Short of time? Here are the key takeaways:

**❓ People differ widely in how much they enjoy chatting with strangers. **Some actively welcome it, while others strongly dislike it. Because you can’t reliably tell in advance, good conversations start with sensitivity to signals of interest or disinterest.

**🌱 Conversations get easier when you steer toward what the other person cares about. **Asking what they’re genuinely interested in, and then following up thoughtfully, often leads to faster, more engaging discussions than relying on surface-level small talk.

**🔍 Good conversations are built through attentive curiosity, not cleverness. **Asking open follow-up questions, listening carefully, and looking for what makes the other person interesting or animated helps conversations feel meaningful rather than awkward or interview-like.

🧠 Many people worry more than necessary about how they come across. Research suggests we underestimate how much others like us, how interested they are in deeper conversation, and how open many people are to connecting with strangers.

Jonathan Dunne didn’t enjoy his commute through London for his job. For one thing, the people on the underground ‘Tube’ transport system didn’t talk to each other. So he attempted to start a movement to combat that. He handed out badges emblazoned with the phrase ‘Tube chat?’, hoping that people who wanted to break the silence and enjoy a chat with a stranger would be able to see the badges and strike up conversations without fear of rejection or reprisal.

The movement gained attention very quickly and received near-immediate backlash. Within two days, a counter-movement called ‘Shut up!’ was handing out badges so that people could signal to their fellow passengers that they’d “rather drink a pint of bleach than talk with them!” And Dunne reported that, initially, “it was an 80-20 split between people hating the idea and liking it.” (Eventually, he said, it settled down to around 50-50.)

The story illustrates something you probably know well: some people seem to love talking with strangers or acquaintances, while other people dread it.

For better or worse, we can’t always wear a ‘Shut up!’ badge and avoid conversations with strangers or acquaintances. Many people regularly encounter contexts in which conversing with strangers is necessary. Whether that’s at a new job, when dating, making new friends, after moving to a new part of town, or any number of other situations. So, it can be very helpful to have some strategies up your sleeve that can make such conversations go more smoothly. That’s where this article comes in.

In what follows, we’re going to give you 7 very simple (but we believe, quite useful) strategies for making conversations with strangers or acquaintances be interesting, go more smoothly, and be punctuated by fewer awkward silences.

Given the evidence that conversations with strangers and acquaintances might contribute meaningfully to happiness (some of which we’ve talked about before), these strategies may be valuable for anyone who wants a little help navigating their nuances. We expect that some will seem obvious, but we think they can all be helpful.

Strategies for easier conversations with strangers

First, an important caveat: Some people really don’t want to be spoken to. You might have the best intentions when you’re attempting to start a conversation, but there is always a chance the person you’re talking to simply won’t be interested (particularly if they don’t know you). Unfortunately, people aren’t typically wearing badges that indicate their willingness to talk (despite Jonathan Dunne’s attempts), so you’ll have to pay attention to their demeanor and what they’re saying. If they indicate that they aren’t interested, respect that!

Let’s assume you’ve found a conversation partner who is willing to chat. You don’t know them very well (perhaps you’ve just met) so what can you do to improve your odds of having a good conversation? Here are seven strategies. Although they can each be used at any time during a conversation, we’ve organized them roughly by when you’re most likely to employ them. If you think you’re someone who struggles with getting conversations started, you might be most interested in the first two. If you struggle with getting past lulls or how to keep things moving, you might be interested in the later suggestions.

Starting Conversations

1️⃣ Find Interest Around You

If there’s something interesting in the environment, remark on it and ask what their reaction to it is, or open the door for them to comment on it too. For example:

“I just noticed that the house has a different style of architecture from the others. Do you like its style better or worse?”

This can be an especially easy way to start a conversation with a stranger - by asking about something in the current environment, or remarking on something you both experienced (e.g., you’ve both just watched the same performance).

A slightly higher-risk version of this involves asking your conversation partner to speculate. For example:

“I just noticed that the house has a different style of architecture from the others. Why do you think that is?”

Some people won’t appreciate being asked to hypothesize on the fly, or will simply reply that they don’t know (which can feel like an ending to the conversation) - but some curious people will have their interest piqued and will join you in crafting theories, which can be a gateway to more interesting conversation.

Note: As conversation progresses, this strategy can come with more risk because, if you’re too obviously looking around for things to talk about, others might interpret you as uninterested or awkward.

2️⃣ Ask what sort of things they are interested in

This can be a slightly awkward question, but we think it’s often worth it. In our experience, it tends to have a good payoff in that it helps you jump to talking about something the other person cares about. Sometimes people will talk about work (when they enjoy it), but other times, they will bring up an idea they are interested in or a hobby they are passionate about, etc. From there, we find it’s typically much faster to get to mutually interesting conversations than if we started with small talk.

For instance, to get past small talk with someone he’s just met, Spencer likes to ask, "What topics or things are you really interested in?" Usually, the person will list two or three things, and Spencer will then ask a follow-up question about one of them, knowing already that this is a topic that interests the other person (so they’re more likely to enjoy discussing it).

Keeping Conversation Going

3️⃣ Ask follow-up questions

This is probably obvious, but it’s worth saying. Open follow-up questions are one of the easiest ways to keep a conversation moving. Of course, the principal difficulty with them is coming up with the questions themselves. Fortunately, there are a range of questions that are widely applicable across a great many topics. For instance, if you end up talking about their work, a hobby of theirs, an event they’ve been to, or things along those lines, you can try asking open questions like:

What do you most like about it?

What do you find most challenging about it?

What drew you to it?

What’s harder about it than people usually expect?

What do you think people usually get wrong about it?

What part of it feels most ‘you’?

If delivered sincerely, questions like these can signal interest in a person - and since they’re open questions (not just requiring a “Yes” or “No” response), they give the person you’re talking to a chance to talk about things that matter to them. But, beware! Merely asking questions is not the same as attentively listening to the answers, and too many questions might make the conversation feel one-sided or like an interview. Try to keep the balance of your speaking in the 40% to 60% range - most people prefer it that way.

4️⃣ Find their Interesting Details

Start by assuming the other person is worth knowing and giving them the benefit of the doubt. Then set yourself a challenge: Now, your job in the conversation is to explore what’s interesting about this person. See whether you can leave the conversation able to fill in the blanks in this statement:

“I thought ____ was so interesting because _____”

This approach has the added benefit that most people enjoy others being interested in them and paying close attention when they speak - so unless the other person finds you off-putting for other reasons, taking this approach is more likely to leave your conversation partner feeling good.

5️⃣ Find Out What Makes Them Light Up

Similar to the above, this one involves assigning yourself a challenge. In this case, it’s the challenge of figuring out what they most enjoy talking about. Here’s the catch: You’ve got to do so without directly asking them. Asking “What would you most like to talk about?” puts uncomfortable pressure on them, so ask questions about their thoughts and interests to discover the topic that makes them light up the most.

Getting Past Lulls in Conversation

6️⃣ Raise Something You’ve Been Pondering

If the conversation lulls, you can try saying something along the lines of, “This is random, but I’ve been thinking a lot about something lately, and I’m curious what your take on it would be. Do you mind if I get your take on it?” Then, if they consent, ask a question you’ve been pondering (e.g., “How do you decide how much time to spend making new friends?”)

From personal experience, being on the receiving end of this can be delightful. It can be a clear signal that the person talking to you has an interest in talking more, that they want to dig into a topic that interests them with you, and that they value your input.

The preamble (about it being random and asking if it’s okay to get their take) might seem superfluous, but it makes it much less awkward. If you just blurt out an unexpected question, “How do you decide how much time to spend making new friends?” to someone who doesn’t already know you well, then it may come across as jarring or odd (in a bad way). But acknowledging the randomness of it softens it.

Benefits of this kind of question include:

It’s an easy way to move past superficial small talk

You can tailor it to a topic you know you’re interested in

It’s the sort of thing you can prepare before a social occasion

7️⃣ Offer a Sincere Compliment

Pay close attention to the other person’s vibe and make a positive (and genuine) observation about their personality or manner (not their body!). For instance, if they have a really pleasant-sounding voice, tell them that. If they give off a lot of confidence, compliment them on it.

If giving compliments is something you’re nervous about or lack confidence with, you could try our *Compliment Without Awkwardness *tool (it’s free):

None of these strategies relies on being naturally witty or extroverted. Instead, they aim to steer the conversation towards topics that you and your conversation partner will both find interesting. Whether that’s by **trying to understand what interests them **(2–5), or contributing something you find interesting in a way that invites them to engage, in a low-pressure way (1, 6–7). If you want to put these strategies into practice, we suggest picking one or two that resonate most with you and feel achievable, then making a deliberate, conscious effort to try them the next time you’re in conversation with a stranger.

Good news for unconfident conversationalists

We hope that the above will help you to engage in conversations more confidently and comfortably. But, if you’re still worried, some good news can be found in empirical research. For example, findings suggest that:

After talking with strangers, people systematically underestimate how much their conversation partners like them. (More evidence here and here.)

People tend to overestimate how awkward their conversation partners find ‘deep’ conversations and underestimate how much others care about their ‘deep’ disclosures.

People tend to underestimate how interested other people are in connecting with strangers. (Though, of course, some people genuinely do not want to be talked to, and you should respect that if they tell you as much.)

This is all evidence that, if you are worried about how well you converse with strangers, you’re probably more worried than is warranted! Nevertheless, we hope our 7 simple tips above can reduce your worry even more.

Of course, it’s possible the other person just doesn’t want to engage with you. It’s important to stay attuned to how the other person is feeling and not push them beyond the level of engagement that they feel comfortable with.

But when done skillfully, strategies like these often make the conversation much more interesting for everyone involved.