"Money isn't the point of life"
There's a belief that sits above all the others, and it sounds wise. Money isn't what matters. Friends matter, experiences matter, the children matter. A person who counts the pounds at the table has their priorities wrong, and this book, with its question about price, is asking you to become that person.
I'd turn it round. Consider what keeping up requires. It requires knowing what everyone at the table spends, and matching it. It requires noticing the neighbour's kitchen and the colleague's car and the school-gate trainers. It requires, in practice, thinking about money nearly all the time, in the form of what other people have and what you'd need to have the same. The person keeping up isn't the one who's put money in its place. They're the one who's put it at the centre and called it friendship.
Tim Kasser and Richard Ryan, in 1993, found across three studies that people for whom financial success was a central aspiration, relative to other things they wanted from life, had lower wellbeing and, in a non-student sample, were rated as less well adjusted by interviewers. Helga Dittmar and colleagues, in a 2014 meta-analysis of over two hundred and fifty samples, found that a materialist orientation went with lower wellbeing, with the strongest links to risky spending and to how people felt about themselves. Both are correlational. Materialism might follow unhappiness rather than cause it. But the direction is consistent, and an earlier book in this series uses the same finding with the same warning.
What matters here is what materialism is in those studies. It isn't liking nice things. It's having money and possessions near the centre of what you want, and measuring yourself by them. Keeping up is exactly that, in disguise. The person who says "money isn't the point" while splitting a bill they can't see, matching a kitchen and buying trainers for the school gate has money at the centre. They've just arranged not to look at it.
The question in this book, asked before each yes, is the opposite of money at the centre. It puts the price in view for ten seconds so that it can be dealt with and then dropped. A person who asks the price and then decides is a person for whom money was a small, brief consideration. A person who never asks and matches everything is a person for whom it's the weather.