You have a friend you would call close. You could list her job situation, the thing with her sister, the sentence she said in the car last October that you still think about. Now guess what she has been carrying for the last three weeks. Most of us would miss.
That gap between how well we think we know our people and how well we do is one of the better documented findings in social psychology, and it has a fix that takes about four seconds. You ask.
Trying Harder to Understand Someone Does Not Work
The standard advice is to put yourself in the other person’s shoes. Tal Eyal, Mary Steffel, and Nicholas Epley ran twenty-five experiments testing whether that instruction improves accuracy when predicting another person’s thoughts, feelings, and attitudes. It did not. Perspective taking showed no consistent benefit, and if anything it lowered accuracy overall while raising people’s confidence in their judgments.
Confidence went up. Accuracy did not. That combination is the whole problem with self-assessed empathy, and it explains why the people who describe themselves as the most intuitive readers of others are frequently working from a script they wrote themselves.
What did improve accuracy in that research was getting information directly from the person instead of simulating them internally. Asking outperformed imagining.
Closeness Makes the Problem Worse
You would assume the effect shrinks with familiarity. It grows.
Kenneth Savitsky, Boaz Keysar, Nicholas Epley, and colleagues found what they named the closeness-communication bias. Participants following instructions from a friend made more egocentric errors than those following a stranger, and when people tried to convey specific meanings through ambiguous phrases, they overestimated how well they had been understood more with a friend or spouse than with a stranger. The explanation the authors give is that we actively monitor a stranger’s different perspective because we know we have to, and we let that monitoring go with people we are close to.
With a new coworker you explain the backstory. With your oldest friend you say “the thing with my mom” and assume it landed. Sometimes it does. Often you are both nodding at different pictures.
Asking Questions Works Better Than Almost Anyone Expects
Karen Huang and a team at Harvard studied question-asking across three studies of live conversations. People who asked more questions, and follow-up questions in particular, were better liked by their conversation partners, and the effect ran through perceived responsiveness, which covers listening, understanding, validation, and care. Despite how consistent the effect was, people did not anticipate that asking more questions would change how others saw them.
The follow-up question is the operative unit here. Not a new question. The second question about the thing they already said.
The Awkwardness You Are Bracing For Usually Does Not Arrive
The reason most of us stay on the weather-and-work loop is that we expect the deeper version to be uncomfortable. Michael Kardas, Amit Kumar, and Nicholas Epley tested that expectation directly. Deep conversations felt less awkward and produced more connectedness and happiness than participants predicted, people were especially likely to overestimate the awkwardness of deep conversations compared with shallow ones, and after having both kinds, they felt closer to their deep conversation partners. The gap came from participants expecting others to care less about what they disclosed than those others did.
There is a companion finding worth holding onto. Erica Boothby and colleagues documented the liking gap, where people systematically underestimate how much their conversation partners liked them and enjoyed their company after an interaction. So the person you think you are bothering is, on average, having a better time than you think.
How to Ask a Better Question
Ask the second question. The first answer to any question is a status report. “Work is busy.” The second question is where the information lives. “Busy in a good way or the other way?” This is the move Huang’s research isolated, and it costs nothing.
Ask about the specific instead of the general. “How are you” invites a summary, and summaries are where people hide. “What did Tuesday look like” invites a scene. Scenes have detail in them, and detail is what you were missing.
Say your read out loud and let them correct it. Instead of concluding privately that your friend is upset about the promotion, tell her that is what you think and give her room to say no. Closeness bias survives on unverified guesses. Speaking the guess kills it.
Ask before you advise. Advice ends the conversation because it signals you have finished gathering. If you want the rest of what they know, hold the fix and ask one more thing.
Ask in writing when speaking is not working. Some people freeze when a question arrives with a face attached to it and answer beautifully when the same question shows up on a screen and they have a day to sit with it. This is the same reason our post on staying connected with grandparents who aren’t on social media argues for meeting people in whatever format they already use.
Ask the same question again in a year. Answers move. A question you asked in March and again the following March gives you a record of somebody changing, which is a thing almost nobody keeps.
Deep Questions to Ask Friends
These work best one at a time in an ordinary moment rather than delivered as a set.
Questions That Get Past the Update
- What has been taking up the most space in your head this month?
- What is something you have been putting off, and what is it about?
- What is going well that you have not told anyone about?
- What is the hardest part of your week that has nothing to do with work?
- What are you tired of explaining to people?
- When was the last time you felt like yourself?
- What would you do with a free weekend if nobody found out?
- What is something you changed your mind about recently?
Questions About Where They Came From
- Who were you at nineteen, and what would that person think of you now?
- What is a story from your family that gets told wrong?
- What did you want to be before you knew what jobs were?
- Which friendship from your past do you still think about?
- What is the best decision you made that looked like a bad one?
- What did your parents worry about that you now understand?
- What is a place you would go back to if you could?
Questions About You and Them
- When did you decide we were friends?
- What do I get wrong about you?
- Is there something you have wanted to tell me and have not?
- What do you need from me that you have never asked for?
- What is something I do that you find funny?
- When have I let you down without knowing it?
- What would make it easier to reach me when you need to?
Questions for a Friend Going Through Something
- Do you want help thinking about it or do you want me to listen?
- What is the part nobody is asking about?
- What has been surprisingly fine?
- Who else knows, and how has that gone?
- What would a good outcome look like from here?
- What do you need this week specifically?
If the person you want to ask lives far away, our post on staying close with adult siblings who live far away covers how to keep a thread running without a group chat nobody opens.
Better Questions Still Need Repetition
One good conversation does not make a close friend. Jeffrey Hall, at the University of Kansas, tracked how friendship status changed with time spent together. Moving from acquaintance to casual friend took roughly fifty hours of interaction, casual friend to friend around ninety more, and best friend more than two hundred hours. Hours together predicted closeness, and time spent in leisure activities predicted it too.
The questions change what happens inside those hours. The hours still have to happen. There is a reason the rhythm of family check-ins tends to beat the intensity of any single one.
Arthur Aron’s closeness procedure, the study behind the famous thirty-six questions, worked on the same principle. Escalating mutual disclosure between two strangers, over forty-five minutes, produced measurable closeness. The mechanism was structure. Somebody supplied the questions so neither person had to invent them under pressure.
Frequently Asked Questions
Is Empathy Something You Can Improve?
Yes, though probably not through effort alone. The evidence suggests that trying harder to imagine another person’s experience does not make your guesses more accurate. Gathering information from them does. Improving means asking more and assuming less.
How Do You Ask a Deep Question Without Making It Weird?
Ask one, in the middle of something else, and then drop it if it does not land. Weirdness comes from announcing the intention, since “I want us to be closer” puts the other person on a stage. A single unannounced question in the car does not.
What If Someone Never Opens Up?
Change the subject rather than the pressure. People who deflect on feelings often talk at length about work they are proud of, a place they lived, or something they collect, and the personal material tends to arrive through the side door. Written questions also help people who freeze in conversation.
How Often Should You Ask Deep Questions?
Once a week is a sustainable rhythm and one that most friendships can carry without strain. Daily is interrogation. Once a year is a birthday card.
Do These Questions Work Over Text?
They do, and for some people they work better. Asynchronous questions give the answerer time to think rather than three seconds to perform, which usually produces a longer and more careful answer.
Studies Cited in This Post
- Eyal, T., Steffel, M., & Epley, N. (2018). Perspective mistaking: Accurately understanding the mind of another requires getting perspective, not taking perspective. Journal of Personality and Social Psychology, 114(4), 547-571.
- Savitsky, K., Keysar, B., Epley, N., Carter, T. J., & Swanson, A. (2011). The closeness-communication bias: Increased egocentrism among friends versus strangers. Journal of Experimental Social Psychology, 47(1), 269-273.
- Huang, K., Yeomans, M., Brooks, A. W., Minson, J., & Gino, F. (2017). It doesn’t hurt to ask: Question-asking increases liking. Journal of Personality and Social Psychology, 113(3), 430-452.
- Kardas, M., Kumar, A., & Epley, N. (2022). Overly shallow? Miscalibrated expectations create a barrier to deeper conversation. Journal of Personality and Social Psychology, 122(3), 367-398.
- Boothby, E. J., Cooney, G., Sandstrom, G. M., & Clark, M. S. (2018). The liking gap in conversations: Do people like us more than we think? Psychological Science, 29(11), 1742-1756.
- Hall, J. A. (2019). How many hours does it take to make a friend? Journal of Social and Personal Relationships, 36(4), 1278-1296.
- Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness. Personality and Social Psychology Bulletin, 23(4), 363-377.
Start With One Question This Week
Pick one from the list and ask it the next time you talk to someone. Then ask the follow-up. That is the entire method.
If remembering to ask is the part that never happens, that is the job nosy does. One question a week goes out to your circle, everyone answers on their own time, and the answers open together. Nobody has to be the person who starts.
Start your circle free and find out what you have been guessing about.