Ask Questions That Go Deeper
Thirty-two questions that go deeper, because better questions are the shortcut to closer friendship.
Good questions are a gift. Depth comes from curiosity, not from pressure.
31 tips that really help
These ideas come from Platonic (Marisa Franco), Friendship (Lydia Denworth), Friends (Robin Dunbar), and everyday practice. Pick one tip and try it today.
Why deeper questions work
Psychologist Arthur Aron found that mutual self-disclosure through increasingly personal questions builds closeness quickly. Good questions skip the small talk.
Try one this week.
Ask about meaning
What gives your work meaning? invites values. People enjoy being asked.
Ask it.
Ask about dreams
What would you love to do in the next five years? invites hope. It reveals direction.
Ask it.
Ask about pride
What are you proud of lately? invites joy and invites the story.
Ask it.
Ask about challenges
What has been the hardest thing this year? invites support. Ask gently.
Ask with warmth.
Ask about influences
Who shaped you the most? opens history. People love to credit mentors.
Ask it.
Ask about joy
What makes you lose track of time? finds passions. Delightful.
Ask it.
Ask about regrets and lessons
What is something you learned the hard way? invites wisdom. Choose trusted settings.
Ask carefully.
Ask about the future
What are you looking forward to? invites anticipation. Light and deep.
Ask it.
Ask about values
What do you wish more people understood? is thoughtful.
Ask it.
Ask for a story
Can you tell me about a moment that changed you? invites narrative.
Ask it.
Follow with why or how
After an answer, ask what made it so? Deepen.
Add one.
Use the thirty-six questions
Aron’s questions are a famous list. Try a few with a friend.
Look them up.
Script: the opener
Can I ask you something a bit different? Light.
Use it.
Script: the dream
If you could do anything for a year, what would it be? Playful.
Use it.
Script: the meaning
What part of your life feels most meaningful right now? Sincere.
Use it.
Script: the share
My answer is this, and I have been thinking about it lately. Reciprocal.
Use it.
Mistake: interrogating
Too many deep questions feel like a test. Share too.
Balance.
Troubleshoot: when they deflect
Respect it and ask lighter. No pressure.
Lighten.
Troubleshoot: when it feels awkward
Frame it as a game. Humour helps.
Make it playful.
Troubleshoot: when you run out of ideas
Keep a list in your notes. Ready.
Save five.
Troubleshoot: when they cry
Stay present and kind. Offer tissues and time.
Be gentle.
Troubleshoot: when time is short
Ask one question and give it space. Quality.
Ask one.
Drill: a long walk
Use a walk for deeper talk. Easy.
Plan it.
Ask about what they care about
Questions like, what do you love about your work? open a deeper level of chat.
Ask what matters.
Use the follow-up why
After an answer, ask gently, what made you choose that? because why leads to real stories.
Ask why.
Share your own answer too
Answer your own question honestly so the chat feels two-way and safe.
Share back.
Mistake: asking too many personal questions at once
A stream of questions feels like an interview, so mix questions with comments.
Mix it up.
Troubleshoot: when they give short answers
Slow down and offer something about yourself first, because it makes sharing feel safer.
Share first.
Drill: write five deeper questions
Write five kind, deeper questions and use one in your next conversation.
Write them.
Drill: remember one answer
Remember one thing they said and ask about it next time, to show you listened.
Remember it.
Easy things to say
When you are stuck, pick one of these. They work in many everyday friendships.
“What has been on your mind lately?”
“What would your perfect day look like?”
“What are you proud of this year?”
“What matters most to you right now?”
“Thanks for sharing that.”
“I love learning how you see things.”
Your first week
One small action a day. Each day is only a little bigger than the last.
Pick three deeper questions
Ask one over coffee
Listen without fixing
Share your own answer
Follow with a why or how
Thank them
Note what you learned
Further reading
- Platonic (Marisa Franco)
- Friendship (Lydia Denworth)
- Friends (Robin Dunbar)
The tips above are written in our own words and are general guidance. The books are suggestions for further reading.
More lessons in “How to Turn an Acquaintance Into a Friend”
Keep going. Small steps every day make a big change.
← Previous: The Power of Small VulnerabilitiesNext: Share Your Real Opinions →
- The Rule of Repeated Contact
- Friendship Takes Around Fifty Hours
- Why Small Moments Matter Most
- Proximity, Repetition and Shared Experience
- Weak Ties Can Become Strong Ties
- Why Most Friendships Stall
- What Makes Someone Click With You
- The Low-Pressure Invite
- Invite for Coffee, Not for a Commitment
- Suggest Something You Both Mentioned
- Offer Two Options Instead of One
- Text the Invitation Naturally
- Handle a Maybe or a No Gracefully
- Be the One Who Suggests Plans
- Do an Activity Instead of Just Talking
- Try a New Thing Together
- Cook or Eat Together
- Walks and Outings That Bond
- Attend an Event Together
- Make a Small Tradition
- Help Each Other With Something Real
- Share a Little More Each Time
- The Power of Small Vulnerabilities
- Ask Questions That Go Deeper
- Share Your Real Opinions
- Trade Stories, Not Just Facts
- Say "Me Too" With Care
- Let Them See You Imperfect
- Meet Their Other Friends
- Introduce Them to Yours
- Remember Their Important Dates
- Check In During Tough Times
- Celebrate Their Wins
- Show Up When It Counts
- Say Out Loud That You Enjoy Their Company
- Become Each Other's Go-To Person
- Give Each Other a Nickname or a Ritual
- Be Patient: Closeness Cannot Be Rushed
- Know When a Friendship Is Not Taking Off
- Your Friendship Growth Plan
