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What’s The Worst Question to Ask?

Extroverting by Brandon Possin
6 min readAug 26, 2023

We want to show interest in someone. We want to open a conversation. We want to come across as friendly. We want to enjoy the moment with someone special. Yet we prevent a good conversation when we ask a common question:

“How are you?”

It’s the worst question to ask.

Variations of this include “How + [to be verbs] + time frame” style questions. How was your day? How are you doing now? And the question that earns the most eye rolls on online dating app chats: “How was your weekend?”

I know, conventional wisdom would make us think it’s a great way to open up a chat. This article will probably draw out plenty of people who disagree with this. So why is this such an unhelpful question?

It Demands Us to Choose an Adjective…

Asked how we are doing, we have to travel back in time 1–2 days and consolidate dozens of situations and moods into an adjective that summarizes all those moods. It can be mentally taxing to put many situations through a mental filter and come out with the right word.

“How are you” is such a broad question, the answerer doesn’t know where to turn. Which part of our days do we highlight? And what do we share to this particular person, given we won’t share with our co-workers the same content as with a best friend. It’s a mental load to carefully calibrate what we share in an answer. Tiring, right?

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Extroverting by Brandon Possin
Extroverting by Brandon Possin

Written by Extroverting by Brandon Possin

Blog on making the most of opportunities, especially in emerging tech and being extroverted. By the founder of a science fintech startup in Japan, Merito.

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