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(5 edits)

Updated Guide.

TL;DR

/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"
brew install --cask wine-stable
cd ~/Downloads/YourOnlyMoveIsHUSTLE
wine64 YourOnlyMoveIsHUSTLE.exe

Thorough guide:

0. Open Terminal
Open Terminal by using the Spotlight Search through Cmd + Space, then type Terminal

1. Get Homebrew for Mac

https://brew.sh/

/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

2. Install Wine

https://formulae.brew.sh/cask/wine-stable#default

brew install --cask wine-stable

Note: this step is different from laurasnow because it does not need to install homebrew-cask-versions, which allows for installing older, deprecated versions of wine. which we do not need, as we are grabbing the current `wine-stable` version 8.0 anyway

Alternate route through a helper wizard: https://www.embird.net/sw/embird/tutorial/wine/wine.htm

3.  cd into the Your Only Move Is HUSTLE folder

cd ~/Downloads/YourOnlyMoveIsHUSTLE

4. Run wine

wine64 YourOnlyMoveIsHUSTLE.exe

Sanity checks:

* Check if homebrew is downloaded

which brew
> /opt/homebrew/bin/brew
brew --version
> Homebrew 3.6.21
> Homebrew/homebrew-core (git revision a63a7493134; last commit 2023-02-15)

* Check if wine is installed

which wine64 
> /opt/homebrew/bin/wine64 
wine64 --version 
> wine-8.0

* Check to see if current directory in Terminal is correct

Print Current Working Directory ( pwd ), and list files ( ls )

pwd
ls 

* Check to see if you have an older Mac before 2018 or before MacOS Mojave, use wine instead of wine64

* Check to see if you have Apple Silicon for your Mac

According to wine version 7.0, 

The new Apple Silicon Macs are supported, including running x86-64 binaries under Rosetta 2.

You have to use wine64 and also you need to install Rosetta 2.

* Check to see if you allow unverified developer programs to be run and have Gatekeeper disabled

Follow guide here https://www.makeuseof.com/how-to-disable-gatekeeper-mac/

Notes:

 Worked first try after disabling Mac Security Gatekeeper. Thanks Laurasnow. I've always been to scared to try out wine so I am glad it was such a painless process! I would be glad if you updated the original post with the sanity checks.