100 Questions to Ask Your Friends to Know Them Better

100 Questions to Ask Your Friends to Know Them Better
Questions to Ask Your Friends - Photo by Alexandr Podvalny from Pexels

Tripboba.com - You probably have that thought in mind that you know everything about your BFFs. Yes, you know a lot, but guess what, you can always go deeper to find out more about your close friends.

However, there’s no denying that it can be hard to come up with the right and fun questions, as you don’t want to offend your good friends with personal questions that they don’t necessarily want to hear.

And to help you with questions to ask your friends, today Tripboba has gladly collected 100 questions to ask your friends compiled from many sources for your conversation starters. Check this page out and feel free to pick the ones you get inspiration from!

Questions to Ask Your Friends

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A friend is someone you share your happiness with. To accomplish and succeed this game, you need to know what are the good questions to ask your friends and in what occasion is the game being played.

Questions to ask your friends is definitely a fun game to play to spend quality time with them. Not only it’s good for your health, but playing this fun game can also create a good memory that you will look back in the future time.

Let’s just take a look at these great questions to ask your friends:

  • “Who do you look up to the most, and what qualities do you love about that person?”
  • “What’s your biggest fear?”
  • “How do you like to be comforted when you’re sad or upset?”
  • “What’s your all-time favorite memory?”
  • “When have you felt the most proud?”
  • “When have you felt the most challenged?”
  • “Do you have any regrets? If so, what are they?”
  • “Do you feel like you maybe post to social media too much, or no?”
  • “What’s your favorite thing you own and why?”
  • “When was the moment in your life you laughed the hardest?”
  • “What embarrasses you the most and/or what’s been your most embarrassing moment?”
  • “Where do you want to travel the most?”
  • “Who was the last person who made you cry and why?”
  • “What’s one thing most people don’t know about you?”
  • “If you could only eat one thing for the rest of your life, what would it be?”
  • “What book has impacted you the most?”
  • “If you were going to get some ink, what would you choose and why?”
  • “Which celeb would you want as your other BFF and why?”
  • “If you had three wishes, what would you wish for?”
  • “Do you want to have kids one day? How many?”

Questions to Ask Your Best Friend

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You are in different situations, what would you ask your friend in each situation if you have to? Yep! Random questions to ask your friends in various situations. You can get inspired by these icebreaker questions that Tripboba has found below:

  • “What's the best present you ever received? Who gave it to you and why was it so special?”
  • “If you had to choose only one, would pick a dog or a cat?”
  • “If you were President, what's the first thing you would work to change in this country?”
  • “What's the worst you've ever been physically hurt?”
  • “What's your earliest childhood memory?”
  • “What's your go-to dish when you have to make dinner?”
  • “If you had to live in another time period, what would you choose?”
  • “What foreign language(s) would you want to master and why?”
  • “What's your all-time favorite dessert?”
  • “You just won $10,000 — what are you going to do with the money?”
  • “What's the luckiest thing that's ever happened to you?”
  • “What's your favorite way to exercise?”
  • “If you could only listen to one singer or band for the rest of your life, who would you choose?”
  • “Who was your very first crush?”
  • “If you had to describe yourself in only three words, what would you choose? What words do you think your friends would choose to describe you?”
  • “What's your most embarrassing moment?”
  • “If you could change one thing about yourself, what would it be?”
  • “Do you believe in soulmates?”
  • “What is your most hated chore and why?”
  • “What's your favorite holiday and why?”

Juicy Questions to Ask Your Friends

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Now you’re getting out of a lot of people’s reality, you’re now into your friends’ zone and you can go deeper into them. By asking these questions, you can have a great conversation with them, and what is better than having a great conversation with someone you love?

Here is Tripboba’s version of thoughtful questions to ask your friends with juicy and interesting questions:

  • “Whom do you look up to the most — and what qualities in that person do you want to see in yourself?”
  • “What do you see in yourself that you dislike when you see it in other people?”
  • “What challenges do you most want to overcome?”
  • “When you can't sleep, what keeps you up at night?”
  • “If you won the lottery, what would you do with the earnings?”
  • “What are your top three biggest pet peeves?”
  • “What would your dream vacay consist of?”
  • “What do you see in yourself that you admire when you see it in other people?”
  • “What's your absolute dream job?”
  • “What has your hardest goodbye in life been so far?”
  • “If you had to create an alter ego for yourself, who would it be and what would you name them?”
  • “If you could have a superpower, what would you choose?”
  • “Do you ever wish you’d handled a situation differently? How do you wish you’d handled it?”
  • “What TV show do you turn on when you just want to zone out and feel better?”
  • “When you’re sad or upset about something, how do you like to be comforted? Or would you rather be left alone to process it?”
  • “What is one thing you'd like to cross off your bucket list?”
  • “What's the last lie you told?”
  • “What's the best compliment you've ever received?”
  • “What do you consider the ultimate comfort food?”
  • “What do you consider your best physical feature?”

Weird Questions to Ask Your Friends

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If you ask some of these questions to your friends, what would be their reactions? Cringe? Shocked? Cock their head? Or will you see their wrinkle forehead?

You can find out through these questions to ask your friends. Take a look!

  • “What would you do if you found a dead body in a hotel room?”
  • “If bald people work in a restaurant, do they still need to wear a hairnet?”
  • “Which one would you prefer: have no nose but have really good smelling fingers or be blind but have a really nice smile?”
  • “If you have described something as indescribable, haven’t you already described it?”
  • “Why is it called “beauty sleep” even though you wake up looking like a hot mess?”
  • “What has been the most embarrassing thing you’ve ever worn?”
  • “Which one would you choose: be alive and alone or about to die with a group of friends?”
  • “How many pennies do you think would fit into this room?”
  • “Should a man about to be executed in the electric chair be saved if he had a heart attack?”
  • “Do you think if anything is possible, it’s still possible for anything to be impossible?”
  • “Is it possible to hear someone’s iPod while they’re running at maximum speed?”
  • “Have you ever attempted to swallow toothpaste?”
  • “What music would you choose to play every time you walk into a room?”
  • “Do fish have a thirst for water?”
  • “Is there a limit to how intelligent a single person can be?”
  • “Why is sandwich meat round when bread is square?”
  • “Who’s the fifth person on your missed calls?”
  • “If man developed from monkeys, why do we still have monkeys?”
  • “Which would be the nicest if animals could only talk?”
  • “If you punch yourself in the face and it hurts, are you weak or strong?”

Funny Questions to Ask Your Best Friend

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What is a friend gathering without fun and funny stuff to talk about? This is actually the reason for your friends’ existence, to make you laugh and create good memories together. For more on questions to ask your friends, you can read the funny ones down below:

  • “Is cereal soup? Why or why not?”
  • “What is the sexiest and least sexy name?”
  • “What secret conspiracy would you like to start?”
  • “What’s invisible but you wish people could see?”
  • “What’s the weirdest smell you have ever smelled?”
  • “What part of a kid’s movie completely scarred you?”
  • “What kind of secret society would you like to start?”
  • “If animals could talk, which would be the rudest?”
  • “Toilet paper, over or under?”
  • “Is a hotdog a sandwich? Why or why not?”
  • “What’s the best Wi-Fi name you’ve seen?”
  • “What’s the most ridiculous fact you know?”
  • “What is something that everyone looks stupid doing?”
  • “What is the funniest joke you know by heart?”
  • “In 40 years, what will people be nostalgic for?”
  • “What are the unwritten rules of where you work?”
  • “How do you feel about putting pineapple on pizza?”
  • “What’s the best type of cheese?”
  • “Where is the strangest place you’ve urinated or defecated?”
  • “What’s the best inside joke you’ve been a part of?”


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