Can't think of random questions to ask friends?

I've authored a ton of articles about what interesting questions can strike a good conversation among people you know. And I can give you some tips on getting to know the people close to you better.

I've compiled the top questions to ask friends on this list. So get ready to make more solid pals.

Let's go!


Ultimate List Of Random Questions To Ask Friends

There is no wrong or right question in life. However, building lasting friendships requires questions that would reveal important things about the person you wish to learn about. These questions surpass asking about their favorite place, favorite holiday, a favorite song, the famous person they like or a celebrity crush, or even their favorite food. If you want to familiarize yourself with someone, you need to ask a deeply personal question, even if it comes out as a random thing.

Whether you're looking for a new friend or want to get to know someone better, these conversation starters are your key to gaining a new best friend.

Question Categories

6 Best Questions To Ask Friends For All Situations

The right question to get to know someone can inspire a good conversation. Inevitably, a boring question will result in a short and boring conversation, and no one wants to be in the middle of that. So, I've listed down conversation starters that will 100% give you an interesting conversation.

1. What do you value most in a friendship?

Friendship is different for everyone in various parts of their lives. Your high school peers might not be your friends now, and that boils down to the thing you value the most in your friendship.

2. What does friendship mean to you?

This is a great conversation starter if you're looking to nurture a new or existing friendship. Knowing how you perceive relationships among friends is crucial if you want them to stand the test of time.

3. What is the greatest accomplishment of your life?

Celebrating your mates' achievements is a great way to show them how proud you are of them. Get ready to hear a related story about this one.

4. Would you rather trade intelligence for looks or looks for intelligence?

Being inherently ungifted in intelligence and looks is not necessarily the worst thing or craziest thing that can happen to a person. Regardless, this question will trigger a nice debate.

5. What is the most embarrassing thing your parents have ever done?

Unlock your favorite childhood memory, perhaps the worst one, in a good way. Parents do have a thing for embarrassing their kids, even though most of the time, they really mean well.

6. What song was or do you want to be your first dance at your wedding?

Preparing for a wedding is a lot of people's dreams. This is a good question to start with if you want to help a friend build a romantic and personalized playlist for when they tie the knot.

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4 Hilarious Random Questions To Ask Friends When Bored

Asking your peers funny questions and them reacting by laughing out loud can be the funniest thing you'll ever see, fingers-crossed. So here are funny questions to ask friends to remind them of the good things in life.

7. Do you recall the moment you laughed the hardest in your life?

Inspire a fun conversation reminiscing about a most cherished moment in your and your friend's lives. What fun moment with another pal or family member can you recall that made you laugh out loud?

8. What's one amazing combination of foods that no one knows about except you?

Take asking about your friend's favorite food up a notch. People have their preferred food combo, and your mate definitely has something up his or her sleeve. The more unique and unthinkable, the better the food combination.

9. How long do you think you'd be okay with eating the same thing every day?

Make sure to say that this food is not just a favorite or comfort food. It should be something they are grossly obsessed about. Imagine pairing McDonald's fries with vanilla soft-serve.

10. Are there any words that annoy you for no reason that you just can't stand hearing or saying?

This random funny question can reveal the worst pet peeves your mate currently has. In my case, the word you're looking for is "moist." And I know plenty of people will agree that this word is despicable.

6 Deep Topics to Ask Friends to Get to Know Them Better

Harboring a strong relationship with the people you like involves asking deep questions, and so, you should be familiar with deep questions to ask. These deep questions to ask friends can be helpful when you want to discover things about someone on a whole new level.

11. What gives you hope?

Let's drop flirty questions and dare questions and stick to ones that uncover your friend's hidden self. For a lot of people, the thing that motivates them to look at the bright side is trivial. It's the weirdest thing how something so menial can be the thing that gives you the most hope.

12. What's your biggest fear?

Talking about your biggest fear is a huge step in learning about each other. Not everyone is comfortable in revealing their secrets, much less fears that can be seen as weaknesses. And so, only true friends would give you the honor and trust of knowing.

13. What is your biggest regret?

Sharing your regrets is a gateway to an honest friendship. For some people, their biggest regret is sharing things they're not supposed to do on social media.

14. What makes you feel unstoppable?

Celebrating each other's best parts is crucial to a long and fruitful friendship. So take note of the things you both are proud of and celebrate the milestones you'll accomplish in the future.

15. What life-changing events have you experienced?

Telling your pal about a time you got a life-changing lesson or realization is a favorite thing of a lot of individuals out there. So it's fun to share these memories with the people you wish to get closer to.

16. What's one thing you would change about yourself?

Change is inevitable in personal growth. It's the same with friendship. Talking about the things you wish to change about yourself is the first step in inviting someone to help you improve as a person.

6 Good Topics To Ask Friends Just For Fun

Want to have a fun time with your peers but can't think of anything to ask? Choose a fun question from this list to kick off your conversation.

17. Do you ever miss being a kid?

Questions that remind you of your glorious childhood life are always fun to answer. Reminiscing about the good ol' past and sharing similar experiences help build stronger and closer relationships.

18. Did you ever run away from home?

The people you meet come from all walks of life. So they have had experiences that you can't even begin to imagine. You'll be amazed at all the things they'd seen and heard.

19. Were you popular in school?

A lot of individuals look at their high school life with rose-colored lenses. "The golden days," some people call even go as far as calling it that. But it's always fun to learn about how people changed or remained the same after high school.

20. Do you know what you want to do with your life?

At some point in life, everyone has been asked what they want to be when they grow up. Ad the reality is that a lot of grown-ups don't even have an idea of what they want to do. Sometimes, more heads can help figure out the thing they want to do in their life together.

21. What thing in your life do you feel most grateful for?

Everyone has one thing that they're always thankful for. This might be a job, a friend, a loved one, or even menial things such as a pair of socks or a warm blanket. It's nice to talk about positive things in your life with someone you wish to get closer to.

22. Did you have an imaginary friend growing up?

Kids need friends to develop their social skills. In some cases, children grow up with imaginary friends that help them get through their days. The best thing about imaginary friends is that they're always there when you need them.

6 Juicy Questions About Romance And Relationship

Sharing intimate details about your "secret" life is a key indicator that you're with someone who makes you feel comfortable. Learn intimate facts about your pals by asking these juicy questions to ask friends.

23. Has anyone ever cheated on you?

Being cheated on is one of the worst things anybody can experience. No one stays the same after being cheated on. However, you can learn plenty of lessons from being lied to, and sharing that with other people so that they won't experience the same thing is life-changing.

24. What was your worst rebound?

Finding love is a challenge, especially after heartbreak. However, more likely than not, people commit to rebounding relationships to regain confidence and find love for themselves. And more often than not, these experiences result in exciting stories to tell.

25. Who is the most toxic person in your life?

Cutting off toxic people is crucial for your well-being. There are situations, however, where you're stuck between choosing yourself over another. Despite everything, complex situations like this help build up your essence as a person.

26. When was the last time you got stood up?

Getting stood up is far more heartbreaking and humiliating than receiving a direct rejection. People who lead on others they know are interested in them are a new level of mean.

27. Have you ever had a crush on a romantic partner's friend?

Developing feelings for a close friend's paramour is negative in most people's books. If you ask anyone, this will be a glaring red flag. Hopefully, you haven't experienced this friendship and relationship-breaking situation.

28. What's the biggest lie you told a romantic partner?

People tell lies for a lot of reasons. But honesty is an important part of strengthening one's romantic entanglements with another. This daring question is most definitely intriguing.

6 Interesting Topics To Ask People In Any Situation

Random and intriguing, these are interesting questions to ask someone to know them better. Brace yourself for the deep traits and characteristics you're about to discover about your friend.

29. What secret obsession do you have that I don't know?

Everyone has something they're obsessed about but are not vocal about it. And it's always interesting to know this hidden part of them since it shows that they trust you enough to know about the thing that makes them feel excited.

30. If you could do anything for the rest of your life, what would it be?

People are made to do something, even if it's nothing at all. Find out what your friend truly desires in his or her life with this question.

31. What emotion do you experience the most?

Whether it be love, anger, happiness, or grief, everyone experiences emotions that are healthy for them. If the talk gets serious, make sure to offer your ear and listen to what your mate has to say.

32. What makes you feel super loved?

Trivial things like asking someone if they've eaten or texting them about something that reminded you of them are some ways that can make someone feel incredibly loved and appreciated.

33. What's the single best piece of advice you ever received?

The people we meet come from all walks of life with different experiences. Some, even more than others, and these individuals usually have helpful advice up their sleeves to share.

34. Which of your accomplishments are you most proud of?

As mentioned before, celebrating each other's achievements in life, whether big or small, can be a huge step in making your friendship stronger. So ready your smiles and pride for your friend, because they deserve it.

Downloadable and Printable List of Random Questions to Ask Friends

Here is a downloadable and printable jpg/pdf list of random questions to ask friends (right-clicked the image and select Save Image As...):

The Power of Conversations in Building Friendships

According to Christy Pennison, a licensed counselor, making friends is not an easy feat. Communication is one of the main foundations of a lasting friendship. Being able to talk about your experiences, beliefs, and feelings with someone who does the same without any biases is a key indicator that your friendship will last. By communicating these things about yourself, you share a part of yourself with another individual. And according to this article, this helps make a strong bond between you.

Relationships that last a lifetime come from an effort between the parties involved. It's not even necessary that you see each other often. As long as you hear from each other, your friendship will remain strong and will stand the test of time. That's what communication does, based on this NYTimes post on how to become a better friend.

And so, you need to learn how to strike up a good conversation with someone. The next segment shows you exactly how to have great communication with virtually anyone you meet. So keep on reading.

How To Have Great Conversations - 5 Helpful Tips

Want to become a better friend? These 5 helpful tips on making great conversations which can guide you on how to be a better friend.

Tip #1: Practice active listening.

Believe it or not, the key ingredient to good communication is not talking. It's listening. Listening actively to what your friend's saying means that you listen intently and willingly hear what they have to share. This way, you'll know exactly what to say in return.

Tip #2: Ask good questions.

By actively listening, you and your friend will be on the same page. And so, you'll be able to come up with good, related questions to the stories they're telling you. Asking these questions will enhance your conversations and make them more engaging.

Tip #3: Try not to repeat yourself.

As much as possible, share one thing at a time. This way, you can focus on the details of your story or topic instead of repeating the same thing over and over.

Tip #4: Don't multitask.

How can you tell if a conversation is good? Check out the people talking. Are they doing different things or are they intently engrossed in what the other person has to say? Paying attention to your friend when they're speaking will encourage them to talk more.

Tip #5: Don't equate your experience with theirs.

People make the mistake of comparing experiences when the person they're talking to even though the other individual only wants a listening ear. So when speaking to someone, try to notice the goal of the conversation. Do they want advice? Do they want someone to listen? Don't try to add unnecessary components to the conversation.

Frequently Asked Questions

Find out how to be a pro at random questions. I'll share the answers to the most asked questions about it here.

What makes a good random question?

A good random question becomes good if it's genuine. Ask it in a way that shows total interest. This way, the person you're talking to is more lenient to answering it for you.

Are there any questions I shouldn't ask?

Yes, some questions should be reserved for times when they're more appropriate. For example, asking someone about a taboo or a touchy topic for them can be off-putting.

Is asking random questions a good icebreaker?

Yes. Random questions are incredible icebreakers to ask anyone you meet. How else would you know if both your brains operate on the same wavelength?

How do you drive a conversation with intriguing questions?

Interesting questions are nothing without the steps mentioned in the last part. Driving a conversation starts with active listening and the positive bouncing of ideas between two or more speakers.

More Awesome Articles To Explore

Have more ideas in mind? Perhaps these related posts can guide you to discovery.

  1. Like someone? Here's a guide on how you can tell if a guy likes you before you make the first move.
  2. If you're curious about how the brain falls in love. This is a helpful read to get started.
  3. A ton of people don't know how to be romantic. But this post will show you exactly how.
  4. Want to be a good friend? Find out how to make someone feel better here.

In Conclusion

Hopefully, you can create lasting friendships and more with these random questions to ask friends. It's not that hard to create new friendships and relationships if you're willing to share things about yourself and listen to what others have to share in return.

Keep close friends closer, and you're in for a friendship that'll last a lifetime.