would be laughing your hearts out.

22. Do you believe that guys are better than girls at sports?

For his sake, I hope he doesn’t say yes to this one. If he does, he believes in very specific gender roles.

23. Do you think that society has created an unfair power paradigm for women?

The right answer to this is yes. Let’s see if your date is the right man or not.

24. How cool are you with men being involved in “feminine activities” as defined by social convention?

Ask him whether he thinks it is okay for men to put on makeup. Probe and see whether he makes fun of men who wear women’s clothing.

25. I heard guys can down a lot of food in one sitting. Is that true?

Start a conversation about whether he was ever the guy who would eat a lot. One example could be: how many pizza slices can he eat?

Getting to Know You Questions for Her

Fellas, our questions are designed to portray you as an upstanding guy. Women are subjected to discrimination and tyranny all the time. It is up to you to be respectful and keep away from the stereotypes.

1. Are you with or against society’s construct of how a woman should be?

This question will give them space to express themselves. It will allow them to see you in a new light.

2. Do you believe that guys should pay for dinners when dating?

It will tell you whether she considers this as an act of chivalry or an attack on her independence. It will help you act right on the date.

3. What would you want men to do better?

Learn from her answer. See how she sees the world and the changes she wants to see enacted. Be a source of the changes she mentions.

4. Have you ever faced any discrimination because of your gender in any aspect of your life?

The majority will answer yes to this question. It will bring an understanding to you of how women live daily.

5. Who are your women idols that you look up to?

Few men understand how important women idols are. Show her that you respect her gender and her as a person.

6. Do you believe in the regular beauty standards of society?

Many women might not voice it but the beauty standards for them hurt them deeply. Show them that you don’t agree with those standards and mean it.

7. Being a woman, have you ever wished that your country had a female president?

Ask her why don’t we see female presidents in the world? You will be surprised to know how much she cares about it.

8. What attracts you in a relationship?

Truly listen and comprehend what she is looking for in a relationship. Analyze if you are the sort of man who can give her those things.

9. Do you think you fall in love easily?

It could be argued that women tend to fall in love faster. Her answer will tell you how she categorizes her emotions.

10. How much are you willing to spend on makeup?

The majority of women will use some amount of makeup in their life. She might be a big makeup enthusiast which you should instantly note down for future gift ideas.

11. What do you usually carry in your handbag?

The content of a woman’s handbag tells a lot about her. It will give you comprehension of the things she considers crucial.

12. Are you into any physical sports?

Just because she is a woman, don’t peg her down for a non-sports type. Discover whether she is or has ever been into sports or not.

13. What is the one time that you felt proud of being a woman?

As soon as you ask this question, her admiration for you will improve. It will show her that you are truly invested in her.

14. What would you like to achieve in your life?

Most women get asked if they want to have kids, meet the love of their life, etc. I urge you to do better and ask what she wants to do in her life.

15. Do you think that you have to work twice as hard to be recognized and appreciated in this man’s world?

With this, you will give her a platform to be able to speak her heart. You will see through her eyes the things she has been through up till now.

16. Do you prefer home-cooked meals or takeouts?

This is your opportunity to know and note how she likes her meals. You can base your future dates on her answer.

17. Do you go all out in terms of dressing up when going to a party?

The seemingly frivolous question is actually targeted to make her feel confident about herself.

18. Did you ever play with dolls as a child?

It is a stereotype that all girls used to play with dolls as a child. Get to know her childhood by asking the specifics.

19. If you were a man for one day, what would you do?

Only if in imagination, give her the upper hand and see how she responds. It will also let you know what women think men’s privileges are.

20. Would you ever consider going to a finishing school for women?

Finishing schools used to be really popular. They are not everyone’s cup of tea now so get her thoughts on the concept.

21. Do you follow any beauty vlogger or blogger?

When you ask this question, you are going to show that you are interested in them wholly.

22. Did you ever want to be a Disney princess?

Some girls dream about being traditional Disney princesses. Ask them which one is their favorite.

23. What is the one time you felt that you shattered societal conventions?

Empower them and get to know the different ways that they have shocked society uniquely.

24. What do you want men to talk to you about on dates?

This is perhaps the most important question of all. Pray that she is comprehensive about her answer and you will get the key to mastering all dates.

25. Do you enjoy baking or cooking?

Find out if there is any dish she enjoys making. Talk to her about her favorite recipe.

Funny Getting to Know You Questions

When you are getting to know a person (in any situation), it is important to keep the atmosphere light. What better way to do it than by introducing humor?

1. If you could be any vacation, which one would you be?

I personally always say skiing but let’s see what their answer is.

2. Who do you think would win in a fight, a llama or an ostrich?

The mental image of these three animals in a ring is hilarious and is sure to make them giggle.

3. Would you ever do something super embarrassing for a lot of money?

Pick out a few examples for this question. Off the top of my head: braying like a donkey, dancing funny, etc.

4. What is the funniest joke that you know?

The answer they give will be a good addition to your joke diary and it might just make you laugh.

5. Which would you let go forever if you had to: food, money, or your tastebuds?

It is a light-hearted but tough question. Can you imagine losing any one of these things?

6. Which would be worse: never having to do an activity that you love or never seeing the person that you love?

Veiled as a funny question, it will let you get to know the person better. People often pick the person.

7. If you could bring back any animal from extinction, which would it be?

Be a barrel of laughs and ask them their reason for choosing the particular animal.

8. You have unlimited money, which game will you invent?

People have the funniest yet the most creative ideas for this. While encouraging a smile from them, you will get to know how their mind works.

9. Which vegetable do you think is the weirdest?

Most people are not crazy about vegetables, even adults. Hence, making a jibe at them will create a bond.

10. Do you think unborn babies look like tiny goblins?

The correct answer, in my opinion, is yes. One note is to ask it in a funny way that conveys that you are being humorous.

11. What do you think our pets think about all the time?

Every pet owner has this burning question. It is a light topic that will give you an edge.

12. How long can you hold your breath for?

Bring out your stopwatch and challenge them to a friendly holding-your-breath dare.

13. Have you ever tried to fit tiny Oreos in your mouth?

Not everyone is Joey but this query will get them intrigued about the challenge.

14. Do you think that animals can talk to each other in an animal language like they do in the movies?

All of us as children used to wonder about this. I bet that any interesting person would be deeply into this conversation.

15. If given the chance, would you ever live in a house made of your favorite food?

Give them different scenarios like living in a house of cheese, jelly, chocolate, etc. It is an absolute dream topic with anyone.

16. Would you ever smack someone on a bet?

If they yes, you cannot judge them. For a bet, people do all kinds of crazy stuff.

17. What would you do if you ever wake up in the land of Alice in Wonderland?

Start by laying out the scene of where you both are in the world of Alice in Wonderland. Go on an adventure with them.

18. Would you ever like to be the sidekick of any superhero?

With their answer, you can gauge which superhero world they like more. There are so many possible sidekicks that any rational person can go for.

19. If you were invisible for a day, what would you do?

This right here is a golden question. It will tell you the deepest desires of the next person.

20. If I ask you to start a wild conspiracy theory, what would it be?

Conspiracy theories are all wild. Ask them to go as big as they can and see what their beautiful mind conjures up.

21. Do you think that Pluto feels sad to have been kicked out of our solar system?

If your person belongs to Gen Z, they will bemoan about it and you can certainly join in.

22. Is there any weird smell that you enjoy?

Weird smells range from the smell of petrol, magic markers to paint. Coax the answer out of the person to get to know this.

23. Have you ever sent an embarrassing text to the wrong person?

If they have, ask them to show it to describe the scene to you. As long as they are comfortable, you both will appreciate the story.

24. Out of the seven dwarves from Snowhite, which do you think deserves a smack on the head and why?

There are a few that I can think of. Ask them their reason for wanting to wallop a dwarf.

25. What is the worst name you can think of for a baby?

Babies are cute but certain names don’t suit that. Try out a few names yourself and compare them with their choices.

Fun Questions to Ask Over Texts

A conversation through texts can be challenging. You will have to be constantly on top of the game by coming up with riveting topics.

1. If you could be any superhero, which would it be?

Delve into their likes as they tell you the kind of superheroes and powers that they admire.

2. Which is the worst way to die?

It might seem dark but set the pretense that you are asking it in a lively manner.

3. Would you rather date Hulk or Vision?

Both are admirable superheroes from the Marvel Universe. They would be hard to date because of how and who they are, of course.

4. Can you tell me a joke without using the letter “a” in the text?

This is a difficult feat to achieve. If they can do this, hats off to them.

5. What is the funniest meme you have saved in your gallery?

Get to know if they are a meme person or not. The bonus is that you will now have a meme added to your collection.

6. What is your most-used GIF or emoji?

GIFs and emojis tell so much about a person. Ask them to send you more than one if they feel like it.

7. Can you do an impression of any celebrity or cartoon? If yes, send me a voice note of it.

If you feel like you guys are vibing, you can even ask for a video. In exchange, you can send one video/voice note back.

8. What is the funniest text that you have ever gotten?

Since it is a textual conversation, this inquiry fits perfectly. It could be a joke, text from someone they know, etc.

9. When was the last time you ignored someone’s text? Why?

It depends on your skill if you can get them to dish. It can start a very amusing gossip session.

10. What is the most frequently heard song on your playlist?

Music is a way to the heart. Request them to send you that song. It will let you in their world.

11. What is the most interesting photo in your gallery?

I consider this to be exciting because it could be anything. It could be a selfie, a picture from a trip, etc.

12. Have you ever thrown away your phone in anger?

It is a sad tale but maybe they are also one of those people whose phones suffer their frustration.

13. What is your lock screen picture?

The lock screen picture is often of something significant to the person. Implore them to send a screenshot of it.

14. Who has unlimited access to your mobile phone?

The person they name will be someone very close to their heart who has their trust.

15. Would you ever consider proposing to your crush over a text on a bet?

A proposal over texts is never a good idea. If they do it on a bet, they are plenty brave.

16. What kind of funeral would you like when your time comes?

Funerals don’t always have to be a sad affair. Some people wish theirs to be livelier when the time comes.

17. If you could keep any three animals as a pet without trouble, which ones would you choose?

Specify that any and all species would be legal. It could be a giraffe, panda, kiwi, etc.

18. What is one thrilling recreational activity that you wish you could do but are too scared of?

People have their fears but ask them to imagine if they could break free of them.

19. If aliens exist, do they think they are friendly or hostile?

You can follow it up by asking if they think their answer is influenced by movies.

20. Do you think that you could survive a zombie apocalypse?

Do they have an apocalypse plan in place? What tools and strategies do they have in place?

21. If the Purge was real, would you participate in it?

The concept of Purge attracts some people. Do they think it’s deranged?

22. What do you think will happen if everyone starts speaking the truth all the time?

The answer can be found in some Hollywood movies so ask them if the idea entices them.

23. If you could change one thing about the people around you, what would it be?

Would they change their attitude, beliefs, behavior, or how they look? It is not only fun to talk about but will also let you know how they feel about people.

24. Suppose you have a magic wand, what would you change about yourself?

They can reply with a small thing like their nose or maybe it’ll be something deep like how they process their thoughts.

25. What is the weirdest thing that you have done in your life?

Human beings are all some percent weird so where would they rank themselves? Do they have a story behind it?

Best Icebreaker Questions

The point of these questions is to make you guys feel relaxed under all circumstances. The questions are informal so make sure you use them in the right settings.

1. If you could have three wishes, what would they be?

Find out if their reply aligns with the common answers of being rich, pretty, powerful, or living forever.

2. What is on your bucket list?

Better yet, ask them to pull out the list and share it in detail with you.

3. If you could change anything in your life, what would it be?

Give them time to answer because it can be a tough question for some people but it will create a connection between the two of you.

4. What is the best prank that you have ever played on someone?

Pranksters love broadcasting their hit pranks. Get them to open up and boast about themselves.

5.If you had all the time in the world, what would you do?

This will let you know about their interests, dreams, and how they see themselves.

6. What is something that you have done that you are most proud of?

Who doesn’t love to talk about their accomplishments? Find out what they are proud of.

7. Did you ever ditch a class?

When you ask a personal question such as this, it would project that you want to listen to them.

8. Do you have a hidden talent?

You would thoroughly relish the time if they agree to show you their secret talent which could be a skill or an innate trick.

9. What is your favorite time of the year?

What seasons do they like and why? They can tell you about some of the activities that they like doing.

10. In your opinion, what is the best job in the world?

Add o that the job can be a real one or imaginary like the Oompa Loompas working in the chocolate factory.

11. If you could get rid of any global event, which would it be?

There is no shortage of horrible global events like wars, famine, pandemics, natural disasters, etc.

12. If you were the only person on earth, what would you do?

Dig deep and see if they would thrive as the last person or would be lonely.

13. What are the three things that you love about yourself?

The person is likely to get a little shy but you can encourage them. It will be a good boost of self-confidence for them.

14. What are the three things that you dislike about yourself?

They will likely point out their flaws but remind them they should be kinder to themselves.

15. If you did not have to earn money to be alive, what would you do all day?

Would they like to laze around, be social, or do something completely different?

16. How competitive are you in games?

Are they a Monica when they play games or like Chandler? You can even invite them to play the game that you both like.

17. What is the one sound that runs tremors through your body?

For me, it is when someone scratches their nails against a hard surface. Maybe they can come up with something brand new.

18. Do you ever wish that you could have seen dinosaurs alive?

If Jurassic Park has taught us something, dinos are beautiful but they should not be alive today.

19. Is there any weird food combination that you enjoy?

Humans are weird at times and some enjoy weird combinations of food like ranch dressing and cookies.

20. Which is that one TV show that you could not stop binging?

There are so many new shows to binge and drool over so get some ideas from them.

21. Do you remember any vivid dream of yours?

If you meet a lucid dreamer, you are in luck. They will be able to tell you some out-of-this-world stories.

22. Who do you trust the most in your life?

Since it is an ice breaker, be casual about it which means that they don’t need to give you any details.

23. Do you believe in soul mates?

It might seem like a deep question and it can be but it would be smart to scratch the surface only.

24. What is your guilty pleasure?

Some people have a guilty pleasure activity like shopping. It could be gorging on food.

25. What is your favorite game to play?

Dive deep into the types of board, video, sports, etc. Tell them not to hold back and name all.

There are a plethora of other questions to ask to get to know someone better. Feel free to list down some of the questions that worked for you. The first few meetings with anyone are delicate but you can ace them by being polite and charming.

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