How To Make Effortless Small Talk

A guide for the shy, anxious and/or socially inept

Let’s be real: you probably hate small talk.

You hate walking into a room and gritting your teeth through a round of niceties. You never know what to say. You itch to escape the second someone asks how your weekend was.

But you can’t avoid it. Wherever you go, strangers, coworkers, acquaintances, family members, shop assistants and the like seem determined to subject you to inane chit-chat.

Small talk, as excruciating as it can be, serves an important purpose. If you’re shy, it might seem like the worst thing in the world. Yet it’s possible to reframe the way you view small talk and turn it into something positive and fun that soothes, rather than exacerbates, your anxiety.

These days, we’re all so pushed for time that anything that isn’t directly related to ticking items off our to-do lists can seem like little more than a hurdle.

Small talk isn’t, on the face of it, that productive. It doesn’t achieve anything concrete. It’s often the barrier between us and whatever we want to get done. There are few things more annoying than being forced to engage in idle chit-chat when your mind is elsewhere.

But let’s make a distinction between good small talk and bad small talk. If small talk is rammed down your throat by someone who, deliberately or not, ignores all your verbal and non-verbal cues that you don’t want to engage with it, of course it’s going to be unpleasant. It’s basic conversational etiquette to establish as soon as possible if the other person (or people) want to talk to you and to back the fuck off if you get any indication they don’t.

Unwanted mundane conversation isn’t small talk. It’s just someone being a dick.

Small talk matters. It’s conversational foreplay. It should be fun. It’s a light-hearted way of building a connection with someone, learning about them, signalling friendly intent, and adhering to social norms. People who ask heavy-duty questions right off the bat come across as uncomfortably intense and transparent in their attempts to seem deep and intellectual.

Social norms are not evil, they exist for a reason. Think of the last time you had a stranger stand way too close while speaking to you. You probably did everything possible to move away from them. If you didn’t, you spent the whole time wishing you could. That’s because it’s a norm to only stand close to someone you’re intimate with. Skipping small talk is the equivalent of leaning up against a stranger and invading their personal space. You need to maintain a distance before you can even consider getting close. Otherwise, any possible relationship is over before it’s begun.

To give an example, there seems to be a recent trend for people on dating apps to ask if you’d like to ‘skip the small talk and go straight to the first date.’ I am not averse to the spirit of this. Dating apps are for scheduling, not for chatting.

By asking the right questions, I can usually establish within a handful of messages if I want to meet someone or not. If I don’t, I unmatch. If I do, I want something in my calendar within a couple of days, at most, even if it ends up being weeks away. As someone who doesn’t find any intrinsic joy in text-based conversations, for me, the idea is that we schedule a date, at least a few days away, pretty fast — then we do the small talk in the meantime.

If the other person isn’t willing to engage in small talk during the interim period between us scheduling the date and the actual date, I’ll usually cancel. That tells me they view us talking as a means to an end (i.e. getting me to meet them), not as something actually enjoyable. And if they don’t enjoy talking to me, we’re not going to click. That should be obvious.

A lack of interest in small talk with someone translates to a lack of interest in them as a human being.

The same principle applies to any other situation. Small talk is about acclimatizing to each other. If you’re shy, view it as a good thing. The stakes are low, no one is going to freak out if you’re a bit awkward and the potential upsides are open-ended.

Here’s what I’ve learned about the fine art of making small talk as a shy person and some general principles for getting better at it. (Note: this post is based on the notes I’ve made from researching this topic and I am in no way positioning myself as someone who is even particularly proficient at small talk.)


Practice

When we see people who are good at something, it’s easy to assume they’re naturally gifted. If it doesn’t come easy to you, then you must be intrinsically bad at it.

But, as I’ve written before, if something is difficult for you, there is absolutely nothing wrong in coming up with systems and plans for getting better at it. Small talk is a skill.

At the start of 2019, I made a commitment to focusing on getting better with people. Small talk seemed like the right place to start, as it’s something I’ve always struggled with. For instance, in work situations, I’ve a bad habit of walking up to someone or starting a call without engaging in even a few words of small talk first. Eager not to seem inefficient, I’d say hi then jump straight into the intended topic. This is appropriate in some situations and with some people. But all too often, my efforts not to waste their time just translated into rudeness.

People care more about your level of respect for their humanity than they do for their own productivity.

So I read a bunch of books on the topic (and thank you to several readers who sent me books about small talk.) I researched it. I paid attention to the way other people engaged in chit-chat. I eavesdropped. I made an effort to add a sentence or two to mundane exchanges.

As the nuclear option for improving my social skills, I moved into a quasi-commune-ish situation with 25 other people (plus myriad visitors, partners, and random tag-alongs) in one house. I figured I’d stay for a couple of months, use it as a sort of exposure therapy. After nearly three months, it’s had a profound positive effect on me. I have to meet new people almost every day so I’m constantly practising small talk.

These days, I also make an effort to go out and meet people whenever I have time. It’s still hard work much of the time, most weeks I can’t manage anything social, and some/most days I don’t want to engage with any of my housemates so I hide away. In general though, the total lack of privacy has been an effective forcing function.

The point here is: take every possible opportunity to practice. You are probably not so socially inept that you need to take the kind of drastic action I did. But I tell my own story because it shows that there is no shame in making a focused effort to practice your social skills if you know they’re abysmal.

Low stakes, casual situations with people you’re unlikely to see again are ideal. Turn it into a game, if that helps. Go to events where you can practice. Indulge chatty housemates or family members. It might not always be riveting, but it will flex the small talk muscle. You’ll build up an intuitive grasp of the nuances and patterns that work.

I’ve seen suggestions to strike up a conversation with baristas, shop assistants and the like, but this seems like a bad idea unless they’re not otherwise occupied and give strong signals that they’re happy to chat. It’s one thing to ask a few casual questions while someone is ringing up an order or whatever. It’s another to corner them for your own benefit, while a queue piles up behind.

The point is, small talk is a skill. Like all skills, you can improve it through practice.


Ask questions

The foundation of small talk is asking questions. It’s a cliche that being interested makes you seem interesting, but it’s true.

People like people who help them momentarily forget the universe’s dreadful indifference to their existence.

So get asking. Get comfortable with being the one to lead the small talk. Ask open-ended questions that can’t merely be answered with a yes/no. Follow up on the detail. Be as sincere as possible. Make eye contact and lean forward a little to show genuine interest. When perfunctory exchanges are the norm, it takes extra effort to indicate to someone that you want to hear what they have to say. If you’re only getting one word answers, say something that shows your interest is real. And don’t look at your phone unless you need to.

It doesn’t matter if you’re truly interested in the minutiae of their day job or the intricacies of their coffee order. Once again, the point of small talk is not entirely the content of the conversation. It’s about keeping it flowing — as a social nicety, as a precursor to more serious conversation, or to establish a relationship.

If it helps, preprepare generic starting questions for situations where you’re likely to need to engage in small talk. The hardest part is often getting started, yet it only takes a couple of initial questions to get the momentum going. Before you walk into the room at an event or turn to the person next to you in a queue, think up a couple of things to remark upon. Much like making a deliberate effort to practice small talk, there is nothing artificial about doing this.

I did once go on a date with someone who admitted they scripted out entire conversations for dates. That’s a bit too far. It was like talking to a bot. Preplanned questions are a starting point. Scripting whole conversations means you’re not focused on the other person’s actual responses. Once the small talk gets started, respond to the last thing the other person said. Otherwise, it will feel like an interrogation and has a good chance of getting their guard up. The purpose is to relax everyone involved, not to collect information.

Leave a beat once someone finishes talking before firing off other questions, but be prepared to fill gaps. Don’t get too personal in what you ask. Small talk is not the time for it, even with someone you already know. With strangers, I prefer to preface anything that could be construed as intrusive (e.g. asking which area of London they live in or what they do for a living) with ‘if you don’t mind me asking’ or something similar.

There seems to be a vogue for asking off-beat, unusual questions. It’s a fine line. Per one suggestion, I tried asking people at a party “So, how do you like to suffer?’ As you might expect, the answers were, for the most part, befuddled and not particularly revealing. That said, deviating from the standard questions in a sensitive way can be revealing. “How do you spend most of your time?” or “What are you passionate about?” almost always go down better than “What do you do?”, especially if they dislike their job or don’t consider it interesting. Not everyone identifies themselves by their job title. Some of us, myself included, don’t have a defined job title to spit out either.

There’s a time and a place for “So, which parent were you closer to?” Small talk is not it.

Overly vague questions (like “Tell me about yourself” or “What are you about?”, both of which I’ve heard of late) are not a good idea. They put too much pressure on the other person to figure out what to respond with. Open-ended questions are best followed by more specific ones.

Unless you’re stuck with a full-blown conversational narcissist, most people will switch the focus over to you after you’ve asked a few questions. Don’t give a monosyllabic response then revert to asking questions or the situation will get uncomfortable. Give enough detail to allow them to ask questions in return. Your responses don’t need to be long-winded, but a complete absence of detail will make the exchange feel unbalanced. While we’re at it, try not to be the conversational narcissist in the room. As easy a mistake as it is to make, doing nothing except talk about yourself without asking questions is not fun for anyone else.

The nice side to asking questions is that it gives you breathing room to get your bearings and settle into the conversation a little more. Small talk is less nerve-wracking if it’s not about you.


Establish points of connection

There’s a part early on in Scoop, a satirical novel about journalism by Evelyn Waugh, where two of the characters bond over the realisation that neither of them likes tinned salmon. As comical as that sounds, a big component of small talk is finding things you have in common with each other.

Look for points of connection. In an age of increasing loneliness and disconnection, it’s hard to overstate the value of a face-to-face conversation with someone whose world intersects with yours, even a little.

Certain topics are an easy fallback. Train lines. Outrageous city prices. Kids. Pets. The weather. Shocking new events. Locations you’re both familiar with. Any overlap in hobbies or jobs. Food or drink preferences. If you spot a point of connection, pounce on it and let them know. I read a lot, and widely, which helps as I can often ask people if they’ve read a book relevant to something they mention.

Carol Fleming writes in The Serious Business of Small Talk that:

‘To me, small talk is the sound of people reaching out to each other. It’s the sound of people looking for ways to find similarities, shared interests, goodwill and the offering of friendship, not for any particular instrumental purpose, but because we need eaxh other. We hunger for human contact. Small talk is a linguistic mechanism that allows Us (you and me) to transform Them (a stranger, a scary other) into someone who is part of our tribe, into an Us.’

Observe

Perhaps the most important aspect of small talk is remaining focused on the other person and their signals.

As I mentioned earlier in this post, most of us hate small talk because we’ve been exposed to so much of the bad sort; when someone doesn’t pay to verbal or non-verbal cues that you’re not interested in talking to them.

So don’t be that person. Never force small talk on anyone who doesn’t seem receptive, in particular if you’re in a situation where it could come across as threatening or demanding (e.g. if they have headphones in or on public transport.) Don’t take it personally either. It feels wrong to even have to say this and the kind of people who attempt to force small talk are not likely to care about how it affects others, so I won’t say anymore. Likewise, if someone seems reluctant to discuss a particular topic, don’t push it.

Otherwise, observe how people respond to your questions to know what else to ask. Not only does the content of responses contain clues, so does the way it’s delivered.

Melissa Wadsworth, writing in How To Make Small Talk: Conversation Starters, Exercises, and Scenarios points out that in any small talk situation there are certain factors that are out of your control:

  • The other person’s personality
  • What they have on their mind
  • Their schedule
  • The number of competing demands on their attention
  • And the presence of cliques.

The only thing you can control is how you act and interact. You have to work with the raw material given to you.


Keep it positive and avoid assumptions

On one occasion when I was 19, I was at a networking-type thing, making small talk with a group of people. One of them shared the concept behind the app they were working on. It was something of vague interest.

That sounds fascinating I said,” then added with the teenage snark I hadn’t yet started making an effort to divest myself of, “I’m so sick of hearing that people are making a social network for musicians.”

There was an uncomfortable pause before someone in the group stated she was in the process of making a social network for musicians. I made a hasty retreat. And that’s a cautionary tale in the importance of keeping small talk light-hearted and not making assumptions about conversational partners.

As Melissa Wadsworth writes:

‘You never know who’s responsible for particular aspects of the event (the food you just criticised ight have been catered by the man you’re speaking with) or who knows whom. Judgements and putdowns are bad conversation crutches and not many people are thrilled to engage in negativity for long. You want to generate an upbeat aura, not chalk up bad social karma.’

While there are situations where small talk blooms over mutual complainings and it’s appropriate, it’s best to avoid anything that could backfire and offend someone. British people talk about the weather so often because it’s a neutral topic. Everyone agrees that rain is bad and sun is good.

As The School of Life puts it;

‘Small talk exists for a noble reason: it is designed to prevent hurt. It provides us with a rich source of information so that we can safely ascertain the frame of mind of our interlocutor — and therefore gauge what more in-depth topics of conversation might safely be broached.’

Likewise, small talk should be light. Oversharing or revealing too much personal information in a manner that asks a stranger to perform emotional labour for you is a violation of basic boundaries.

You never know what frame of mind someone will be when you start talking, so it’s best to treat with care until you’ve gauged their mood. Small talk with people you do know, like coworkers before a meeting, has equal value for this purpose. It lets people supply some context for their current state and lets us assess how best to treat them.


Move to big talk when/if it’s appropriate

There’s a verse from Sugar Street by Conor Oberst that exemplifies the way small talk leads into big talk:

‘If you start at the beginning and go on to the end
Sometimes a perfect stranger might end up your only friend
First you nod politely because you’re not that interested
Ask some abstract question like a bored psychiatrist
But then you get to talking about the plastic in the sea
The nightmare of their childhood and reality TV
It starts to sound familiar like you’re coming back to life
Make some observations, start offering advice.’

In many cases, small talk is an end in itself. Sometimes though, it’s the start of a deeper conversation and more meaningful relationship. There comes a point where small talk is no longer enough and it’s right to start discussing childhood traumas and environmental disasters and the decline of popular culture.

Small talk serves as the precursor to big talk. With people you already know, it’s a chance to settle into the conversation and indulge in trivialities. With strangers or those you barely know, it establishes that you’re sane and worth trusting. Some relationships never go beyond small talk. Sometimes hitting the deep topic feels appropriate early on, as when you just click with someone. Sometimes it takes months or years of chit-chat to build up to anything more.

There’s only way to find out what a relationship can be: smart small.


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