Red Flag: Monopoly

The progression of my relationship with the board game Monopoly:


I played this game as a young child. A young child undoubtedly unprepared for the mental strain of this game. I was also the youngest in my family so I was the most unprepared person playing it.

The games stretched on. I have memories of playing this game on the floor with my sister using a space underneath a propped up skateboard to keep my deeds organized. Eventually, the boredom and frustration would set in.

Inevitably, I would lose track of the game. I would forget what I was doing, what all of the rules were, what part of the game we were actually playing at that time. I would be downhill from there.

I would never win. Or come close to winning. I have literally never won a single game of Monopoly in my entire life. Even the games that weren’t finished ended with me not in the lead.

Strained Acceptance

As I got older, I would assure myself that Monopoly was an amazing game. I just wasn’t that good at it. Perhaps, I needed to play it more to really come to terms with the brilliance of this classic game.

I clung to the idea that it was just me being inept this entire time to try to salvage my faith in this endless, utterly boring game.

It didn’t last


I didn’t play Monopoly much as a teenager and young adult. But around the time my undiagnosed ADHD would cause me to lose all focus, I would simply entertain myself. By cheating. Here’s some of my usual moves:

  • Passing GO! and taking two $500 bills, instead of $100 bills. Making my reward for reaching that point $1,000 instead of $200.
  • Landing on one place and taking the deed to another property.
  • “Funny” counting methods for moving my token across the board that meant I always landed on good spots, even when the math didn’t work out.
  • Counting out fines and fees then handing over the incorrect sum to the banker.
  • Volunteering to be banker and casually paying myself out more and more money as the game progressed (or, well, didn’t progress).
  • I once took someone else’s piece and made two turns before they realized what I had done.

I should mention that we purchased a Pokemon Monopoly game at some point and as a loyal TV show devotee, I was the only one playing who knew the Pokemon. It made it much easier to cheat when everyone else couldn’t tell a Charizard from a Pikachu.


Finally, I just stopped playing the game at all. I realized, I had no real positive associations with it. I had played it, sure. But I never remembered a time where I had enjoyed playing it. Other than some hilarious cheating and that wasn’t even supposed to be part of the game.

Once I allowed myself to accept that I just didn’t like this game, I came to terms with how much I just didn’t like it.

Red Flag!

In 2017 I was considering dating a man who once texted me that he was having a great time playing a game of Monopoly with a bunch of his adult friends. We didn’t end up dating for a variety of reasons, but the fact that a grown-ass adult claimed to enjoy playing this game with other grown-ass adults, when they could have literally played anything other than Monopoly, was entirely too much for me.


To my imaginary audience, who might be offended that I have no love for the game of Monopoly and tarnish its name so flagrantly.

Shhhh…… Shhhhh….. it’ll all be okay in the morning.