What to say when someone says “guess what”

1 min readSep 9, 2022

When someone is trying to impress you, let them.

Guess under expectation.

That’s what they want you to do. When they say, “guess how much I got these shoes for!” and they are implying that they got a great deal, don’t guess five dollars. Guess forty dollars so that they can impress you by revealing that it was only twenty!

When someone says, “my boss just got a new car, guess how much”, it’s the opposite. Don’t guess super high, like two hundred thousand dollars. Guess a bit lower than you expect, like fifty thousand.

A friend of mine taught me this years ago, and most people miss unwritten social contract and end up disappointing people instead of joining in their amazement.

More examples:

> “Guess how long I was stuck in traffic, ugh”

Don’t say “5 hours????”
Do say: “40 mins?”

> “You wouldn’t believe how old the oldest person who ever lived was”
Don’t say “200 years old?”
Do say “102?”

The key idea here is when someone is trying to impress you, let them.

Don’t redirect the conversation to you trying to impress them with your amazing powers of accurate guessing.




Most of my writing is about software. I enjoy summarizing and analyzing books and self-help videos. I am senior software consultant at LazerTechnologies.com.