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Friendly and Funny Questions to Help You Know Someone in a Happy Way


These funny questions can help you get to know someone better if you are looking to learn more about them.

For introverts and those with social anxiety, meeting new people can be stressful. It is important to find the right questions to ask to get to know people. You’ll be able to quickly recall your favorite lines and not feel awkward.

While you don’t want too many questions or to appear overbearing, it is important to be interested in the conversation. These funny, deep questions will help you establish a connection that is genuine and casual without going too far.

What is in a question?

There are many different types of questions you can ask to help someone. To determine if there is a potential match, the first type of question asks about personal preferences and inclinations.

The second type is one that attempts to determine if the person being asked is bright enough to recognize when certain things should be said or not. No one wants to be a social pariah.

The third type is one that, while suggesting a specific choice of answers to the question, actually seeks out the person’s approach and how they handle the question. We have some funny questions that will give you both a lot of laughs and deeper conversations. It also gives you the chance to assess each other as compatible friends.

How to ask humorous questions to get to understand someone

Keep it light. You don’t want to get too intimate when you first meet someone.

You don’t have to simply ask a question. Share a humorous story that is related so there is a natural flow to the next questions.

Smile and relax. You could look sloppy if you’re nervous or jittery. It’s important not to give off the wrong impression by asking someone serious or funny questions.

It’s about being authentic and open to their answers. Instead of having a Q&A, you need to allow the conversation to flow. Be prepared to answer the same questions.

You will need to get to understand someone if you want to get along with them. These funny questions are a great way to get to know someone. The conversation without your input will feel more like an interview, or worse, an interrogation.

If you want things to be casual, avoid anything controversial

You don’t have to be funny. There’s a place for family-friendly comedy. Avoid asking questions about religion or politics unless you are able to get to know the person. It’s important to be light-hearted when asking questions to get to know you.

Do not ask questions about race, socio-economic status, or any other aspect of your life. Please keep things PG. This is not a place to offend or make these fun get-to-know-you questions into an argument.

A distasteful joke is not only a red flag when you first meet someone, but it can also be a sign that they are a serious or even an immediate offender. First impressions do matter. Keep it simple.

There’s enough drama and fighting in the world. Keep it light and fun. It’s not possible to know the person you are talking about, so it is best to stick with neutral topics.

These are the best and most light-hearted get-to-know-you questions anyone can ask

These questions can be embarrassing or informative, and they even provide a starting point for deeper conversations.

You can choose what you want. You’ll find that you have more confidence and your friends will be more open to you.

It is important to make it easy for people to talk to you and not to make them feel intimidated. These questions will help you get started.

1. Which is your most embarrassing memory?

This is the go-to answer and a timeless classic. There will never be the same answer. Make sure you have your “go-to” story.

This will let you know how serious they take themselves and if it is possible to laugh at embarrassing moments. You can learn a lot about them by asking them to share their stories.

2. Are you gifted with unusual talents?

This is always a fascinating question. You can skip this one if they ask you the same question.

3. Which was your childhood favorite TV show?

It’s always a great way to have a good time and share your memories. It’s a great way to reminisce about your childhood and talk about how you feel today.

Nothing can bring you closer than looking back at your past. Keep the conversation on TV or in movies, as childhood conversations can quickly get heated.

4. Which was your childhood Halloween costume?

A photo of you on your phone is a plus. This question is loved by everyone.

Some people don’t like ghosts or witches. It is interesting to see what they love and how they dress up.

5. Which was your biggest fashion faux pas?

You can have fun with each other and yourself again. It’s always fun to talk about your mohawk, frosted tips, and feathered hair.

It also gives you the perfect transition for a compliment… “Well, you sure did glow up nicely.”

You can bond over the most embarrassing and cringey parts of your past to help you both relax.

6. Which pick-up line is most disgusting?

We can all admit it, it is quite funny to hear such ridiculously bad or corny pick-up lines.

It’s impossible to not laugh when you know that it worked.

7. Which products were you able to purchase from an infomercial?

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Some of the most bizarre products are featured in infomercials. Some are for people who cannot make eggs. Others are for people who don’t have blankets or robes. And some are completely useless.

It is important to find out how this person was tricked into buying the product. This funny question can help you find out if the product is a failure, as they often are.

8. Which two animals would you choose to merge?

Although it can seem strange to ask this question, if you and your partner are animal lovers, it will be fascinating to hear their answers and the explanations behind them.

9. Which dad joke is your favorite?

This topic is funny, lighthearted, and even humorous. Everyone loves a good dad joke. How could we not love a good dad joke? This is one of our favorite get-to-know-you questions. It’s light-hearted and sure to bring some laughter to the forefront.

10. What animal would you consider the most fun if it could speak?

This is fantastic. We all want our pets or cats to be an able to talk back to us. But it would be great to hear what an ostrich, whale, or giraffe thinks.

11. What’s your guilty pleasure?

This is a great way for you to get to know someone else. It doesn’t matter if they are all business-oriented or highly professional. But, it would be surprising and quite hilarious to find out that they enjoy watching The Bachelor or The Real Housewives.

You can also bond with someone who shares a guilty pleasure.

12. Which superpower is the most ineffective?

Everybody asks the question, “What superpower would you like to have?” This is a great question. But, to make it more fun, you can ask this.

Some sidekicks and superheroes just don’t make sense. It can be a creative and fun conversation to talk about hypothetical situations in which these powers might come into play. This is a great way to get to know someone.

13. What would you do if you were to be the opposite gender for one day?

This tells you a lot about a person. If a guy says he stares at himself naked, it could be an indication that he is either too superficial or too horny. This one is funny but can be quite eye-opening.

14. Which song do you have on your phone and would it make you embarrassed if it began playing randomly?

This is one of those hilarious get-to-know-you questions that give you insight into the person’s music tastes and music preferences.

15. Which is your least favorite word of all time?

Although moist is a very popular term, it is still quite funny. Keep the conversation away from food. It is possible to sound quite nasty when you use a lot of your least favorite words.

16. Which is the funniest/worst thing that you’ve ever seen?

People-watching is one of the most interesting and enjoyable activities you can do. It doesn’t matter if you were sitting on a bench at lunch or soaking up the sun at the beach; you have probably seen some of the most hilarious human behavior.

Have you ever seen someone get pooped on a bird? Did someone drop their food outside and still eat it, or did they? Perhaps you witnessed a fight between two people at Taco Bell.

17. Which word are you unable to spell?

This might not be something you think about often, but there are always a few words we cannot spell correctly. Which one is yours? What is yours?

18. What would your boss describe you as?

It can be humorous, embarrassing, or boastful. This can tell you a lot more about the person.

They may feel a bit disillusioned if they believe their boss will have only wonderful things to share with them. Everyone has something that they did at work to make their time passable. If they share it, they can be quite genuine.

19. Do you remember a strange interaction with a celebrity?

Nearly everyone has had the pleasure of meeting at least one celebrity. They are almost always different, whether they were at a book signing or on a plane.

It doesn’t matter if the celebrity is rude or you fangirl hard. This is always a great story.

20. Do you prefer to be completely bald or really hairy?

Here’s a question: Which would you prefer? If your date is actually very hairy or bald, you might skip the funny get-to-know my question. It is quite funny to hear what someone else says.

21. What was your most stupid thing?

Did you attempt a bicycle trick that caused a broken leg? Did you try to egg your principal?

It has to be an epic tale.

22. Which are you most afraid of? Are you more afraid of snakes or bugs?

This one is our favorite because it shows how people react to discussing these sometimes unloved critters.

23. Which is your worst film?

Ask them about the most absurd move or the worst movie.

Did it make you laugh or was it meant to be a parody?

24. Which is the worst food you have ever eaten?

Did you think it would be delicious? It might have sounded awful, but it turned out to be okay. It is easy to talk about food with strangers because it is universally loved.

25. Do you prefer to go on your dream vacation for two days, or do you prefer to have a week at home?

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This will tell you if someone is more a traveler than a homebody. This is what do you share in common? Can you make each other think differently?

26. Which would you prefer, the ocean or space?

Although space is endless, there are still many oceans to explore.

27. What is the dumbest thing that someone could be famous for?

As the meme’s face? Being featured in a local news segment? Is it something you are famous for?

28. What is it that excites you most about being older?

Are you ready to take out your dentures? Do you want to get up early to catch the early bird discount at your local restaurant or go to bed earlier?

It’s not all bad to be old. Which parts are fun?

29. Are you a fan of superheroes?

Imagine if there were villains too. Would you prefer the world to be what it is? If you had to choose one hero who would actually exist, which one would you choose?

30. What’s your most bizarre dating app experience?

This question is full of absurd stories. People are just so strange. It’s very bonding to share your weird experiences.

31. What would you choose if you could only lose one part of your body?

Would you rather pick your pinky or lose an ear?

32. Would you rather visit Willy Wonka’s Chocolate Factory or Jurassic Park instead?

This seems simple enough, but not everyone likes sweets.

33. Which game show would you most like to appear on?

Do you excel at Family Feud! Are you a fan of Family Feud? Maybe The Price is Right is your favorite show?

34. What’s the funniest thing you heard a child say?

Children say the most outrageous things. They do. They even made it a TV series once. What was the funniest thing you have ever heard?

This is a great way to start a deeper conversation with a friend or family member.

35. Which cartoon would you prefer to live in?

The Simpsons? Family Guy? Rick and Morty? Perhaps something more family-friendly like Rugrats?

36. Which law is absurd?

This isn’t law. But it’s an ordinance that says you can’t eat inside your car. What does that mean?

37. Would you rather meet an alien or a ghost?

This is a great question. Which religion do they believe in? Do they prefer the spooky or want to meet E.T.?

38. What are you most unhappy about driving?

What about other drivers? Traffic? Traffic? You must be away from your phone

39. Which name do you think is the sexiest?

George? Miranda? Helen? It’s amazing to see what people are drawn to.

40. Which is your favorite scent?

It’s not about your favorite color or food, but the smell. This is a lot more interesting and telling.

41. Which holiday is the silliest?

Is Valentine’s Day here? Is it International Pancake Day All is well as long as they don’t mention your birthday?

42. Which of these things scared you most as a child?

Did it appear in a film? It could have been in your closet. Perhaps you were afraid of slides or swings.

43. Do you ever pee in the bathtub?

Although it sounds terrible, this is a very common question. You probably already know the answer. This will let you know if they are willing to share it with you.

44. Do you have any accents?

While this can be offensive, it can also be funny if done correctly. You can also use an accent that is totally unrecognizable.

45. Which is your most funny question?

They must be turned around.

46. What makes your blood boil?

You can learn a lot by understanding what makes someone’s blood boil.

This is one of the most important questions you can ask to get to know someone. It can tell you what to do with them to avoid their anger.

47. Who are your heroes in life?

This is a fascinating question because it reveals what their heroes are. They might name Nelson Mandela, Obama, or Mother Teresa as their heroes.

They might say something funny, like Mickey Mouse. You can learn a lot about someone by not asking such serious questions.

48. What would you change about yourself if you could?

It is important to understand how people view themselves. This can help you gain insight into their confidence levels.

You might hear them talk about their appearance or weight. Or maybe they will tell you something about themselves. This is a fascinating question to ask and will help you get to know the person behind their mask.

49. Where would you go if you could live anywhere on the planet?

This question is the best to ask to get to understand someone. It tells you where they are going and what their dreams are.

They could choose an island with coconuts, white sand, and a wooden hut set in the middle of a snowy retreat. They might choose a lively city. This allows you to get to know your person better.

50. Which are the things you are most proud of in life?

This tells you more about the person and their deeper feelings. Knowing what someone is proud of can help you understand what makes them tick.

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This reveals their passions and desires. It also reveals what they are looking for in life. This is one of the most important questions you can ask to quickly get to know someone.

51. What do you do with your spare time?

This could be a great place to start a relationship with someone you are interested in romantically.

52. What has been the worst gift you have ever received?

To get to know someone, you can also ask the opposite question.

They might also say that their auntie gave them a scarf hand-knitted by her and they didn’t like it. This would be a negative statement about them even though it was an awful scarf.

53. What is the best word to describe you?

This is a great way to find out what their perceptions are. You could hear them say things like ‘fun’ or ‘quirky’.

It is fascinating to see the different perspectives of others. It’s possible to see if you share their view or if you need to get to know them better.

54. What would you change about your life if it were possible?

This is a great question to ask to get to know someone in the present. This requires honesty from the person asking it.

It will reveal more than if you just dance around these deep questions. This will also reveal a lot about their life goals.

55. What would you do if you won the lottery?

They must be open and honest. What would they do? Would they give some, spend all of them, invest it or buy a home? What would they do with the money?

This will tell you a lot about them and their priorities. This is one of the most important questions you can ask to get to know someone well.

56. What are your favorite drinks?

You can learn a lot about your character by what you drink, whether it’s a working-class beer or a red-wine-drinking sophisticate.

57. Who would haunt you if you were a ghost?

This is not a chance to see who they will haunt but to gauge their character. You can draw your own conclusions, be they cutesie, creative, or vindictive.

58. Which type of cuisine do your like best?

This can reveal so much. They are sophisticated and intelligent *think French or Vietnamese* or simple and straightforward *American* or German*.

59. Are you a parent?

Someone who claims they love their children but do not want them right now is honest and refreshing.

Worrisome is someone who claims they are unable to bear the thought of having children. Both of these are warning signs.

60. What was the last time that you spoke to your parents?

You have no chance of having a relationship with someone if they are incapable of making that basic relationship work. The answer to “every day for the past twenty years” can lead to relationship problems.

61. Which actor would you choose to portray you in a movie about your life?

This question can help you distinguish between an egotist and a self-hater or comedian from a serious ponderer. This question can reveal a lot about someone’s self-perception.

62. Are you using social media?

It’s not just a question of “yes or no”, but a chance to see how they are doing. Is it gregarious? This question will instantly inform you.

63. What three people would you invite to dinner, dead or alive?

The imaginary invitees will reveal who the person is, whether they are a listener or fighter, a hero or a lover. There is no one right answer. It all depends on what you are looking for.

64. What kinds of books do you like to read?

This is the wrong answer. However, it is useful to find out the cultural preferences of the person being asked.

65. What was the last time you cried.

Refusing to cry is a sign of emotional maturity, which is not desirable.

66. Which has been your greatest success?

This question gives you another chance to identify the rogue materialist. It might also be what some people are searching for.

67. Which is your favorite sport?

Sport can reveal a lot about the people you ask or how social they are. For example, there is a huge difference between a long-distance runner and a football player.

68. What three items would you bring with you to a desert island if you were left without a home?

You might find some very strange things by asking this question. Keep your incredulity private and keep your ears wide open.

69. What time would you go back in history?

Be prepared for weird answers, as is the case with many of these questions.

70. Which type of vacations are you most drawn to?

This is a classic catch-and-match type of question. Vacations are an integral part of a healthy relationship. You need to be sure that those times are moments you can enjoy together in harmony and not just ruminating about what you missed!

71. Which question would you like to ask me the most?

You want to see if they have any questions in mind. If they don’t, it means they aren’t really interested in the topic.

These fun get-to-know-you questions are great for your next date, meeting potential in-laws, or just with anyone. Let’s have a good time and enjoy the moment.

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