100 Questions to Ask Friends

They say, “tell me who your friends are and I’ll tell you who you are” and they are not exactly lying. 

So, if I were you, I would be extra cautious in choosing who I hang around with.

But how can we truly know our friends on a deeper level?

There’s only one way to find out: you have to ask them. 

Conflicted about where to begin? Here is our list of 100 brutally honest questions to ask to every type of friend you have for that much need heart-to-heart conversation:


The Overachiever 

We all have that friend who excels in just about everything. If you are friends with someone who seems to achieve all these things you never could in this lifetime, these questions are the surefire ways to know more about her and the passion that drives her.

  1. What’s in it for you?
  2. What is that one strong thing that keeps you going?
  3. How good or bad do you handle disappointments?
  4. Do you secretly look down on me?
  5. Do you want to overachieve because that’s what you want to do or because that’s what you are expected to do?
  6. Have you sacrificed a lot of good things for the sake of achievements?
  7. What is something you regret until now?
  8. To whom do you owe your success?
  9. What’s something that sets you back?
  10. Are you willing to betray me in exchange for an academic/work recognition?


The Scene Stealer 

Spotlight, sass, and style just thinking about these three things makes a certain friend pop in your head. That person is the life of the party and the darling of the crowd, sometimes a little way to overboard. For that attention-grabbing friend you’ve always had around, it’s best to ask him/her about these juicy questions about her life.

  1. Honestly speaking, do you think everyone around you is drawn to you?
  2. What is your zodiac sign?
  3. What is your secret to feeling good about yourself all the time?
  4. Do you really think you are the life of the party?
  5. Have you ever been intimidated by someone?
  6. Have you ever been turned down by someone you approached?
  7. As a scene-stealer yourself, what would catch your attention?
  8. What’s the next daring look you would like to try?
  9. What do you think of my fashion style?
  10. Who among our mutual friends do you think is your opposite – the most boring one?

Next: 100 Get to Know You Questions


The Co-workers 

If you’re already an adult, then, chances are, you spend most of your time around your workplace. You see the same faces over and over again and talk to the same people EVERY SINGLE WORKING DAY OF YOUR LIFE! 

Most conversations you have with these people are strictly about your work, you might even realize while reading this that you don’t know the story of that workmate that you talk to every day. For an ice breaker, here are some questions that you can ask to know more about them:

  1. How did you land this job?
  2. Are you new to this industry?
  3. What was your first impression of me when you first saw me at work?
  4. What’s my most annoying habit while working?
  5. What do our workmates think of me?
  6. Who is your work crush?
  7. Have you ever had intercourse with one of our workmates?
  8. If we’re not working together, do you think we would still be friends?
  9. Do you like our current job?
  10. Do you think we are being underpaid?


The Travel Enthusiast 

If you browse your social media, there is always one friend who seems to be out on an adventure. Whether it is travelling out of town, or out of the country, they just always have something going in their life. While you, on the other hand, have been living the last ten or more years in your life in the same place, and do the same things. 

If you’re curious to know how it feels, but feels so shy to ask your friend about it, here are some questions that will surely help you build a conversation with them:

  1. When did you find your love of travelling?
  2. How many countries have you visited?
  3. What’s your favourite country to visit?
  4. What’s your least favourite country to visit?
  5. What’s the wildest thing you’ve ever done while you’re out of the country?
  6. Where is your dream destination? 
  7. If you could live in one country aside from your own, where would you want to stay?
  8. Do you ever wish that we could go on a trip together?
  9. Were you ever treated differently just because you are a tourist?
  10. What’s the best and worst part of travelling?

Next: 100 of the Best Yes or No Questions to Ask Your Friends ASAP


The Mature One

Smart, well-put-together, and seems to know what’s their purpose in life, we could all agree that there are SO MANY things that we wanna know about a mature friend. But, it sometimes feels awkward to talk to them because we might feel a little intimidated.

Don’t worry, we got a list that will help you start a chat with them!

  1. What’s the most annoying stereotype about being a grown-up?
  2. What do you think is the most stupid thing that you have done when you were young?
  3. What is your motto in life?
  4. If you could change something you did in your past, what would you have done differently?
  5. What is the most childish habit of yours?
  6. Do you think you have everything figured out?
  7. What are the things that you still want to achieve?
  8. What is your greatest lesson in life?
  9. Who is your role model?
  10. What’s your biggest insecurity?


The Half-Friend Half-Foe 

Ever had a friend who acts like an enemy when you’re not around? We all have one, and that’s exactly what gives life a little dash of drama. If you’ve always been looking for the perfect timing to confront them, these following questions are the most spicy ones to ask as a much needed slap-in-the-face.

  1. Why do you have to be so two-faced?
  2. Do you consider me more as your friend or as your enemy?
  3. Despite our fights, why do we stay friends?
  4. What is it about me that you are most envious about?
  5. If the situation is different, would you rather me as a friend or as an enemy?
  6. What was the reason behind our biggest fight?
  7. How many false stories have you spread about me behind my back?
  8. How many rumours about me have you believed in?
  9. As Regina George asked, why are you so obsessed with me?
  10. Do you think we’ll ever be good friends without the backstabbings?

Next: 200 Fun Things to Do With Your Friends


The Bunkmate 

Living in the same household for quite a while now, it seems like your roommate would be the friend you know the best. But do you, really? Throw in these set of questions into your daily conversations and watch yourself get surprised in more ways than one with what you will discover afterwards.

  1. How was living with me like?
  2. What do you think is the best part of us being roomies?
  3. Have you ever done something nasty without me in the house/condominium/apartment?
  4. What do you hate most about living together?
  5. Did you ever break or use some of my stuff without telling me?
  6. If you could pick another roommate better than me, who would it be?
  7. Have you ever secretly caught me doing something dirty?
  8. How many guys/girls have you sneaked in without me knowing?
  9. What’s a dirty secret of mine you have discovered that you never had the courage to ask me about?
  10. Did you ever think that you are better off living alone?


The Academically-Inclined

Ever felt curious about what it feels like to be smarter than everyone else? Well, this list might not help you be a genius in a snap of a finger, but it will surely help you talk with one.

Check out the list of questions below, for you to know what a smart person feel like:

  1. Do you enjoy what you do?
  2. Aside from studying, what else do you like doing?
  3. Do you also find me intellectual?
  4. What’s one thing that you learned or realized because of me?
  5. Do you think you are smart?
  6. What do you feel when people call you bright?
  7. Do you ever wish that you are not as smart as you are right now?
  8. Do you ever feel judged because of your wit?
  9. What do you think are the advantages/disadvantages of being witty?
  10. Is there a part of you that feels more superior to others because of your brain?



More than friends but less than lovers. With your unusual, highly-adventurous friendship, you and your FUBU spend most time on the action rather than the talk. You’ll be lying if you tell us you never wanted to know what goes on his/her mind. Dab in some of these questions below who knows – maybe you can have some pillow talk with these conversation makers.

  1. What’s the best part of this kind of “friendship”?
  2. Why did you settle for this?
  3. Were you ever taken when we had this friendship?
  4. Do you have other f*ck buddies aside from me?
  5. What is it about me that turns you on?
  6. What’s the nastiest experience you had with me?
  7. Have you ever thought of me as someone more than a “no strings attached”?
  8. Have you ever caught feelings for me?
  9. When are you planning to put an end to this “friendship?”
  10. Do you have any plans to take this to the next level?

Next: 100+ Funny Dares for a Wild Time with Friends


The Ultimate BFF

Whether you call it your soul mate, your best bud, or your friend for life, it really feels nice to have a friend that will stick with you no matter what.

Being able to share your lives with each other for years, it will seem like you have nothing more to learn about each other.

WRONG! No matter how long your friendship might’ve been, there are still a lot of things to learn about your partner.

To know more about them, here is a list of questions that will surely help you discover new things about your best friend:

  1. Why do you think are we best friends?
  2. If you would be given 10 Million to punch me in the face, would you do it?
  3. What was the moment that made you realize that I am your best friend?
  4. What’s my most annoying habit?
  5. What’s one thing that you’ve always wanted to say to me but you couldn’t
  6. Are you proud of me as your best friend?
  7. What’s one thing that I’ll do that will make you give up on me?
  8. How do you describe me to your other friends?
  9. Do I do things that offend you?
  10. Am I a part of your future plans?
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