I'm a psychologist who studies conversation, and I think this is all good advice! Extending the invitation is especially important––it boggles my mind how often those invitations seem to go un-extended in conversations, and how people blow past what's most interesting and important.

One thing I disagree with, though, is that most conversations between new acquaintances are bad. We find pretty consistently that people *expect* them to be bad, but once they have them, people report them being pretty great. For instance, in one of my studies, people talking to a stranger in the lab gave their conversations over a 5 out of 7, on average: https://www.pnas.org/doi/10.1073/pnas.2011809118.

In another study, some of our friends found that people expected conversations with strangers to be worse than they actually were (and they were pretty good): https://psycnet.apa.org/doiLanding?doi=10.1037%2Fa0037323

This is part of an emerging literature where we're finding that people underestimate just how well their conversations go. For instance, people tend to think that the people they meet like them less than they actually do: https://journals.sagepub.com/doi/pdf/10.1177/0956797618783714?casa_token=nMA1QY9X2D8AAAAA:BpJyUAPVQ-fOXijtaqrLJMM9B4532cjdWeQZrOd_8yOteV7Z1O8Ytsmbcaj3auVs_PWByhLsX97gkA

This is true also when people meet each other in groups––they think they're the least-liked of the group, on average: https://www.sciencedirect.com/science/article/pii/S074959782030399X?casa_token=pEaqKi8bMN4AAAAA:lKP54mncTCqXEGp5aoFVxx701dobXcewa0287OwCD9hyMkCAyrfLvhFwouhU0MJVx1yvwlik4bY

And it's even true for kids: https://journals.sagepub.com/doi/pdf/10.1177/0956797620980754?casa_token=N7Slf_AI4ukAAAAA:eXCpTMLdXHmP69lJr3pm06fm1XNdoVT9YrUUcjIjcvN76N1j4iy2EDBGuDGYoI0HQtg5eRlygYYemA

Coming out of all this, I've also got some ideas about what makes a good conversation: https://experimentalhistory.substack.com/p/good-conversations-have-lots-of-doorknobs

Anyway, talking to other people is probably the single most important thing that people do, and it deserves some deep thinking. I think you're especially right that conversations are so contextual that they can't be abstracted––at least, not yet!

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Jul 29, 2022Liked by Sasha Chapin

This is good/weird/specific enough that I can see it being used by some advanced AI robot to mimic human interaction.

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The #1 thing that changed my small talk game was getting a dog. I'm generally very shy, but with a dog you invariably end up talking to other dog parents, and these conversations feel easy because the dogs provide an obvious thing to talk about--you can chat about their breed, age, energy level, favorite toys and treats, etc. Now that I've had all these positive interactions with strangers, I'm less nervous about small talk in general.

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Silence is brilliant. Andrew Callaghan, when he interviewed people for his gonzo Channel 5 program, would always wait a few seconds after his subject gave their answer. To break the silence, perhaps in a sort of panic, they'd follow up with a sort of second answer. This would always be more interesting than the first. Then the conversation really got going.

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my new goal in conversation

an intention to become relaxed and open

porous boundaries - let the other person lead but feel how my boundaries change during the convo and

go from that

try not to hyperfocus during the conversation because it takes me out of it. it's natural for me to get completely absorbed when i am talking but this isn't what i want with new people. so, i wear my hyperfocus monitor, and relax my way out of it, if i can, if i find myself doing it.

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This is the best post I've ever read on having good conversations. As an extreme extrovert, I've been practicing this my whole life and never read someone who put what I discovered into words before.

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Love your stuff, Sasha. The intentionality and lucidness with which you approach life is inspiring. Please keep writing :)

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Wonderful post chockablock with excellent advice.

One idea that I’ve found very helpful for me is to approach conversations with a playful and experimental stance (appropriate to the situation). As opposed to you know treating every conversation as if you’re loading nuclear fuel into a reactor or something.

Also, for people with significant social anxiety, check out the Ovrcome app that uses VR exposure to make things easier.

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Ben Kuhn's post contains a suggestion that's very similar to a piece of advice I recently got from a friend. My friend is great at being engaged when interacting with people, and I recently interviewed him in order to learn what he's doing.

His suggestion is to try to model the other person - things that are salient to them, their frames of reference, what's important to them and why, etc.

I tried it out, and found it very helpful. It drives me to engage in the conversation, seeking patterns that tell me more about how the other person functions. It also helps me remember people vividly - it's easier to remember a coherent system with an organizing principle, rather than a bunch of facts.

Right now I'm playing with a very direct approach, telling people that I'm trying out a new method of getting to know people quickly, and asking them if they are open to experiment. If they are, I ask them "what's important to you?". Most people absolutely adore this question! It opens up for fertile avenues of further exploration - figuring out the backstory, where things are going, etc.

This approach functions well in 1-on-1 conversations, but I'm hesitant to try it out in group settings, due to the skew in group focus combined with an unwillingness to put someone on the spot in front of a crowd. So I'm exploring less direct approaches, trying to find one for group settings.

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Really enjoyed this post, keep it up =)

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Love this all, this especially stuck out to me as it's a disagreement I've had with so many —

"Some people get frustrated with small talk because the words themselves are not enlightening. But they’re focusing on the wrong thing..."

I ADORE small talk. Not cause I actually care-care that you live in Evanston, went to Boston College, or are a biracial only child raised by a single mom, but because we're opening doors to connection and conversation both in sharing facts and persona.

Thank you for this musing Sasha, so enlightening! Evernote'ing to share in my Adulting Kit and workplace workshops and to my general community at large.

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Hi Sasha, I really enjoyed reading this. So much of what you said resonated with me. Human connection is also one of my favorite things. To me, it makes life so much richer and exciting. I'm also genuinely curious about a lot of things and other people. I've been experimenting how to better connect with people and I've had decent success. However, I'm always looking to improve on this skill, so I'm curious, do you have any resources you might suggest looking into (books, blogs, articles, courses, etc...) that might help to develop better conversation skills, specifically developing connection? Thanks!

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This is really good.

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