How to talk to strangers when you’re a little shy

You don’t have to be the person who works the room.

I’m actually somewhat shy. I didn’t grow up with much of a network or much emphasis on networking. I’ve had to learn this, and I’m still not the person who walks into a room and instantly knows everybody.

I do love learning from people. If I notice something interesting or have a question I want answered, I have a reason to start talking. That makes the whole thing feel much more natural.

At conferences, I often ask where someone is from. It’s a simple starting point, and the answer can go in all kinds of directions. A city, a move, a community, the reason they came to the event. You only need one place to begin.

I used to see someone I knew on the street and turn the other way so I wouldn’t have to say hi. Seriously. In high school, I watched other kids get opportunities through their parents. Mine opened some doors too, just not in the areas I cared about most. Eventually I realized I could learn to build those relationships myself.

Give yourself a setting that makes conversation easier.

Choose somewhere you would enjoy being even if you only had one conversation. A class, shared activity, or conference session gives you something to talk about immediately.

A recurring activity also gives you another chance to see people. You can say hello today and pick it up next time. That can feel easier than trying to build a relationship during one crowded evening.

When you arrive, notice who seems available for conversation. Someone waiting for the same session may be open to a hello. Someone concentrating, walking away, or occupied with a task may not be. You won’t know exactly what they are thinking, so keep the invitation easy to decline.

• Choose something you are interested in attending.
• Think of one question that fits the setting.
• Give yourself permission to have one short conversation.
• Leave enough attention to notice the answer.

Conversation starters for when you’re feeling shy.

You don’t need an amazing opening line. Honestly, that would put a lot of pressure on the first ten seconds. Notice something around you or ask a question you want answered.

The exchanges below are original fictional examples. Adapt them to what is actually happening around you.

Introduce yourself before or after the opener. If they give their name, use it naturally and continue.

If someone seems occupied, I might start with “Can I bother you for a quick hi?” and a question I’m actually curious about. If they are not engaged, I may make a light joke and leave them to it. I also talk to people next to me on flights when they seem interested. Being nearby creates an opening; it does not mean they owe me a conversation.

I’d skip “What makes you worth meeting?” even as a joke with somebody you’ve just met. It sounds like they’re auditioning. Ask about the event or the thing you’re both doing and give them somewhere easier to start.

Even as a joke, this asks someone to prove their value to you before you have had a conversation. A question about the shared setting gives them something concrete to answer without auditioning for your attention. Use humor you actually share once you know a little more about each other.

“Hey, I’m Sydney. Where are you coming from?”

“What did you think of the part about getting people to share unfinished work?”

“Have you done this before? I’m figuring it out as I go.”

So, what makes you worth meeting? Give me your best pitch.

Follow the part of the answer that interests you.

Suppose someone says they moved to Oakland a couple of years ago. You now have several possible directions: the move, the city, or how they found the event. Choose the one you care about.

Listen for a detail that gives you something to ask. “I moved for work, but I stayed because I found a great music scene” gives you a much more interesting next question than a rehearsed list would.

You can share a little of yourself too. If you only ask questions, they may start to feel interviewed. Give them something they can be curious about in return.

If you know nothing about the topic, you can say that! I think people often enjoy explaining something they care about. “I know almost nothing about this. How did you get into it?” can be a much better conversation than pretending to understand.

“I moved for work, but the music scene is what made me stay.”

“Oh, what kind of music are you into?”

“Mostly small jazz shows.”

“I know almost nothing about that scene. What makes a good place to see it?”

“I came because I’m interested in how people build communities. I work on that too, and I’m always curious about what makes someone want to come back.”

What if they ask what you do?

Sometimes this is the part that feels awkward. Maybe you’re between jobs, figuring out a project, or just don’t think your answer is impressive. You can tell them what you’re learning or what you’ve been spending time on. Give them something real to ask about.

For example, someone between projects might say, “I’m figuring out what I want to build next. Lately I’ve been helping a friend run a small community event.” Someone new to a field might say, “I’m learning enough woodworking to make a table that doesn’t wobble.” Both offer more to talk about than an apology for not having a polished introduction.

Choose a detail you would actually enjoy discussing. If you mention something only because it sounds impressive, the next question can feel like a test. If you mention something you care about, you have somewhere to go. You can also answer briefly and return to what the two of you were talking about. A casual conversation does not require your whole biography.

Let the conversation change shape.

If a person seems engaged despite a short answer, try another easy question. If they keep giving little back, let the conversation end.

When a subject lights someone up, stay with it. Ask how they got into it or what they find difficult. The next question can come from the sentence they just said.

If they mention something personal, slow down. You can acknowledge it without immediately asking for details or offering advice. Let them choose how much they want to share.

They give a brief answer but seem interested in talking.

Try one nearby question: “Have you been to this event before?” Then follow the reply.

They describe a project with enthusiasm.

Ask about one part you genuinely want to understand: “How did you decide to start with that?”

You know very little about their field.

Say so: “I know almost nothing about that. What makes it difficult?”

They keep looking away and give little back.

Leave room: “Nice meeting you. Enjoy the rest of the event!”

They mention a hard experience.

Acknowledge it plainly: “That sounds like a lot.” Give them room to continue or change the subject.

You forgot their name. It happens.

You might forget their name or completely lose your train of thought. It happens. I’d rather acknowledge the awkward moment and keep talking than spend the rest of the conversation trying to hide it.

If you forgot their name, ask again: “Sorry, remind me of your name?” If you lost your train of thought, you can say that and return to something they mentioned. If you have been doing all the talking, hand the space back with a relevant question. You do not need a long apology that makes the other person reassure you.

When you cannot think of anything to say, use the last real detail you heard. They said they recently moved, started a class, or came for a particular speaker. Ask about the part you are actually curious about. You can also let a pause happen. You do not have to fill every second with another question.

Also, don’t read too much into one short answer or a lack of eye contact. People have different styles, and you don’t know what kind of day they’ve had. Give them a chance to keep talking and let them go if they want to leave.

You realize your question was more personal than you intended.

Say “Sorry, you don’t have to get into that,” and offer an easier topic. Let the person decide whether to continue.

You have been talking without leaving much room.

Pause and return to something they mentioned. Ask a real question, then give them time to answer it.

You can move past the usual biography questions.

“What do you do?” can lead somewhere good. “What’s been taking up your attention lately?” also leaves room for a hobby, something they’re learning, or work.

Depth does not have to mean asking for someone’s most vulnerable story. Learning why a person likes a particular activity can be a meaningful conversation. You might discover a way of thinking you have never considered.

If you want to share something more personal, start small and notice the response. A conversation develops through both people offering things, not through one person pushing for a deeper answer.

I once skimmed someone’s LinkedIn before a call and thought we wouldn’t have much to talk about. He turned out to be one of the wisest people I’ve met. One idea stuck: I could help a lot more people by connecting them with somebody who could actually help with their problem. That changed how I thought about building my network. I would have missed it if I’d trusted my first impression.

Joining a group takes a little patience.

I’m still pretty bad at joining big groups. Two, three, or four people is much easier for me. Having a big network hasn’t magically fixed that. If a crowded circle feels hard, try a smaller conversation where you can actually hear each other.

Look for a conversation with physical room to join. Say hello, listen for a moment, and learn what people are talking about before redirecting it. If there is a pause, a simple “Mind if I join you?” is enough.

You can enter through the current topic. “I heard you mention the workshop. How was it?” gives the group a way to include you without starting everything over.

If they seem occupied with a private conversation or don’t make room, move on. Another moment may be easier. You have not failed because one group was not available.

Here is a fictional sequence at a community meetup. Three people are comparing local walking routes. You recognize one route and there is space beside them. The point is to contribute a small piece, then give the conversation back.

If the group carries on without making room, let it. You do not need to compete for a turn. If someone joins while you are talking, a brief recap of the topic can make it easier for them to participate too.

You: Mind if I join you? I caught the part about the reservoir route.

Ari: Sure! We’re trying to find a walk that isn’t packed on weekends.

You: I’ve only been on weekday mornings, so I don’t know the weekend situation. Do you usually go early?

Ari: Usually after lunch. Have you tried the smaller trail behind it?

You: Not yet. What’s that one like?

Ari: Quieter, but a little steeper. I usually bring coffee and take my time.

You: That sounds good. I like a walk with room to stop rather than turning it into a workout. I’m going to grab some water before the next session. Really nice meeting you all!

End while it still feels easy.

A pleasant two-minute conversation can stay that way. Thank them and leave without collecting contact details.

You also do not need an elaborate excuse. If you are heading to a session, say that. If you want to move on, “It was really nice talking with you. Enjoy the rest of the evening” is fine.

When you both want to continue, offer something that fits what you discussed. Sending an article, sharing an event link, or meeting again at the same activity gives you a natural next step.

“Really nice meeting you. I’m going to head into the next session. Hope you enjoy the rest of the conference!”

“I’d love to send you that article we talked about. What’s the easiest place to send it?”

“Are you coming to the next one? It would be fun to hear how your project goes.”

Make the next message belong to the conversation.

If you offered to send something, send it. Mention where you met and the detail that connects the message to your conversation. They may have met several people that evening.

Keep the first follow-up small. Continue the topic without adding several requests.

Then see what they say! Ordinary texts can become a big part of a friendship. I enjoy keeping in touch, especially when we have something we’re both excited to talk about.

After a conversation I want to continue, I ask what the best way to stay in touch is. It might be their number, email, or another channel. I follow up the next day. That gives the other person a chance to place me while the conversation is still fresh, and it gives me a chance to do whatever I said I would do.

Hey Alex, Sydney from the writing event! Here’s the article I mentioned about sharing work before it feels finished. Your point about making the first post less intimidating stayed with me. Hope you enjoy it!

Make the first follow-up easy to recognize.

If you exchange contact details, help the other person remember the conversation. Include your name, where you met, and one specific callback. You can send a promised item or ask about the topic you both enjoyed. Avoid turning the first message into a list of favors, a calendar link, and an invitation to every group you run.

This fictional example continues the walking conversation. The two people agreed to share route ideas. A fitting note is: “Hey Ari, Devon from the meetup! I found the name of that reservoir trail we were talking about. It’s the North Loop. Still curious to try the smaller one you mentioned.” Only use a real route name and share a recommendation you can stand behind in your own message.

If Ari replies with another route, you can ask what they like about it or say when you might try it. If they do not reply, the original conversation still happened. Exchanging a number does not create a promise to keep talking. You can leave the note alone and say hello naturally if you see each other again.

After an event, try recalling one thing you learned from a person rather than counting how many contacts you collected. If you promised something, follow through. If you did not find a natural next step, that is useful information too. You are learning which settings and conversations you enjoy enough to return to.

Do the conference work before the conference.

A lot of the value I get from conferences comes from the pre-work. I look into where people will be, try to get invitations to curated events, and book meetings ahead of time. Having a few real conversations planned makes the event less dependent on whether I happen to walk up to the right person.

I like to dictate notes after each meeting. After a full day of conversations, I remember surprisingly little without them. A useful note captures what we talked about, what the person cares about, and anything I said I would do. It gives the next-day message some substance.

I’ve had days full of brief conversations that led to very little. When I reached out later, people barely remembered me. I’d rather spend enough time with some people that they’re excited to hear from me afterward. Getting everybody’s contact info doesn’t help much if nobody remembers talking to you.

If several people you know are already attending, you can also bring them together yourself. I hosted a casual GDC gathering in Yerba Buena Gardens two years in a row, with over 60 people each time. A lunch with a few people is a much smaller way to try the same idea. Give people a clear reason and place to meet, and let the shared event make the logistics easier.

A shared interest gives you something to contribute.

Chess was an early example for me. I became friends with stronger players, learned from them, and got better. I didn’t have to be the best player to be worth knowing. I could bring enthusiasm, encouragement, and my own perspective. A friendship can have something valuable on both sides even when one person has much more experience.

If you are starting from very little network, choose something you already enjoy and try one-on-one conversations around it. You will have real questions. You may also have a perspective someone else does not: what younger people are interested in, a different community, or an idea from your own work.

When a conversation points naturally toward someone else, you can ask whether there is a person they think you would enjoy meeting. I would not make that a scripted requirement at the end of every call. Let the question fit what you were talking about. The first relationship deserves your attention even if there is no next introduction.

Common questions