Good Questions to Ask People (Fun, Random and Interesting)

The best questions to ask are the ones people don’t get asked every day: about their choices, their stories and what they’re into right now, not their job title or the weather.

30 good questions to ask, from light to interesting

Someone you just met 5
Coworkers and bosses 4
Family 3
Friends, fun and random 8
Interesting questions and follow-ups 8
Open vs. closed questions 2

It's a family birthday at your aunt's house. After cake, most of the younger relatives are on their phones. Your grandma Bea is sitting in the armchair by herself. You visit a few times a year, and you realize every conversation you've had with her lately has been about her knee.

Grandma Bea

sits with her hands folded, watching the room with a small smile, looking up when you pull a chair over

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30 good questions to ask, from light to interesting

These questions to ask are grouped from easy openers to the fun, random and more interesting ones. Each row shows when to ask it and the weaker version to skip in the same moment.

Someone you just met

Someone you just met at an event“How do you know everyone here?”Skip: “So what do you do?” as the first question
They mention they’re new in town“What made you pick this city?”Skip: “Do you like it here?” (gets a polite “yeah”)
They tell you what they do for work“How did you end up doing that?”Skip: “Oh, cool.” (and on to the next topic)
They call their own job boring“Nope, you don’t get off that easy. What’s the part nobody knows about?”Skip: “Ha, yeah, sounds pretty dull.”
They mention a hobby“What got you into that?”Skip: “Isn’t that expensive?”

Coworkers and bosses

A Friday conversation with a coworker“Anything you’re looking forward to this weekend?”Skip: “Any big plans?” (sounds like pressure to have some)
Monday, same coworker“What was the best part of your weekend?”Skip: “How was your weekend?” (gets “good, yours?”)
Your first one-on-one with a new boss“What do people usually figure out about working with you around month three?”Skip: “So, what do you expect from me?”
A colleague who’s been there for years“What do you wish someone had told you in your first month here?”Skip: “Is it true this place is a mess?”

Family

A grandparent or older relative“What’s the most trouble you ever got into when you were my age?”Skip: “How’s your health?” (again)
A parent, on a quiet evening“What were you like at my age? What did you worry about?”Skip: “Why did you do things that way?” (sounds like a verdict)
A kid or teenager in your family“What’s something you’re weirdly good at that adults don’t know about?”Skip: “How’s school?”

Friends, fun and random

A friend back from a trip“What surprised you most about it?”Skip: “Was it fun?”
A friend who just finished a big project“What are you proudest of in how it turned out?”Skip: “So what’s next?” (before they’ve even exhaled)
Fun question for a group dinner“What’s the worst job you’ve ever had?”Skip: “How much do you all make?”
Fun question with friends“What’s a hill you’ll die on that nobody else cares about?”Skip: “Who here do you like least?”
Random question, late night“What’s a smell that instantly takes you back somewhere?”Skip: “So… what now?”
Random question on a long drive“If you had to teach a class on something, what would it be?”Skip: Asking “what are you thinking about?” every ten minutes
Funny question when things are relaxed“What’s the most useless skill you have?”Skip: A question that makes one person the joke
Weird question for a friend who likes weird“What’s a food combination you love that other people think is gross?”Skip: “Would you rather…” games that go gross fast

Interesting questions and follow-ups

Interesting question once you’re comfortable“What’s something you’ve changed your mind about recently?”Skip: “What are your politics?”
Interesting question about their past“What did you want to be when you were ten?”Skip: “Do you regret not doing that?”
When they seem excited about something“Okay, what’s the best part about it for you?”Skip: “Hm. Doesn’t that get old?”
When they seem tired or stressed“What’s been the hardest part of this week?”Skip: “Are you okay?” (gets “yeah, fine”)
After they tell you a story“Wait, what happened after that?”Skip: “That reminds me of the time I…”
When they recommend something“What do you love about it?”Skip: “I’ll probably never get to it, honestly.”
Someone who knows a lot about a topic“What’s the most common thing people get wrong about it?”Skip: Correcting them with something you read once
Wrapping up a good conversation“What’s the one thing you’d tell me to try, since I’m new to this?”Skip: Just trailing off with “anyway…”

Open vs. closed questions

Closed question (fine for plans)“Are you free Saturday at noon?”Skip: “We should hang out sometime.” (no real question at all)
Open question (better for stories)“How did the interview go? Tell me everything.”Skip: “Did the interview go well?”

Open vs. closed questions to ask

A closed-ended question can be answered with yes, no or one word: “Did you like it?”, “Are you from here?”, “Is it far?” Closed questions are great for plans and quick facts. An open-ended question asks for a story or a reason: “What did you like about it?”, “What brought you here?” When you’re trying to get someone talking, most of your questions to ask should be open. Opening questions can be simple, as long as they leave room for more than a one-word answer.

How to ask good questions in conversation

Good questions to ask people only work when they fit the moment and you do something with the answer. Here’s how to ask them so they open people up.

1 of 4

Match the question to the moment

In a checkout line, ask about the thing in front of you — the easiest way to start a conversation. At a quiet dinner with friends, ask the weird ones. With a new boss, ask how they like to work. The same questions to ask can feel warm or strange depending on where you are.

A stranger at the dog park

Sorry, he’s friendly. Just nosy.

Flat reply

“No worries! So what do you do for work?”

“Uh, I’m a nurse.” They call the dog back over.

Better reply

“Ha, no worries. How old is he? He has so much energy.”

“Two, and he never runs out.” They stay while the dogs play.

Why it works: At the dog park, ask about the dog. Let the moment pick the question.

2 of 4

Ask about choices, not just facts

“Where are you from?” gets a place name. “What made you move here?” gets a story. When you pick questions to ask someone, reach for the “why” and “how” behind the fact, and keep the tone curious, not like a cross-examination.

A friend of a friend at a barbecue

I used to be a lawyer, actually. Now I teach middle school.

Flat reply

“Oh, nice. What grade?”

“Seventh.” A nod, and the conversation idles.

Better reply

“Okay, that’s a big switch. What made you make the jump?”

They laugh: “Short version? I hated billing hours.” Then the long version.

Why it works: Asking what made them switch gets a story. “What grade” just gets a number.

3 of 4

Answer it yourself too

Good questions to ask people, especially questions to get to know someone, work best as a trade. Ask, listen, then offer your own answer. It keeps things even, and it shows the other person how deep you’re willing to go.

A coworker at lunch

Last thing I binged? Honestly, a show about people restoring old boats.

Flat reply

“Ha, nice. What else are you watching?”

They name two more shows, then wait for your next question.

Better reply

“I love that. Mine was a baking show. I watched all six seasons in two weeks.”

They laugh: “No judgment. Which one?”

Why it works: Answering your own question makes it a trade instead of an interview.

4 of 4

Follow up on what they actually say

The first question only opens the door. The follow-up (“wait, how did that happen?”) is what makes people feel listened to. If you have a list of questions to ask, use it only when the conversation stalls, not as a script.

Your roommate, getting home late

Sorry, I’m late. I got stuck helping some lady change a tire on the highway.

Flat reply

“Oh wow. Did you see the landlord’s email?”

“Not yet.” The tire story never comes up again.

Better reply

“Wait, on the highway? How did you end up doing that?”

“So she’s on the shoulder waving her arms…” They drop their bag and sit down.

Why it works: Following up on what they actually said is what makes them feel listened to.

Questions to ask carefully (or not at all)

Running down a list. Five questions to ask in a row with nothing of yours in between feels like an interview.
Asking deep or juicy questions too early. “What’s your biggest regret?” needs trust first.
Closed questions when you want a story. “Did you like it?” gets “yeah.” “What was the best part?” gets more.
Asking and then looking at your phone while they answer.

Questions to ask: FAQ

What are good questions to ask people?

Good questions to ask people are easy to answer and point at something they care about: “How did you end up doing that?”, “What are you looking forward to this week?”, “What’s something you’ve changed your mind about?” Questions about choices and stories beat questions about facts.

What are fun questions to ask?

Fun questions to ask with friends or a relaxed group: “What’s the worst job you’ve ever had?”, “What’s a hill you’ll die on that nobody else cares about?”, “What’s the most useless skill you have?” Go first with your own answer so it feels like a game, not a test.

What are some random questions to ask someone?

Random questions to ask someone work best late at night, on a long drive, or with people you already know: “What’s a smell that takes you straight back somewhere?”, “If you had to teach a class on something, what would it be?” With a stranger, stick to questions about the moment you’re in.

What are good questions to ask to start a conversation?

The best questions to ask to start a conversation are about the shared setting: “How do you know the host?”, “Have you been here before?”, “Is this line always this long?” They’re easy, low-pressure, and they give you something to follow.

What is an example of a closed-ended question?

A closed-ended question can be answered in a word: “Are you from here?”, “Did you like the movie?”, “Is it far?” To open it up, ask for the story instead: “What brought you here?”, “What did you think of the ending?”

How do you ask good questions in conversation?

Ask one question at a time, match it to the moment, and follow up on the answer instead of moving to your next question. The follow-up is where people feel heard. It also helps to answer your own questions to ask, so the conversation stays a trade.

Meet Communicate Better

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Communicate Better is built for one thing: helping you communicate better. Step into real moments, say it your way, and see how it lands — until the right words come without thinking.

Learn more about Communicate Better →

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