How to Make Small Talk: A Practical Guide for Teenagers and Young Adults

If you have ever wanted to actually know somebody rather than just exchange facts with them, the questions on this page are the ones that get you there. They are sorted by how well you know the person and how much they have warmed up, because asking the right question at the wrong moment is most of what makes a conversation feel like an interview.

I have coached this for more than a decade. The single most common mistake I see is not asking bad questions. It is asking a good question far too early, getting a short answer, and concluding that the other person is not interested.

The first five minutes

These are for somebody you have just met. They are ordinary on purpose. Their job is to get the person talking and to give you material, not to be memorable.

• "What do you do most days?"
• "How did you end up doing that?"
• "Have you always lived around here?"
• "How do you know everyone here?"
• "What are you working on at the moment?"
• "What did you do before this?"
• "What do you do when you are not working?"

If I could keep only one question from this entire page it would be "how did you end up doing that?" Almost everybody has a story about how they got where they are. Most people enjoy telling it, most people are rarely asked, and the answer usually hands you three or four new things you could ask about next.

Once it is going

Use these after a few minutes, when the polite opening is over and neither of you is scanning the room. They are still safe, but they ask for an opinion or a preference rather than a fact, which is where a conversation starts to feel like a real one.

• "What have you been into lately?"
• "What is something you are weirdly good at?"
• "What is taking up most of your time right now?"
• "What is the best thing that has happened to you this month?"
• "What did you want to be when you were a kid?"
• "What is something you could talk about for an hour?"
• "Are you more of a planner or do you wing it?"
• "What would you do all day if nobody was paying you?"

Notice how specific these are. "What are your hobbies?" gets you a list. "What is something you could talk about for an hour?" gets you the thing they actually care about, which is a completely different conversation.

Questions that get real answers

These are for somebody you have been talking to for a while, or somebody you already know a little. They ask the person to think, and a short pause after one of them is a good sign rather than a bad one.

• "What is something most people get wrong about you?"
• "What is something you have changed your mind about?"
• "What are you avoiding right now?"
• "When were you happiest?"
• "What do you wish you had started earlier?"
• "Is this what you thought you would be doing?"
• "What is the last thing you got genuinely excited about?"
• "What is something you are proud of that nobody knows about?"

Keep in mind that these only work once somebody trusts that you are actually interested. Ask one of these in the first two minutes and it lands as strange. Ask it twenty minutes in, after you have listened properly to three smaller answers, and people will tell you things they have not said out loud in months.

Lighter questions, for a group or a long drive

Sometimes you want the temperature to go down rather than up. These are useful in a group, in a car, or when a conversation has gone flat and needs restarting.

• "What is the most useless skill you have?"
• "What food would you eat every day if it had no consequences?"
• "What is the worst haircut you have ever had?"
• "What is a hill you would die on that nobody agrees with you about?"
• "What was your first job like?"
• "What is something you are irrationally afraid of?"
• "If you had to give a talk tomorrow with no preparation, what would it be about?"

Questions for somebody you already know

This is the version people ask me about most, and it is a different problem. You already have the basic facts, so the ordinary questions feel repetitive and the conversation settles into "how are you, fine, you?"

• "What is going on with [the thing they mentioned last time]?"
• "What has been the best part of your week?"
• "Is there anything you are dreading right now?"
• "What are you looking forward to?"
• "What is something you have been meaning to do and keep not doing?"
• "Who have you been spending time with?"
• "Has anything surprised you lately?"

The first one is the most useful thing on this whole page and the one people skip. If somebody told you last week that they had a job interview, or their mother was in hospital, or they were nervous about a test, asking about it now takes eight seconds and tells them you were listening. Almost nobody does it.

What to do with the answer

Now the part that matters more than any question on this page. If you ask a good question and then move straight to the next one, you have run an interview, and the other person will feel it even if they cannot name it.

The first move after they answer is to respond to what they said. If you ask what they have been into lately and they say "mostly running, weirdly," don't reach for your next question. Say something about it. "Weirdly? Did you not expect to like it?" That single follow-up does more for the conversation than the original question did.

The second move is to give something back without being asked. Most people answer and then wait, which quietly puts all the work on you. Volunteering a small piece of yourself takes the pressure off them. "I tried running in January and lasted about nine days." Two sentences, and you have handed them several things they could ask you about.

And go one question deeper than feels natural. First answers are polite and shallow, because the person has not decided yet whether you actually want the real answer. The second or third question on the same thread is usually where the real one appears.

A few honest caveats

Some of these will not sound like you, and a question that does not fit your own mouth is worse than a boring one that does. The questions near the top of this page work perfectly well and they work for everybody.

Don't work down the list in order. Three questions in a row with no reaction from you is exactly what makes somebody feel processed. One question you genuinely follow up on is worth more than six you fire off.

And some people will give you short answers no matter what you ask, and that usually has nothing to do with you. They are tired, or late, or having a bad week. If somebody answers in three words twice in a row, that is information, and the right response is to let them off rather than dig harder.

Where to start this week

Pick two questions from the first two sections. Use them on somebody ordinary, in an ordinary situation, and pay attention to what you do after they answer rather than to how you delivered the question.

Then do it again in a few days. The reason this gets easier is not that you memorize better questions. It is that you slowly stop worrying about what to ask next, because you learn that the other person hands you the next thing if you are listening for it.

If the part that trips you up is the opening rather than the middle, conversation starters that actually work covers the first ten seconds. If you want subjects rather than questions, conversation topics and questions to ask is the companion to this one.