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45 Deep Questions To Ask Friends - The Best Ways To Know Them Better

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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by | | May 19, 2021


I'll tell you about all the deep questions to ask friends you need to get your friendship to another level.

I've discussed all about the questions to ask your friends, but now I'm narrowing it down to the deep topics that bring interesting conversations.

Let's get to the good stuff!

Contents

11 Best Deep Questions To Ask Friends

These are our favorite questions to ask your friends. They are foolproof and will ensure that you always have meaningful conversations with your peers. It's the key to zero awkward silence and a lasting friendship. If you're on the lookout for conversation starters for a meaningful conversation, they're all here.

Here are the 11 best deep questions to ask friends:

1. What's your all-time favorite memory?

A quick trip down memory lane always makes for a good conversation starter. Memories can bring so much happiness, sadness, and every emotion you can think of. They make interesting conversations that you never want to end.

2. What embarrasses you the most, and what's been your most embarrassing moment?

Yikes! Be prepared to feel some second-hand embarrassment here. When we have a close friend that feels embarrassed, we can't help but feel the same way, too. You want to hide under the Earth and never appear for the next hundred years.

3. What makes you feel super loved?

Small acts of kindness go a long way. You might expect to hear about loved ones, but you'll be surprised at the small things that make people feel loved.

4. What do you use to cope when you're feeling uncomfortable?

Hey, we all have our coping mechanisms. Just make sure to keep yours on the healthy side. This is a deep conversation topic, so tread lightly.

5. When do you feel at your most vulnerable?

You know someone is a good friend if you allow yourself to be vulnerable around them. Going into this question will give you a meaningful conversation.

6. What emotion do you experience the most?

It's good questions like this that give us an idea about a person beyond what we see. Most people have never even thought about the answer to this question! It's the meaningful questions like this that matter and makes deeper conversations.

7. What's the nickname your friends have given you? What does it mean?

Nicknames always have an interesting background story. It seems like it's not much, but sometimes, nicknames can bring you into a deeper conversation.

8. What's the best advice you've ever been given?

Who knows, you might benefit from it too! Thoughtful questions like this always help the one who asks.

9. What do you think of best friends of the opposite sex?

Some people believe it's impossible to be friends with someone of the opposite sex. It might seem hard to escape the intimacy, but relationship questions like this always have many people on both sides.

10. How long does it take you to trust someone?

Some people take longer to open up, but when they do, it's usually for life. It's hard for people to give second chances, but it might be harder to give the first chance.

11. What's the one thing that people always misunderstand about you?

And why do you think that's the case? This one is a good question to get a better understanding of your friend.

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10 Deep Interesting Questions To Ask Friends

You should always have a few interesting questions to ask your friends lined up. How else are you going to end those awkward silences? Not only that, you're sure to start a great conversation with these.

Here are 10 interesting questions to ask friends:

12. How do you see me?

You'd be surprised by what your friends have to say about you! This is an important question that helps you achieve some interpersonal closeness.

13. Do you think you're brave?

And why? It sounds brave only, but this is also a cute question.

14. If you had to change your name, what new name would you pick?

Don't we all wish our parents had named us something else from time to time? Many have heard the lines "you don't look like your name," which made them think.

15. What annoys you the most about people?

Come on, admit it. What's the worst thing about people? We all have an answer to this! If you look at social media like Twitter and Facebook, you'll see many people answering this one!

16. What scares you the most?

The dark? Insects? Heights? We all have our little phobias. Sometimes they don't make sense, but that's how we feel.

17. Where would you like to be in five years?

An open-ended question gives a meaningful connection. Does your friend have a step-by-step action plan, or are they more of a free spirit?

18. Would you be with someone who doesn't have the same beliefs as you?

And what's the one belief you'd never compromise with? Do they look for the same beliefs in a conversation partner?

19. When have you felt the most challenged?

And what did you learn from the experience? Thought-provoking questions like this give you more than a glimpse of someone's life.

20. What's the craziest thing you've ever done, and would you do it again?

And perhaps more importantly, what made you do it? Maybe it's not their biggest regret.

21. What's your idea of a perfect vacation?

A lazy beach holiday? A wild road trip? Their favorite place would always count, but you'd be surprised by how different your friends' responses are!

7 Random Deep Questions To Ask Friends

These are the best random questions to ask your friends when they least expect them. A random question will spice the conversation up!

Here are 7 random questions to ask friends:

22. What makes you feel unstoppable?

A sweaty workout session? A genuine compliment from someone you care about? Or the most potent drug of all - being in love? It's the right question to stop the small talk.

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

Imagine not having to worry about your biggest fear. Your friend's answer can tell you a lot about them as a person.

24. Are you more afraid of death or not living?

This one is as deep as they get! There are bound to be so many opinions on this one. You can expect a long and deep conversation with something like this.

25. How would you rank the following in importance: family, career, love life?

If someone says they value their career the most, you might want to reconsider your friendship with them.

26. Did you ever judge someone for the dark secrets they told you?

And what were those secrets? Were they grateful that that certain person came to them to share those secrets?

27. What would you do if your parents didn't like your partner?

Would you go full Romeo and Juliet on them?

28. If you could do anything knowing you would not fail, what would you do?

And is it still worth doing if you were to fail? These are the kind of icebreaker questions you should be asking.

8 Deep Would You Rather Questions To Ask Friends

Don't have conversation fizzles! Would you rather questions make for the best party ice breakers, don't they? They don't need to be dirty questions. These are as wholesome as they get!

Here are 8 deep would you rather questions to ask friends:

29. Would you rather become someone else or just stay you?

And who's "you" to begin with? Can we all clearly define who we are? We should start with that.

30. Would you rather live a relaxed and tranquil life in a small cabin far from society or a stressful life in a massive house in the middle of your favorite city?

It probably depends on your age and the stage you're at in life. Even our favorite thing would change over time.

31. Would you rather never feel jealous or angry again?

The answer should be neither: both emotions are healthy in small doses. They matter even for a healthy relationship.

32. Would you rather be famous and widely mocked, or ordinary, and no one knows who you are?

You will be surprised at how people answer this. Sometimes they don't seem like the kind of person who wants to be famous, but they'll choose fame anytime.

33. Would you rather wake up alone in a boat in the middle of water or the middle of the desert?

At least the boat could take you somewhere. But let's not kid ourselves. It can be scary in the middle of the ocean.

34. Would you rather your life ended at 40, and you had absolutely no regrets or lived until 80 but died with many regrets?

If you've never allowed yourself to make mistakes, fail, and make choices you might later regret, have you ever truly lived? It's the weirdest thing about life, but that's the meaning.

35. Would you rather never be allowed to use a cell phone again, or anyone can see your entire internet history whenever they wanted (and you can't delete anything)?

Ouch. That's a tough one. Does browsing in incognito mode count?

36. Would you rather hate your job but get a great salary or love your job but get pretty lousy pay?

Do you live to work or work to live? It's a great question that everyone gets asked at some point.

9 Deep Personal Questions To Ask Friends

Do you want to get to know your friends on a deeper level? Our collection of personal questions to ask friends should help! These are generally polite conversation topics, so no need to worry!

Here are 9 deep personal questions to ask friends:

37. What do you want people to feel when they're around you?

Joy? Excitement? Peace? Whatever it is, it says a lot about the person you're asking.

38. What's a dream you've never said out loud?

Sometimes we are just too afraid to dream big. We should still hope to achieve that dream, though!

39. Is it easy for you to show yourself love or speak kindly to yourself?

Most people find it surprisingly difficult. Loving yourself is tough.

40. What's more important to you: status, power, or money?

Can money buy you power and status? This is interesting to ask because there's a lot to be said about either of the three.

41. What's the one thing you'd like to change about yourself today, and why?

Do you want to quit smoking? Start working out? Become more assertive? The only limit is your creativity.

42. Do you want kids? If so, which would you prefer: having a baby without a partner or a partner without a baby?

Guess it depends on the partner!

43. What are some things that you wished people knew about you?

And why do you think they don't know them already? Sometimes people surprise us now and then, so it makes sense.

44. What did your past relationship teach you?

The only failed relationships are the ones you learned nothing from. You don't have to be a relationship expert to know that.

45. What do you think about when you're by yourself?

Do you think about the past or daydream about the future? Or are you one of those normal ones that are alert in the present? Kidding!

Downloadable and Printable List of Deep Questions To Ask Friends

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

Frequently Asked Questions

Knowing about the right deep questions to ask your friends can leave you with more questions of your own. I'm here to answer them all.

What is the most effective way to see a person's true personality?

The best way to see a person's true personality is by spending as much time with them as you can. By spending time with them, you can ask all of your burning questions to know more about them.

Why do people ask strangers for intimate relationship advice?

Sometimes strangers are the best people to go to for advice because they have no idea of who we are. We're a clean slate to them. There's no judgment or subjective point of view.

Is it fine to ask friends controversial questions to know them better?

If one of the random questions to get to know someone that you came up with is controversial, there's a chance that your friend might not be too willing to answer. If that's the case, don't push it. If you're close with your friends, chances are they won't mind, but it's still best not to force people to answer your questions if they don't want to.

Will deep questions give you honest answers from your friends?

Asking deep personal questions is the best way to get a deeper look at your friends. You can't expect everyone to answer honestly, but you have to trust them. Whatever kind of answer they give will still say a lot about them.

How To Pick The Best Deep Questions To Ask Friends

Do you sometimes wonder if it's a good idea to ask your friend a specific "deep" question? Is the question appropriate? Would they feel hurt or offended? Sometimes, it is hard to tell!

Here is how to pick the best deep questions to ask your friends:

1. Pick Your Timing Right

If you're going to be asking deep questions, make sure to do it when the timing's right. Don't bombard people with intimate questions when they least expect it. Pick a time when your friend is fully relaxed and, ideally, in a somewhat philosophical and reflective mood.

2. Don’t Be Too Nosy

If your gut feeling tells you that a question might be a bit too personal, it's best to err on the side of caution and not ask it. If your friend wants to share that particular piece of information with you, they will do so when they feel comfortable doing it.

3. Be Mindful of Who Else Is There

Don't put your friends on the spot by asking them deep questions they might not want to answer in front of other people. It might embarrass them.

More Best Questions To Ask

How about some more great questions to ask? It's always helpful to have some ready.

  1. Start by reading our fun questions to ask your friends.
  2. Next, check out our selection of funny questions.
  3. Finally, take a look at these interesting questions to ask a guy.

In Conclusion

Did you enjoy our selection of deep questions to ask your friends? If you use them at the right time and in the right place, you will get to know your friends on a much deeper level. The trick is always to have one or two deep questions to ask friends up your sleeve!

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