7.1 The Art of Questions

Here’s a counterintuitive truth about conversations: the person asking questions is usually more liked than the person giving impressive answers.

We spend so much energy crafting witty responses, preparing interesting stories, and polishing our self-presentation. But research shows we’re optimizing the wrong thing. The single most effective conversational behavior for building attraction isn’t what you say about yourself—it’s how you inquire about others.

The Question-Asking Effect

A landmark study by Harvard researchers examined what makes people likable in conversations.^[1] Across multiple experiments—including analysis of online conversations and real speed-dating interactions—they found a consistent pattern:

People who ask more questions are better liked.

This wasn’t a small effect. In speed-dating contexts, people who asked more questions were significantly more likely to secure second dates. The researchers could predict dating success based on question-asking behavior alone.

But here’s what makes this finding remarkable: people don’t realize this. When participants were asked what behaviors would make them more likable, they didn’t mention question-asking. We systematically underestimate how much others appreciate being asked about themselves.

Why does this work? Questions signal something powerful: responsiveness. When you ask questions, you demonstrate that you’re listening, that you care about understanding the other person, and that you find them interesting enough to learn more about.

Not All Questions Are Equal

The same research revealed that question type matters enormously.^[2]

There are essentially three types of conversational questions:

1. Introductory Questions

“What do you do?” “Where are you from?”

These are necessary for getting conversations started but don’t build much connection on their own. They’re the conversational equivalent of a handshake—expected, functional, forgettable.

2. Mirror Questions

“What about you?” “How about yourself?”

These bounce the same topic back without advancing the conversation. They show minimal engagement—you’re just waiting for your turn to talk about the same thing.

3. Follow-Up Questions

“What made you choose that career?” “How did that feel when it happened?”

Follow-up questions are where the magic happens.

The research found that the boost in likability specifically came from follow-up questions, not introductory or mirror questions.^[2] Follow-up questions require you to actually process what the other person said and respond to their specific content. They prove you were listening.

A follow-up question says: What you just said was interesting enough that I want to know more.

Open vs. Closed Questions

Beyond question type, question structure matters too.

Closed questions have limited answers: “Did you like it?” “Is that your favorite?” “Have you been there before?”

Open questions invite elaboration: “What was that like?” “How did you end up doing that?” “What made you interested in that?”

Research on conversational dynamics found that asking more open questions and fewer closed questions leads to deeper engagement.^[3] Open-ended questions encourage people to share their thoughts, feelings, and experiences in their own words.

The difference in practice:

Closed	Open
”Did you have a good weekend?"	"What did you get up to this weekend?"
"Do you like your job?"	"What’s the most interesting part of your work?"
"Is that your family?"	"Tell me about your family.”

Closed questions feel like checkboxes. Open questions feel like invitations.

The Self-Disclosure Connection

Why do questions work so well? Part of the answer lies in what questions produce: self-disclosure.

A meta-analysis of 94 studies confirmed what social psychologists have long suspected: people who engage in intimate self-disclosure are liked more.^[4] The relationship is robust and bidirectional—we disclose more to people we like, and we like people more after disclosing to them.

Here’s the key insight: when you ask good questions, you’re creating opportunities for the other person to self-disclose. Self-disclosure is inherently enjoyable—people like talking about themselves. And they attribute that enjoyment to you, the person who made it possible.

You become associated with how good they felt during the conversation—even though you weren’t the one doing most of the talking.

Curiosity as Connection

There’s something deeper going on here than conversational technique. Question-asking reflects genuine curiosity, and curiosity itself predicts relationship outcomes.

A study on intimacy development found that people high in trait curiosity were rated as more attractive by their conversation partners.^[5] During reciprocal self-disclosure exercises—the kind that naturally build closeness—curious people formed stronger connections.

This suggests that question-asking works best when it reflects real interest, not tactical maneuvering. People can usually sense the difference between genuine curiosity and going through the motions.

The good news: curiosity can be cultivated. When you approach conversations with the mindset that everyone has something interesting to teach you, questions flow naturally.

Avoiding Interrogation Mode

There’s an important caveat: question-asking can go wrong.

Rapid-fire questions without corresponding self-disclosure creates an interrogation dynamic, not a conversation. Research on conversational balance shows that the disclosure-liking effect operates as a “dynamic interpersonal system”^[4]—both parties need to share for connection to build.

The pattern should be:

Ask an open question
Listen actively to the response
Follow up with related questions or reflections
Share something relevant about yourself when natural
Return to asking about them

The ratio matters less than the rhythm. Conversations should feel like tennis rallies, not job interviews.

Signs you’ve tipped into interrogation:

The other person’s answers are getting shorter
They’re not asking anything back
You can’t remember anything they’ve said because you’re planning your next question
They look uncomfortable or cornered

If you notice these, shift gears: share something about yourself, make an observation, or let comfortable silence happen.

High-Quality Listening

Questions are only half the equation. How you receive the answers matters just as much.

Research on listening and responsiveness found that high-quality listening—paying attention, comprehending what’s being said, and maintaining a non-judgmental position—promotes the very responsiveness that makes people feel connected.^[6]

High-quality listening involves:

Attention signals: Eye contact, nodding, leaning in slightly. These non-verbal cues communicate that you’re present and engaged.

Comprehension confirmation: Brief verbal acknowledgments (“Right,” “I see,” “That makes sense”) that show you’re tracking without interrupting.

Non-judgment: Not evaluating or immediately offering opinions. Letting them finish their thought completely before responding.

Remembering and returning: Bringing up something they mentioned earlier shows you were actually listening, not just waiting to talk.

Poor listening undermines even the best questions. If you ask “What was that like?” but then check your phone while they answer, you’ve negated the benefit.

The Speed-Dating Evidence

Some of the most compelling research on question-asking comes from speed-dating studies, which compress relationship formation into observable, analyzable interactions.

Beyond the Harvard research, studies using eye-tracking during speed dates found that engagement behaviors—including attentive listening and responsive interaction—predicted mutual attraction and second-date requests.^[7]

What these studies reveal is that early conversation patterns matter enormously. First impressions aren’t just about appearance or confidence—they’re about how you make the other person feel through your conversational behavior.

The people who succeed in these condensed interactions aren’t the ones with the best stories or the most impressive credentials. They’re the ones who make their partners feel interesting, heard, and valued.

And the primary tool for doing that? Questions.

Practical Application

Here’s how to improve your question-asking starting today:

Before conversations

Adopt a curiosity mindset: “What can I learn from this person?”
Prepare one or two good open questions as backup, but don’t script
Remind yourself that asking > telling when building connection

During conversations

Aim for follow-up questions over introductory questions
Use open questions more than closed ones
Listen for details that invite deeper exploration
Notice when you’re planning your response instead of listening
Share about yourself too—aim for conversation, not interrogation

After conversations

Reflect: Did you learn something new about them?
Notice: Did the conversation feel balanced?
Remember: Something they said for next time

Questions that build connection

Instead of: “What do you do?” Try: “What got you into [their field]?” or “What’s the most interesting thing you’re working on?”

Instead of: “Do you like living here?” Try: “What’s your favorite thing about this city?” or “How did you end up here?”

Instead of: “That’s cool.” Try: “What was that like?” or “How did you feel about that?”

The Deeper Truth

Behind all this research is a simple insight about human nature: people want to feel seen.

We spend our days as background characters in other people’s stories. We have thoughts and experiences and dreams that feel significant to us but that no one asks about. When someone shows genuine interest—when they ask real questions and listen to the answers—it’s remarkable how good that feels.

The art of questions isn’t really about technique. It’s about recognizing that the person in front of you has an interior life as rich and complex as your own, and being curious enough to explore it.

That curiosity can’t be faked. But it can be practiced until it becomes natural.

What This Means for You

Quantity matters: People who ask more questions are consistently more liked. If you’re not sure what to do in a conversation, ask another question.
Follow-ups are key: The power is in follow-up questions that show you processed what they said. “What made you decide that?” “How did that feel?” “What happened next?”
Open beats closed: Structure questions to invite elaboration, not one-word answers. “What” and “How” questions work better than “Did you” and “Is it” questions.
Listen to the answers: Questions without real listening are worthless. High-quality attention is what makes questions work.
It’s not an interrogation: Balance questions with self-disclosure. The goal is conversation, not an interview.
Curiosity is attractive: Genuine interest in others predicts better relationship outcomes. The best conversationalists find other people genuinely interesting.

Start your next conversation with one goal: learn something you didn’t know about this person. The rest will follow.

References

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. doi:10.1037/pspi0000097
Yeomans, M., Brooks, A. W., Huang, K., Minson, J. A., & Gino, F. (2019). It helps to ask: The cumulative benefits of asking follow-up questions. Journal of Personality and Social Psychology, 117(6), 1139-1144. doi:10.1037/pspi0000220
Tollison, S. J., Lee, C. M., Neighbors, C., Neil, T. A., Olson, N. D., & Larimer, M. E. (2008). Questions and reflections: The use of motivational interviewing microskills in a peer-led brief alcohol intervention for college students. Behavior Therapy, 39(2), 183-194. PMC5361059
Collins, N. L., & Miller, L. C. (1994). Self-disclosure and liking: A meta-analytic review. Psychological Bulletin, 116(3), 457-475. doi:10.1037/0033-2909.116.3.457
Kashdan, T. B., & Roberts, J. E. (2004). Trait and state curiosity in the genesis of intimacy: Differentiation from related constructs. Journal of Social and Clinical Psychology, 23(6), 792-816. doi:10.1521/jscp.23.6.792.54800
Itzchakov, G., Reis, H. T., & Weinstein, N. (2022). How to foster perceived partner responsiveness: High-quality listening is key. Social and Personality Psychology Compass, 16(1), e12648. doi:10.1111/spc3.12648
Procházkova, L., Míšková, A., & Kret, M. E. (2024). Sharing and receiving eye-contact predicts mate choice after a 5-minute conversation: Evidence from a speed-dating study. Scientific Reports, 14, 5217. doi:10.1038/s41598-024-55772-6