Transform casual chats into genuine connections with these 12 questions to ask a friend. From lighthearted inquiries to deep “get to know you” questions, each conversation starter has been carefully selected to strengthen your friendships and create lasting bonds.
What’s Coming Up
- Starting Meaningful Conversations with Friends
- Questions to Ask a Friend to Understand Their Past
- Questions About Present Life and Values
- Questions About Dreams for the Future
- Good Questions That Build Deeper Trust
- Understanding Friends Better
- Making Every Conversation Count
- Frequently Asked Questions
- Further Reading
Starting Meaningful Conversations with Friends
We’ve all been there – sitting across from a close friend, wanting to connect more deeply, but somehow falling into the same old small talk.
Maybe the two of you are grabbing coffee, taking a walk, or just hanging out. You know that there’s so much more to discover about each other, but the usual questions just lead to the usual answers.
What if you could turn these everyday moments into opportunities for real connection?
Think about your closest friendships. Chances are they became close because you moved past surface-level chatter and started sharing your real thoughts, dreams, and experiences.
Every true friendship has the potential for that kind of depth – sometimes we just need the right questions to unlock it.
This article explores 12 meaningful questions that can help you move beyond small talk to strengthen any kind of friendship. You might be:
- Wondering how to make friends
- Reconnecting with someone after growing apart
- Hoping to go beyond surface-level chat with an acquaintance
While basic conversation starters help break the ice, these questions dig deeper. They create space for genuine sharing and understanding between friends. Ready to transform your next friendly chat into something more meaningful? Let’s explore how to do just that.
Ready to uncover the truth about who you really are? Take our free personality test and gain deep insights into your strengths, challenges, and more in just 10 minutes.
Questions to Ask a Friend to Understand Their Past
Your friends are walking stories – full of plot twists, life-changing moments, and experiences that made them who they are today.
Sure, you might know their current favorite song or their biggest pet peeves, but what about the life events that shaped their dreams or the advice that redirected their path?
The following questions to ask a friend can unlock those stories.
What’s your favorite childhood memory?
People tend to have that one golden childhood memory that still makes them smile. It might be something tiny – like catching fireflies on summer nights – or something huge, like the day their little sister was born.
Whatever story someone chooses to share in response to this question usually hints at what truly matters to them, even now.
What’s the best piece of advice that you’ve ever received?
Behind every piece of wisdom is usually an interesting story. Did it come from a random stranger on a bus? Your friend’s grandmother? That teacher who saw their potential?
Letting your friend fill in these details will often reveal both a pivotal moment and the people who influenced their path.
What experience has shaped you the most?
This question might uncover anything from a life-changing travel adventure to the summer someone learned to stand up for themselves. It’s an invitation to share transformative moments of challenge, triumph, or unexpected discovery.
Pro tip: When discussing the past, remember that not all memories are happy ones. If your friend seems hesitant or uncomfortable, gently shift to a lighter topic if they do not want to go there. Sometimes simply saying “We can talk about something else if you’d prefer” can help maintain trust and keep the conversation flowing naturally.
Questions About Present Life and Values
These deep “get to know you” questions dive into what matters right now – the dreams that someone’s chasing, the values that they’re living by, and the real stuff that is happening beneath their social media highlights.
What makes you feel most alive?
Everyone has those moments when they feel completely in their element. Maybe it’s while painting at 2 a.m., hiking to a summit, or teaching someone a new skill.
This question often reveals what passions someone might not talk about in their day-to-day life – or sometimes even dreams that they’ve put on hold.
What do you value most in life?
Instead of asking about someone’s surface-level preferences or their latest celebrity crush, this question invites them to share their core beliefs.
Their answer might be surprising – sometimes the friend who seems focused on career success actually values family time above all, or the social butterfly might treasure their quiet moments of solitude the most.
What’s your biggest challenge right now?
This question cuts through the “Everything’s fine” facade that often gets presented to the world. It gives people permission to be real about their struggles, whether those include a bad habit that they’re trying to break or a bigger life transition.
Pro tip: These questions to ask a friend work best when you’re willing to share too. After your friend answers, offer your own thoughts. This back-and-forth creates a natural rhythm of sharing, and your honest answers will show your friend that you trust them too.
Questions About Dreams for the Future
Our dreams have a way of revealing who we are.
These top questions to ask someone about their hopes and dreams for the future can transform a regular chat into an inspiring exchange of possibilities. More revealing than discussing someone’s perfect day or guilty pleasures, these conversations uncover what truly matters.
What’s one goal that you’re working toward?
This deep question reveals what your friend values enough to actively pursue right now. It moves past vague “maybe someday” dreams into the real, messy territory of current ambitions. Understanding their active goals gives you insight into their priorities and creates natural opportunities to support their journey.
What would you do if you couldn’t fail?
By removing the constraints of reality, this question creates space for sharing those buried dreams – the ones that feel too big or too scary to say out loud. Beyond typical bucket list items, the answer will often unveil your friend’s truest aspirations, uncovering passionate desires that they might normally keep hidden.
What adventure would you like to experience in the next 5 years?
The word “adventure” means something different to everyone. Your friend’s answer reveals not just a future plan but also their personal definition of what makes life thrilling. It’s a window into how they imagine their best life unfolding.
Pro tip: When discussing dreams for the future, resist the urge to problem-solve or point out obstacles. These questions to ask a friend work best when you simply listen and encourage. There’s plenty of time for practical planning later – this moment is for dreaming big.
Good Questions That Build Deeper Trust
Sometimes the most meaningful things remain unsaid, hidden beneath layers of everyday conversation. These questions to ask to get to know someone create moments of genuine vulnerability where friends can share the thoughts and feelings that they usually keep private.
What’s one thing that you wish more people understood about you?
This question invites people to share how they want to be seen, beyond surface impressions or misunderstandings. Their answer often reveals the gap between how they present themselves to the world and how they truly feel inside, offering a chance to understand them more completely.
What’s something that you’ve always wanted to tell me but haven’t?
By explicitly creating space for unspoken thoughts, this question acknowledges that even close friends sometimes hold back. It opens the door for sharing anything from deep appreciation to gentle feedback, strengthening trust through honesty.
What makes you feel safe enough to be vulnerable with someone?
This question uncovers someone’s personal definition of emotional safety. Understanding what helps them feel secure enough to open up provides valuable insights for building stronger trust in your friendship.
Pro tip: Timing matters with these deeper questions. Choose private spaces where you won’t be interrupted, and avoid these topics when either of you feels rushed or distracted. True vulnerability needs space to breathe.
Understanding Friends Better
When it comes to asking meaningful questions and sharing honest answers with a friend, your personality types play a fascinating role in how each of you might approach these conversations. Two particular personality dimensions influence how we engage in deeper discussions.
First, whether we are Intuitive or Observant affects how we process information from the world around us. Intuitive personalities naturally get lost in their imagination and future possibilities, while Observant types focus more on what is right in front of them.
This explains why, according to our research, 91% of Intuitive personalities say they enjoy discussing different views and theories on what the future could look like, compared to just 53% of Observant types. Intuitive types are more likely to get lost in different possibilities. Meanwhile, Observant friends might prefer concrete, practical discussions focused on tangible outcomes.
Neither approach is better. They’re just different ways of interpreting information.
How we discuss deep questions is also influenced by whether we have the Thinking or Feeling personality trait. Thinking types rely more heavily on rational analysis, while Feeling types trust emotional intelligence and human impact to guide them.
For example, 65% of personalities with the Feeling trait say they mostly listen to their heart when making important choices, compared to just 7% of those with the Thinking trait.
Neither approach is right or wrong. They’re simply different paths to reaching decisions and will likely impact how someone responds to these 12 questions to ask a friend.
Keep in mind: These personality preferences are not either/or categories that you will always fit into. Think of them as subtle tendencies rather than absolutes.
Making Every Conversation Count
Every friend approaches conversation differently. Some people light up during abstract discussions, while others thrive in practical exchanges. Some process things through feelings, others through analysis.
While these differences might seem like barriers at first, they’re actually opportunities for deeper understanding. Whether you’re asking questions or sharing answers, knowing these various styles – including your own – can transform how you connect with friends. Find out more by exploring 16Personalities further and taking our free personality test.
Frequently Asked Questions
What are good questions to ask a friend?
Good questions to ask a friend should create opportunities for meaningful sharing and help you discover new aspects of their personality, values, and experiences. The best questions for a friend balance curiosity with respect while creating space for connection.
What questions can help strengthen a friendship?
Questions that strengthen friendships include those about personal values, shared memories, and future aspirations. Asking about goals that your friend is working toward, what makes them feel safe, or their favorite childhood memories creates vulnerability and trust that builds stronger bonds.
How can I get to know my friend better through questions?
Get to know your friend better by asking about their past memories, current preferences, and future aspirations. Their answers can reveal their priorities, boundaries, and values, giving you deeper insight into who they truly are beyond surface-level conversations.