40 Deep Questions to Ask Your Friends About Yourself

You may believe that your pals know everything about you. However, ask your friends these deep questions from our post and be amused at the answers you’d get. The main aim of these questions is for you and your friends to get to know each other better and to have a good laugh when you share your opinions and experiences – so do not get offended by what you hear; just play the game with high spirits!

Deep Questions To Ask Your Friends About Yourself

Sharing personal information is one feature of true friendships, and it is on this basis that a strong bond between friends is forged. You might begin by asking simple inquiries before progressing to more complex issues. The list we have compiled below will supply you with numerous questions to ask your friends that will give you an insight into how well your friends know you:

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1. What is the most daring thing I’ve ever attempted?

Do your friends think you’re a daring or an adventurous person? Maybe you’ve been telling stories of your adventures, and now it’s time to know if they’ve been listening or zoning you out.

2. Which season is my favorite?

What season gets you up and going- Summer, Spring, Autumn, or Winter? Ask this question to know if your friends can tell you at what time of the year you usually enjoy yourself the most.

3. Which gift has been the most memorable for me?

Gifts can be a touchy subject. It’s one thing to give someone, and it’s another for the receiver to like the gift. What’s your most cherished gift, and do your friends know what it is? Ask this question and find out!

4. What do I like to do when I have nothing to do?

How do you occupy your free time? Your close friends should be able to guess this easily. It’s something that should come up in the most casual of conversations.

5. Do I usually compete with others a lot?

If you’re a competitive person, your friends should be able to know. It might even be with them. However, ask this question to get to know their opinion about you.

6. What is my most memorable life experience?

Some events or experiences stick more than others. If your friends know you as much as they should, this should come easily to them.

7. Which book is my favorite?

Books, like movies, have such a huge impact on us. Favorite books can shape your life, so your friends should know this!!

8. Do I have a hidden gift that no one else is aware of?

What secret talents do you have? Singing, writing, drawing, ventriloquism?? Maybe your friends have figured it out, or you probably shared it with them in the past. Ask them and find out if they will remember.

9. Have I ever had a friend deceive me?

Sometimes, life is not always rosy. Betrayals and deceit by friends can happen to anyone. If you’re as close to your friends as you think, this is information they should know.

10. What is my greatest fear?

Do you think your friends know your greatest fear, or have you shared it with them before? You can check if they remember by asking them this question.

11. What is my favorite television show or film?

TV shows and movies sometimes inspire a cult-like following, and you probably have one you are crazy about. Maybe a movie you’ve seen a hundred times or a TV show you can recite all the dialogues in it. If you are as close as you think you are with your friends, they should know this. Ask them and see if they know what you usually indulge yourself in.

12. Do I suffer from any allergies?

For your safety, if you have any allergies, our friends should know about them and the protocol to follow during a medical emergency. This could literally save your life when the need arises. So, ask them this question to know if they have any clue at all about your allergies.

13. What is my favorite musical genre?

Being friends means you have hung out with each other a lot and vibe to music together. Your friends are expected to know your tastes in music and favorites. So, find out what they think is your favorite – pop, hip hop, rock and roll, afro beats, or the good old jazz!

14. Which destination would I choose for a vacation?

Where is the one place you’d love to escape to? Many friends share vacations and holiday plans, so this should be easy. However, you can still ask your friends this question to ensure that they know about your dream vacation.

15. What irritates me the most?

Well, we all have pet peeves and triggers. What’s yours and do your friends know? If they don’t know, this could cause a lot of friction in your relationship. Take advantage of this question and answer session to let them know about those things that irritate you the most.

16. What was my nickname as a kid?

If you had a nickname as a child, most of your friends might know about it, especially your childhood friends. You probably hated it, but try asking and see if your friends still remember the name.

17. Do you see me as a miser or a generous person?

Are you tight with money, or are you the one who’s willing to pay everyone’s tab after a night out? Again, remember not to be offended by any response. It is a fun game!

18. Which word best describes me?

If they were to describe you in one word, what would it be? Sassy, cool, funny, quirky? Whatever their reply, do you think it aptly describes you? Get to know their opinion by asking this question.

19. What are the most irritating characteristics I possess?

Everyone goes a little overboard with some things or attitudes at times. Try and know what your friends think about your attitude. However, be open to hearing the truth and not getting offended. Getting angry and sulky will ruin the vibe of the game.

20. What designer item would I love to own?

A Chanel bag? Micheal kors wristwatch? Gucci shoes? Versace dress? What is the one luxurious item you’d love to win or be gifted? You’ve probably fantasized about them with your friends, so ask them and see if they take your wishlist seriously.

21. What is my dream car?

Maybe you dream of a Lamborghini or Ferrari car, do your friends know you love such cars? Find out with this question.

22. What will I do when I retire?

What are your retirement plans for your sunset years? Want to retire to somewhere warm with a beach? Buy a house in the country with a garden? Volunteer your time to social services? Retirement is a big deal and an integral part of our future. See how much your friends know your plans for the future with this question.

23. What’s the most embarrassing thing that has ever happened to me?

You know that moment you remember, and you cringe, and you want to expunge it from your memory? Your friend probably knows the story, and in fact, you might have shared the moment with them. However, you can still ask the question to hear their responses.

24. What’s the craziest thing I’ve ever done?

Your finest unhinged moment is one your friends should know about. What do they think is your craziest experience, and can they ever guess the correct answer? Ask them.

25. Do you consider me optimistic or pessimistic?

Are you a half full or half empty glass kind of person? Do you see the world through rose-tinted glasses? Know what your friends think about this question.

26. What has been the longest relationship I’ve ever had?

Who else should know all your romantic relationship travails and journeys more than your friend? Walk down a memory lane with them and see who will remember the longest relationship in your life.

27. What is my favorite memory from our time together?

This could be a hilarious moment or one that tugs at the heartstrings. More so, it would be great to know whether your friend can guess your favorite memory with them so far.

28. What is the one thing that will always put a smile on my face?

What’s the thing that gets you excited and bubbly with happiness and joy? It could be a fun activity or event, or even an item. Ask this question to see whether your friends can get it right.

29. Would you call me a night owl or early bird?

Who else will know about your sleeping habits better than your friends? You can ask this question to verify who amongst your friends knows you better.

30. If I could change my profession, what would I choose?

Your friends should know what kind of profession you admire, even if it has nothing to do with your expertise. However, you can ask this question to test how well they know you.

Funny Questions You Can Ask Your Best Friend About Yourself

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Even though these questions are designed for you to get to know how well your friends know you, they don’t always have to be stiff. You can choose to ask questions that will make your friends laugh or give hilarious responses.

Below are fun questions you can ask your friends about yourself:

31. Am I a bathroom singer?

Do you turn into Beyonce or Adele while taking a shower? The more time you’ve spent with your friends, the faster they’ll find this out. However, ask this question to know what they think about your bathroom moments.

32. Do I know how to cook?

This question will crack them up if they know you are terrible at cooking. Whatever the case, don’t take it too seriously. Just enjoy your game time with your pals.

33. What celebrity is my current crush?

Most people have that celebrity they are crazy about. It could be a musician, actor, or influencer. Your friends should easily know the answer to this question.

34. Which dessert is my favorite?

Are you a sweet tooth? When you go to dinner, what dessert are you most likely to order? The one, your friend, can order in your absence and be assured that you would love it – know what your friends will say when asked this question.

35. What are my favorite pizza toppings?

Do you go a bit crazy with your food? Pineapple on pizza or do you do pepperoni and sausage like other normal people? Get to know how your friends rank your food choices with this question.

36. What will I buy first if I win the lottery?

Everyone wishes they would win a million dollars at the lottery. I mean, that would be glorious. What would you buy if you won it, and would your friends guess correctly? Find out by asking this question.

37. Which fictional best friend duo is the most similar to our own?

Their response could be similar to a duo from your favorite TV show or movies. However, though this is a fun question, it throws light on what your friend thinks your relationship dynamic is like.

38. Food or sleep – which one would I give up if I had to?

It’s a silly and hilarious question, no doubt, but still! Which would you rather live without? Let your friends decide which of the two they think you will forgo if you had to and see if they are right.

39. Name the pettiest thing I have ever done?

If your friends know you as much as they should, they should be able to name the pettiest thing about you. Ask this question to find out.

40. Will I skip brushing my teeth or my hair when running late?

Ask this question to know whether your friends can tell what you will skip if you are running late. They should know this answer, especially if you are a perpetual latecomer but just have fun asking.


No matter the type of question you would like to ask, it is essential to know that this game aims to have fun with friends. The responses you get will foster and create memorable experiences while enabling friends to learn more about each other. Keep this in mind while playing this game, and have as much fun as you can! You can also check out Deep Questions to Ask Your Best Friend.

Tyna G
Tyna G
Tyna is passionate about sharing authentic news and giving her readers great content. Apart from writing, she is a music enthusiast who enjoys watching good movies


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