Some Controversial & Juicy Questions to Ask Friends

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How many friends do you have?

I suppose many. Now, you don’t know all of them from your childhood, right?

Maybe there are some whom you know from your school life, some from your college life, some from your work, and maybe some you have just met. This means you don’t know everything about them.

You know, like other relationships, friendships, too, need time to nurture, grow and become an unbreakable bond. So the more you spend time with your friends and know them well, the more you get attached to them. And there is no end to knowing more!

Now, if you want to know more about your friends, you need to ask them questions. From random relationships to family and controversial – there are so many types of questions that you can ask your friends.

Don’t get all puzzled thinking about what questions to ask. I have come up with a list of some controversial questions to ask friends to help you. Have a look at these, and I am sure you will get some inspiration.

Happy reading!

Controversial Questions to Ask Friends

Friendships are pure, and friends are to be meant forever. All you need is to communicate with them, and you will have a relationship of a lifetime. And for that, you can ask them these questions!

Questions to Ask Your Friends About Yourself

Questions to Ask Your Friends About Yourself

Our friends are nothing less than our family, isn’t it? And some of them have even become our family. Do you want to know what they think about you?

Ask them these questions about yourself!

  • If I give you four words to describe me, how would you do that?
  • Do you like to spend time with me?
  • Do you like it when I call you and ask you to meet me when you are at work?
  • Do you like it when I accompany you almost everywhere?
  • How do you feel when I borrow your dress? Be honest
  • How do you feel when I say I don’t have time when you ask me to meet you?
  • What, according to you, is the best time you have spent with me?
  • What, according to you, is the worst time you have spent with me?
  • What is your favorite memory of us?
  • Do you remember the first time we meet?
  • Do you remember what we talked about when we first met?
  • What did you think about me before we actually started talking?
  • What, according to you, is the worst trait that I have?
  • Do you think I’m annoying?
  • Do you think I’m boring?
  • Do you want to go shopping with me?
  • Do you think we have the best kind of friendship?
  • Where do you see our friendship in five years?
  • Do you think we will remain friends even after five years?
  • Do you think we will still have time for each other after five years?
  • What kind of clothing brings out my best feature?
  • What is my worst feature, according to you?
  • Do you think we will still have for each other once we start dating other guys?
  • Do you know what my favorite food is?
  • Do you know who my favorite actor is?
  • Do you know what my favorite movie is?
  • Do you know what annoys me the most?
  • Do you know which trait in people makes me cringe?
  • Do you know which is my favorite drink?
  • Do you know what kind of vacation destination I prefer the most?
  • Do you know who was my first ever crush?
  • Do you know how I felt after my breakup?
  • Can you tell me who my favorite person in the whole world is?
  • If someday I go missing, do you know where to find me?
  • Can you tell what my dream partner looks like?
  • What is that one quality in me that you think is sweet?
  • What is the craziest memory you have of our friendship?
  • What is the stupidest memory you have of our friendship?
  • I am your best friend?
  • If I ask you to rate me in terms of friendship, what would you score me between one and ten?
  • Do you trust me?
  • How far would you go for the sake of our friendship?
  • Do you think we are meant to be friends forever?
  • What trait in me do you dislike the most?
  • What is the naughtiest thing we have done together that you can remember?
  • Do you remember when my birthday is?
  • Do you remember the date we first said hello to each other?
  • Do you think we both have similar traits?
  • Have you ever imagined how your life would be without me in it?
  • What kind of job, according to you, will be the best for me?
  • Do you think I am a good person?
  • What kind of person do you think I am?
  • Do you think I will ever do anything to hurt you?
  • Do you know which my favorite restaurant is?
  • Do you know which kind of cuisine I am fond of the most?
  • Will you ever leave me for some other friend?
  • Do you know what my favorite color is?
  • Will you pick up my call if I call you at 3 a.m.?
  • How will you introduce me to your other friends?
Career-Related Questions to Ask Your Friends

Do you want to know what career choices your friends have made and if they have made any mistakes in their choices?

Ask them these questions related to their career!

  • What is the one thing that you like most about your job?
  • Would you like to stick to this company you are working with, or are you open to change?
  • What is the one thing that makes you work hard?
  • What keeps you going in your job?
  • Would you like to change your company every year or want to be in it for a long time?
  • Do you think you will be able to grow your salary if you stick to the same company for years?
  • What, according to you, is the best way to increase your salary?
  • What do you love the most about being independent?
  • Have you always wanted to be independent, or have you just gone with the flow?
  • Where do you see yourself in the next five years?
  • If the company you work in wants to send you to a different country at their client office and work from there, would you accept the offer?
  • If you could stay in your current company only by enhancing your skills and learning new work, would you do it, or would you look for a job in a different company where your current skills are sufficient?
  • What, according to you, is career growth?
  • Do you like your job or your office more?
  • Would you like to relocate for your work?
  • If you get to choose between permanent work from the office with more salary and permanent work from home with a lesser salary, which one would you prefer?
  • How long has it been that you have been working in this company?
  • What, according to you, was your biggest achievement last year?
  • What is the one thing that motivates you every day to work harder?
  • What do you prefer more – work harder or smarter?
  • What do you have to say about those days when you need to stay at the office much longer than your usual working hours?
  • How do you feel when you need to work overnight by staying at the office?
  • Have you ever missed any deadline for work? If so, what was the reason behind it?
  • If you get a better salary package, would you like to change your job at the moment?
  • What is success according to you?
  • Have you ever got an appreciation for your work in your office?
  • How was your first day at work like?
  • What is the one thing that you dislike the most about your job?
  • Is the project that you are working on right now exciting? Or is it boring?
  • Are you doing this job because your parents wanted you to do so, or are you doing it because you wanted to do it?
  • What does your average week at the office look like?
  • What perks do you have with this job?
  • Are you happy with your current salary package?
  • Do you think that your current salary package has done justice to your skills? Or do you think you deserve more?
  • What was the best interview you have ever had?
  • What was the worst interview you have ever been to?
  • When you were a child, and you got asked what you want to become when you grow up, what was your answer to it?
  • Are you living your dreams right now?
  • Are you into the same profession that you have always wanted?
  • Do you think you are the right match for your current job?
  • Do you prefer to follow a to-do list that has been long scheduled? Or do you now want to follow any to-do list and complete tasks when it comes?
  • What are your aspirations regarding your career?
  • In what designation do you want to see yourself in the next ten years?
  • Have you ever dreamed of forming a brand of your own?
  • What do you prefer more: a salaried job or a business?
  • How good are you in finance?
  • Do you manage your own finance, or do you take help from a professional?
  • What do you do when you can’t solve a problem?
  • What dreams do you have regarding your career?
  • What would you prefer more: making a lot of money doing a job that you don’t enjoy or making not much money doing something you love?
  • Have you ever thought that you would end up doing the job that you are currently doing?
  • Do you do freelance?
  • Do you think it is possible to handle two jobs at the same time?
  • Who is the one person that you look up to in your professional circle?
  • Did you have a mentor? If so, what was he like?
  • What is the best career advice you have ever got?
  • What is the worst career advice you have ever got?
  • Who is that one person that you go to in your office whenever you have a problem, and you need a solution?
  • What kinds of colleagues have you always had?
  • Do you think you can make your passion your profession?
  • Did you have to leave for passion for your profession?
  • Is there any career advice that you want to give others?
  • Do you think you got into the job at the perfect time?
  • What are your thoughts about enhancing your skills and landing a better job than you are currently doing?
  • Has it ever happened to you that you rejected the better-paying job offer just because you love working in this current office?
  • Do you regret any decision that you made regarding your job?
  • What is your biggest regret regarding your career?

Deep and Meaningful Questions to Ask Your Friends

Deep and Meaningful Questions to Ask Your Friends

We don’t always want to have fun, right? There are times when we have some serious talk too. So, do you want to have a meaningful conversation with your friends?

Try asking them these controversial yet serious questions!

  • If you were asked to give a title to this chapter of your life, what would you give?
  • What is that one thing that keeps you going even when you don’t feel like it?
  • Whenever you are sad, what do you do or what do you hear to pick yourself up?
  • Can food make you happy?
  • What is that one food that can make you happy no matter how sad you are?
  • If you had only one week to live, how would you like to spend it?
  • What do you generally do – follow your heart or listen to your head?
  • Can you think of the best advice that someone has ever given you?
  • What is the one thing that you are most thankful for in your life?
  • What is that one thing that you still regret doing?
  • What is your take on life?
  • Have you ever lost someone very close to your heart? How was the feeling?
  • What do you fear the most?
  • What is the one thing that makes you feel that you are unstoppable and you can accomplish anything and everything you want?
  • What do you do when you are down?
  • Whom do you look up to?
  • What would you change if God allowed you to go back to your past and change one thing?
  • What are your thoughts on people in general? Do you think they are mostly evil or good?
  • Who is the most selfish person you have ever come across?
  • Have you experienced any life-changing incidents?
  • What do you do when you think you need some motivation?
  • Is there anything that gives you hope?
  • When you leave earth, what do you want people to remember about you?
  • What is there on your bucket list this year?
  • What do you generally do? For example, do you tend to judge a book by its cover?
  • Do you want to have kids in the future?
  • What kind of a parent do you want to be?
  • Have you ever seen poverty in your life?
  • What lessons have life taught you?
  • Are you an extrovert or an introvert?

Juicy Relationship Questions to Ask Your Friends

Juicy Relationship Questions to Ask Your Friends

You know how some questions and answers can stir controversy, right? This is especially true for relationship questions.

So, are you up for some controversial questions to ask friends?

Start with the following!

  • Have you ever been on a blind date?
  • Have you ever fallen for someone who is already taken?
  • Have you ever had a one-night stand?
  • Do you believe in love at first sight?
  • Have you ever fallen for someone just by hearing their voice over the phone or radio?
  • What does the person of your dreams look like?
  • What are your thoughts on blind dates?
  • Have you ever thought of cheating on your partner?
  • Have you ever thought of someone else while making love to your partner?
  • Have you ever lied to your partner about some other guy?
  • Do you think it is good to share everything with your partner, or do you prefer keeping at least some things from them?
  • Do you think you love your partner a lot?
  • Do you trust your partner with all your heart?
  • Did you ever get the thought that your partner might be cheating on you all this while?
  • Do you want to see your partner as your future husband or wife?
  • Do you want to spend the rest of your life with your partner?
  • Do you think you have the best partner, or do you think you could have got someone better if you waited a little bit more? Be honest
  • Do you think your relationship is perfect, or do you think there are scopes of improvement in your relationship?
  • Have you ever thought of ending the relationship with your partner? If so, when?
  • Who would you save if you were drowning and left with the chance to save yourself or your love?
  • Have you ever thought of your partner being with someone else?
  • When your partner talks with other guys or girls, does it makes you jealous?
  • Are you an attention seeker in your relationship?
  • Do you think you can see your partner with someone else if you break up?
  • Have you ever regretted being in a relationship with your partner?
  • Does your partner love you more, or do you love them more?
  • Who is the superior one in your relationship, or are you both equal?
  • Do you believe in giving or receiving?
  • Can you imagine your life without your partner?
  • Have you ever experienced love at first sight?
  • Have you ever slept with a stranger?
  • What are your thoughts about role play? Do you want to try it in your relationship?
  • What is the best lesson your relationship has taught you?
  • What is your relationship advice to singles?
  • Do you wish to start a family sooner or later?
  • What, according to you, is the perfect definition of a perfect date?
  • Have you ever gone on a double date? What is your experience?
  • What attracts you the most: your partner’s intelligence or their beauty?
  • What is the most romantic date that your partner has arranged for you?
  • Do you think you give your partner the respect that they deserve?
  • Do you guys fight a lot?
  • What do you do after a fight? Do you go to sleep angry, or do you both sit together and resolve the problem before going to bed happily?
  • If your partner needs to relocate to a far away location for their career, would you support them and continue your long-distance relationship, or would you break up with them as you think long-distance relationships don’t work?
  • Have you ever played with your partner’s emotions?
  • Have you ever taken your partner for granted?
  • Are you more of a social media person who posts all the details of their personal life, or are you more of a private person who likes to keep their relationship private?
  • Have someone ever broken your heart? How did you deal with it? How much time did it take to get over them?
  • Have you ever done something so romantic for your partner that it literally brought tears to their eyes?
  • Do you think you have got the best partner with whom you see your future?
  • Do you and your partner have love languages?
  • Suppose you got to know that your partner has cheated on you with your best buddy. Would you ever accept them and forget what happened? Or, would you never keep any relationship with them?
  • What is the sweetest trait that your partner has?
  • Have you ever lied to your partner?
  • Have you ever gone on a date with someone else while still being in a steady relationship? Be honest.
  • Have you ever double-timed in a relationship?
  • What is the best memory that you have of your relationship?
  • Did you and your partner click the first time you talked to each other, or did it take quite some time to fall for each other?
  • Who among you and your partner expressed their feelings first?
  • If you are the one who expressed their feelings first, did your partner play hard to get?
  • Are you a good kisser? If I ask you to rate yourself on a scale of one to ten, how much would you rate yourself?
  • Do you think you and your partner are soulmates?
  • Have you ever questioned yourself if you are really in love or if it is just infatuation?
  • What is the most embarrassing incident you can remember when you went on a date?
  • Who, according to you, was the worst partner you ever had?
  • What is your most embarrassing kiss story?
  • Have you gone on a blind date only to find out that the person you came to see is the person you hated the most?
  • What is the most embarrassing thing you have in bed?
  • Have you ever accidentally farted while doing the thing?
  • How far would you go just to make your partner happy?
  • Have you ever received gifts from an unknown person?
  • What is the craziest thing you have done in front of your partner?
  • What do you generally do so that you can attract the attention of your lover?

Controversial Questions to Ask Friends About Family

Controversial Questions to Ask Friends About Family

Do you have friends whom you have just met and don’t know much about their families? Then it is time that you ask them about their family. You can start with the following questions!

  • If you were to choose between your mom and your dad, whom would you choose and why?
  • Are you on good terms with your parents or not?
  • How much time do you spend with your family on a regular basis?
  • Do you share most of the things with your parents?
  • Do your parents know about your girlfriend or your boyfriend?
  • How do your parents reach when you take your partner home?
  • Have you ever taken your partner to your home?
  • Have your introduced your partner to your parents?
  • Do you tell your parents about how your day was?
  • Which of your family members is your closest?
  • Do you have siblings? How many? Which one is your favorite?
  • Do you love spending time with your siblings?
  • Who cooks the best in your family?
  • Have you ever wished to be the only child of your parents?
  • What is your equation with your grandparents? Do you love their company?
  • How were you as a kid?
  • Were you a good kid or a rebellious kid?
  • How were you as a student?
  • Did you use to listen to what your parents said or did you do what you wanted?
  • What is the best childhood memory you have of your siblings?
  • Did you use to fight a lot with your siblings, or were you friends with them?
  • What do you think is the most difficult part about staying away from your family?
  • Do you know how to cook?
  • How close are you to your sisters and brothers?
  • Have you ever brought any gifts for your parents?
  • Have you ever brought any gifts for your siblings?
  • Do you celebrate your parents’ wedding anniversary with your family?
  • Do you remember your parents’ birthdays?
  • Do you remember your parents’ anniversary date?
  • Do you remember your brothers’ and sisters’ birthdays?
  • Have you ever brought gifts for your siblings from your own hard-earned money?
  • How would you do that if I gave your five words to describe your family?
  • Have your parents given you any nicknames? What is it?
  • Have you given your siblings any nicknames?
  • Do you remember your parents reading your bedtime stories before they put you to sleep?
  • Can you remember your favorite story that your grandparents told you?
  • Do you love spending Christmas with your family?
  • Which is your favorite holiday to spend with your entire family?

Weird and Funny Questions to Ask Friends

Weird and Funny Questions to Ask Friends

Are you up for some light-hearted conversation with your friends and having a good laugh?

Ask them these weird questions, and have a great time!

  • Have you ever winked at someone thinking that they are your partner, only to find out that they are not?
  • Have you ever farted in public and then realized that someone had heard it?
  • Have you ever fallen on the stage while performing?
  • Has anyone ever accidentally seen you naked?
  • What was your big failure moment?
  • Have you ever copied your guardian’s signature and got caught?
  • What is the lamest joke you know?
  • Have you ever tried to impress someone but failed in front of everyone?
  • If you could ask for a useless superpower, what would you ask for?
  • What is the stupidest thing you have done on a first date?
  • What is the funniest thing you can remember you did?
  • If you could be an animal, which animal would you choose to be?
  • Can you describe the funniest smell of something you have ever sniffed?

Also Read: No Such Thing as a Perfect Friend


So, here is my list of controversial questions to ask friends. Do you want to add some more to this list?

Don’t forget to let me know in the comments!

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