Meaningful Questions To Ask Your Friends

At Vertellis, we believe meaningful questions to ask your friends go beyond “How are you doing today?” or “What did you do last weekend?” 

Don’t get us wrong, these types of questions are fine to ask your friend at the beginning of your meet-up or phone call, but if you’re looking to deepen your friendships, the questions you ask your friends need to be a little more juicy. 

If you feel intimidated by asking them or can’t think of any good questions to ask your friends on the spot - don’t worry! At Vertellis, funny questions are our specialty, and today we’re passing our knowledge along to you.

Keep reading for 45 personal questions to ask your friends! We’ve included special ones to ask your best friend or the new friends that you’ve made. 

Questions to Ask Your Friends

At Vertellis, we differentiate ourselves by asking our friends and family the right questions. Which is obvious, not every new friend will be as keen to share their most inner thoughts with you. That’s why we’ve divided them into 3 topics: questions to ask a new friend, questions to ask a good friend, and questions to ask a best friend. We’re very curious which one works best for you!

Questions to ask a new friend

• What activities bring you the most joy?
• What’s on your bucket list?
• If money didn’t matter, what would you do for work?
• What’s the best vacation you ever went on?
• Who are you closest to within your family?
• What’s something that scares you in life?
• What’s a cause that you’re passionate about?
• What’s your favorite childhood memory?
• What’s something challenging that you’ve overcome this year?
• What book has impacted you the most?
• What was the last movie that made you cry?
• Do you prefer the city or the country?
• What are you most looking forward to in the next year?
• If you could travel anywhere, where would you go?
• What was your best purchase this year under $100?

These questions are a great balance of learning about someone’s interests and what lights them up, combined with building trust through vulnerability. Our recommendation? Start with some of the ‘lighter’ questions and then go deeper as the conversation progresses.

Questions to ask a good friend

• What’s your biggest regret?
• What does friendship mean to you?
• Where do you need support in your life right now?
• What’s the best gift you’ve ever received?
• What are you most proud of in your life?
• What’s the biggest challenge you’ve faced in the last year?
• What do you consider your biggest strength?
• What’s your most embarrassing moment?
• How do you like to be comforted when you’re sad?
• What’s something you’ve learned about yourself this year?
• If you could change something about yourself, what would it be?
• Are you happy with your career right now?
• What’s your biggest fear?
• If you could, would you go back in time and change anything? If so, what?
• What’s something you’ve done that was scary, but you persevered?

See how these questions are a bit more personal and require more vulnerability to answer? Since you’ve already established trust with this friend, these questions help you learn even more about this person and connect on a deeper level.

Questions to ask a best friend

• What would you like people to say at your funeral?
• What would you do if you were told you had six months to live?
• What do you consider your biggest failure and what did you learn from it?
• If we planned a vacation together, where would you want to go and what would we do?
• How can I be an even better friend to you?
• What’s the biggest lie you ever told?
• Have you ever given up on a dream?
• What’s the best advice you ever received? How about the worst?
• What’s something I don’t know about you?
• How do you feel about growing older?
• What would you be willing to give up or sacrifice to achieve your dreams?
• How has your relationship with your parents changed over the years?
• Is there a question you want to ask me but haven’t because you’re afraid of the answer?
• What’s your happiest moment?
• How will you know you’ve led a meaningful life?

Best friends are perfect for personal questions

This is where you can pull out all the stops and ask the really juicy, personal questions. And let me tell you, when we talk about challenging topics like failure - this is where we reeeeally get to learn about someone. This is where the good stuff is. Just make sure you’ve clearly established trust before asking some of these!

These questions are a great balance of learning about someone’s interests and what lights them up, combined with building trust through vulnerability. Our recommendation? Start with some of the ‘lighter’ questions and then go deeper as the conversation progresses.

What are the benefits of asking meaningful questions?

These questions that you can ask your friends are meant to help you connect with each other. After all, “friendship is a state of mutual trust, support, and shared affection”.

We love that definition of friendship because it hits all the key elements of why having personal questions to ask friends is so important. 

After all, asking questions helps you:

• Build trust in your friendship.
• Create intimacy (here we mean closeness, not romance).
• Learn how to best support someone.
• Show interest in someone’s life and gain empathy for what they’re going through.

We all have stories. And stories are how we learn more about one another and deepen our connections. In friendships, we exchange stories by having conversations, which more often than not, are brought about by asking meaningful questions. 

What is a good question and what makes it meaningful?

A good question makes someone think. It's not obvious and is targeted at your friend specifically. This means no standard questions, but choose something that will resonate with them.  Now, what do we mean by a meaningful question? Like we said earlier, meaningful questions go beyond the standard surface level inquiries of “How are you?” Truly great questions are those that push us to think and reflect on our lives.

(P.S. looking for romantic questions, check out our questions to ask your boyfriend or girlfriend)

With friends, we’re not looking for their social media highlight reel - we want to know what’s actually going on with them, how they experience the world, and who they truly are as individuals.

More benefits of asking your friends questions

Wait, there is more! Connecting with your friends over your quiz helps with: 

• Giving you ideas for gifts.
• Helping you plan fun activities to do or trips to take together.
• Allowing you to be a source of encouragement for each other.
• And most importantly, deepening your relationship so you two can be friends for life, even if one of you moves away or has some other big life change.

How to Get the Most out of These Questions?

Now that you have the questions, how can you create the most connection from them? We’ll give you a few tips to get the most out of the personal ones that you can ask your friend. 

1) Don’t be afraid to dig deeper

What if you’re asking your friends these meaningful questions and you get a one-word or one-sentence response? Simply say, “Tell me more” - that’s literally what ‘Vertellis’ means in Dutch!

After all, this is all about creating conversations and deepening your connection. It’s not about getting through as many questions as possible. We’re going for quality, not quantity, so don’t be afraid to ask follow-up questions. 

2) Remember to listen

When asking your friends (or anyone!) these questions, strive for compassion, not judgment. 

Truly listen to their response and remember, you may not like what you hear. That’s part of what’s amazing about great questions: you get to learn from someone who may have a different experience or viewpoint than you. 

3) Get creative with the questions

Being genuinely interested in what you’re asking is vital. Sure, we gave lots of questions to choose from, but if you’re not truly interested in any of the answers - don’t ask! 

Use these questions for inspiration, but don’t be afraid to create your own. After all, a good question is a sincere question that comes from genuine interest and curiosity. No need to think these are the only good questions out there. 

What questions here excite you? What questions can you think of? Ask them!

4) Make a game out of it!

We know, it can feel a little awkward to suddenly bust out a list of questions and start interrogating your friends. Why not make a game out of it?

To make these questions into a game, simply take the questions from above and write them out or print them on cards. When you’re with your friend(s), place the cards face down so each of you can draw a question card one at a time. The person who drew the card can be the only one that answers the question, or perhaps everyone who is “playing” can answer. There are no rules here, so feel free to create your own!

Want a little more structure or even more questions to ask? Check out the Vertellis Holiday Edition.

5) Finally, ask yourself these questions, too.

These questions to ask your friends are great for deepening your relationships and learning more about the people you care about, but don’t forget about deepening your relationship with yourself by answering these questions, too.

Write your answers out in a journal or make a pact that every question you ask a friend you will answer, too. Again, no right or wrong way to do this!

Know your audience!

The questions we’re including in this post are meant to help you connect with all of your friends on an even deeper level. However, every friendship is different, and it would be foolish to assume that you should ask the same questions to a friend you’ve known for one week as compared to a best friend you’ve known since childhood. 

Note: We’re not saying you shouldn’t ask the same questions, but like we said earlier, friendships are built on trust.

The Brene Brown Marble Jar

Ever heard of the Brené Brown marble jar? In Brené Brown’s books where she talks about trust, she often mentions a story regarding a marble jar in her daughter’s classroom. The moral of the marble jar metaphor is that trust is built slowly, over time, in small amounts. 

What does this mean in regards to asking your friends meaningful questions? Essentially, the more trust you’ve built in your friendship over time, the deeper and more personal your questions can be. Why? Because that person will feel safe being vulnerable with you. And answering questions and sharing your story with another person is a vulnerable act.

For the questions we’re sharing with you today, keep these questions (for yourself!) in mind:

• Is this a new friend?
• Is this someone you’ve known for a while but are trying to connect more deeply with?
• Or is this a best friend who knows (almost) everything about you?

None of these are set in stone (like we said, every friendship is different), but gauge the level of trust you’ve built with the person before diving in. 

Remember the Vault

Another great tip from Brené Brown. In Brené Brown’s BRAVING acronym used to describe the elements of trust, V stands for ‘The Vault’.

What does this mean? It means you don’t share information that is not yours to share. Like we said before, answering questions is vulnerable and your friends need to trust that you are keeping their answers in confidence. Now, this may not matter if you’re asking what their favorite color is (although you never know), but if you’re asking about something more personal like their relationship with their parents, that information needs to stay with you.

I’m afraid my friends won’t be into this…

I think the number one reason we don’t ask our friends meaningful questions is that we’re afraid they’re going to shut us down.

Is that a possibility? Yes. Asking a good question is vulnerable, just like answering a good question is vulnerable. Being courageous enough to ask a meaningful question means you care about your friendship and want to connect with that person in a deeper way. 

Like so many people have said before us: no risk, no reward. You never know what friends will be willing to open up and go deep with you, so don’t write someone off without giving it a try first.

Also, if a friend asks why you’re suddenly being “all serious”, be open about why you want to ask meaningful questions. Let the person know that you value their friendship, you’re genuinely curious to hear their answers, and that you hope it will bring you two closer. Remember: it’s not about interrogating anyone, it’s about creating conversation and connecting in a more meaningful way. 

Finally, if a friend is not willing to share something, number one - don’t push it. Part of building trust is respecting boundaries. Number two, it’s not always personal. They may be working through some challenges with a professional like a therapist and don’t feel comfortable sharing certain things with friends right now. Or perhaps you two are still establishing trust in your friendship, which is both natural and healthy. 

So don’t sweat it. And don’t let one setback stop you from asking other friends meaningful questions!

Want more questions to ask your friends?

We hope these questions provide more meaning and value to your friendships of all kinds. For more questions to ask your friends, be sure to check out this blog: 20 funny questions to ask your friends.