Surviving Monopoly: Mayfair, Jail, Repeat

Estimated time to read this post:

2–3 minutes

There’s chaos.

And then there’s the special kind of chaos that only happens when you play Monopoly with your family or closest friends.

And then there’s the special kind of chaos that only happens when you play Monopoly with your family or closest friends.

It starts innocently enough.

Someone’s rooting through the cupboard, finds the box, and says “fancy a quick game?”

Quick.

That’s the lie we tell ourselves every single time.

Three hours later, someone owns half of London, their other half has refused to pay rent on principle, and your partner’s been sent to jail for the fourth time. Not metaphorical jail. Actual Monopoly jail. Though at this point, the way tensions are running, metaphorical jail might be next.

The thing about Monopoly is it strips away all pretence of harmony.

That sweet lovely person who bakes biscuits? They’re now a property tycoon with zero mercy, putting hotels on Mayfair just to watch you suffer. “That’ll be £2,000, love.” They’re not even looking at you. They’re counting their money. They’ve got a system.

And someone always flips the board. Always. Usually around the two-hour mark when they land on Park Lane for the third time and realise they’re financially ruined by a game that’s meant to be fun.

“This is RIGGED!” they shout, in pure angst.

Then there’s the banker who always gets accused of embezzlement.

“You’ve been helping yourself to extra cash, haven’t you?”

“I’M THE BANKER. I’M LITERALLY HANDLING THE MONEY. THAT’S THE JOB.”

Doesn’t matter. Trust is gone. Someone suggests an audit. For Monopoly money.

The rules become… they become…umm…flexible.

“Actually, I think Free Parking means you get all the tax money.” “No it doesn’t.”

“Yes it does.” “Show me in the rules.” Nobody can find the rules.

The rules disappeared in 1997.

We’re operating on vibes and half-remembered instructions from childhood.

And the properties! The negotiating!

“I’ll give you Whitechapel for Old Kent Road and £500.” “That’s highway robbery.” “It’s called capitalism.” You’re suddenly having full-blown business meetings over streets that don’t even exist in the configuration the board suggests.

Often someone goes bankrupt in the first 30 minutes and then has to sit there watching everyone else play for the next two and a half hours. They’re not allowed to leave. That’s the rule. You started this game together, you’ll finish it together.

Even if “together” means one person scrolling their phone in silent resentment.

The game only ends in three ways:

  • someone wins (rare),
  • someone flips the board (common),
  • or everyone mutually agrees to abandon it and never speak of it again (most common).

The box goes back in the cupboard. We’ll do this again next year. We’ll have forgotten the trauma by then.

If you’ve ever mortgaged everything they own to avoid landing on Mayfair with a hotel, remember – you’re not alone.

We’ve all been there.

We’ve all made terrible financial decisions over fake money.

That’s what Monopoly does to you.


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