Conversations Don’t Need To Be a Conspiracy of Politeness

How to recognize and use the liking gap to your advantage.

Sean Kernan
6 min readJun 11, 2024
Pexels images via Nappy

It’s fascinating when I see social anxiety on full display.

Some people will light up and start laughing at everything you say, power-smiling and telling jokes constantly, seeming remarkably cheerful at your presence.

I know they aren’t like this when alone in their house. Such exuberance would border on madness if continued in perpetuity. In one interaction, a guy got excited and spent 15 minutes telling me about a comedy show he went to. Perhaps he was just excited about the comedy show. But I felt tons of nervous energy emanating from him.

Such interactions speak to our common fears of judgement and likability. But they are disingenuous— and many people don’t realize it.

We aren’t typically malicious in small talk

The odd thing is that, despite hating it, so many of us fall into the trap of small talk, and asking where the other person is from, where they went to school, what they do for fun, and what their favorite movie is. These are all noble and well intended questions. But they are often driven by social anxiety — which is far from a new problem.

One of the first descriptions of it came in 1621, in Robert Burton’s The Anatomy of Melancholy, referring to one of Hippocrates's patients, “He dare not come into company for fear he should be misused, disgraced, overshoot himself in gestures or speeches, or be sick; he thinks every man observeth him.”

In Sara Wheeler’s biography Terra Incognita, she revealed that William Wilson, the doctor on the ill-fated trip to the south pole struggled immensely with socializing, saying, “Yet back at home he found normal social intercourse so difficult that he confided to his diary that he took sedatives before going to parties, and one of his biographers wrote that it required far more courage for him to face an audience than to cross a crevasse.”

Our desire for acceptance and group belonging is rooted in survival. Ostracism from the group was correlated to many negative health and life outcomes. One review of the academic literature states, “Existing evidence supports the hypothesis that the need to belong is a powerful, fundamental, and extremely pervasive motivation.”

This is why I, perhaps like you, will often be driving home from an event and reliving some off comment I made, wondering if it made a bad impression, or hoping it didn’t come across in a bad way. I hate that this happens. But it goes both ways.

During one talk with a woman, we were discussing our careers, and she blurted out her exact salary she was making (which was substantial). It caught me a little off guard as I’d never had a stranger tell me such a figure. I suspect she might have been slightly uncomfortable after having said that — and perhaps regretted it later. For the record, it didn’t bother me either way, as I could tell she wasn’t doing it to lord over me or assert herself as more important.

Rethinking these interactions

These odd behaviors we exhibit and diving to get people’s approval really isn’t necessary. Dr. Erica Boothby, of Cornell University, ran a study examining people’s perceptions based on brief interactions. They found that people systematically underestimate other people’s opinion of them based on brief interactions. Generally, those perceptions were much better than people realized.

The problem is that conversations have become, as famed psychologist, Dr. Herbert Blumberg said, “conspiracies of politeness”. We hesitate to reveal our true feelings, and instead think we do people a service by being extraordinarily nice and safe in our conversations with them. In reality, our attempts at conversation aren’t actually attempts at conversation, but instead, attempts to be well liked.

There is indeed value in kindness, decorum and respect in everyday conversations. After all, it isn’t fun to deal with curt people, or have someone trauma dump on you, and reveal every horrible thing that has happened in their life.

People tend to enjoy going a little deeper with these conversations. During one study of people having interactions in a park, people revealed they were much happier when they had conversations that went relatively deeper (“relatively” being the operative word here), compared to more superficial conversations. They walked away feeling more connected with the person and grateful for having met them.

Some tricks to dive a little deeper

First, recognize that most people generally like you more than you think. This is important because our miscalculations about others guides what we do and don’t say in conversations. If we are overly fearful, we tend to be more guarded, feed into social anxiety, and spend time thinking about what we’ll say next rather than listening.

It tends to help if you dive deeper on major milestones of a person’s life, the things they likely have put much thought into.

The woman I was speaking with is a white collar lawyer, and briefly mentioned she was working long hours on a case. I asked, out of genuine curiosity, “So are you at liberty to share any of the details on this case?”

She said, “Oh absolutely, it’s public record now.”

She went on to elaborate — in impressive detail — the huge dispute between two oil companies, that were trading internationally and how they had a breakdown in their relationship over contractual details. It was a good old fashioned lawsuit over money, that she elaborated on like she had a PhD in this case alone. I could tell and appreciate why she was paid so well.

Asking these questions gets the other person talking, and most people love talking and being listened to. Doing this alone can help you really connect with someone and let go of all the difficult aspects of socializing.

It also does the other person a favor. They won’t leave the party feeling exhausted from answering the same 20 questions they’ve been asked their whole life. I know I generally hate having these superficial conversations. It’s also slightly dishonest to act like you are genuinely interested in some of these superficial answers if you aren’t.

Another trick is to avoid questions that can be answered in one word (such as “yes”, “no”, “not bad”). Make the questions more open ended, which will allow the other person to elaborate more.

One of my favorite tricks is to make someone laugh. Feel free to steal this joke. After someone tells you their name, ask them, “So did your parents name you that?”

It generally catches them off-guard and makes them laugh, mainly because of its absurdity. I had one guy, John, say with a deadpan face, “No that’s my stage name.”

And, personally, I would avoid talking about the weather, commenting, discussing, or asking a question about it. I generally think someone has given up on the conversation at that point.

So remember — avoid the conspiracy of politeness. If you want to have a conversation with someone, be genuine about having a conversation with them. Don’t go through a mental script of friendly things to say and ask, and spend the whole conversation planning your next move. Listen, and have the audacity to ask questions and go a little deeper.

Generally, we are subject to a liking gap: people like us more than we realize. Take advantage of that and make it a goal for the other person to walk away more satisfied too. You can’t do that by talking about the weather all night. And remember to avoid questions that can be answered in one word. That part is huge.

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Sean Kernan

I'm a nommer. Submit your articles to my publication Corporate Underbelly and I'll try to help you get boosted.