Hey, here's the troubleshooting I've gathered for Mac issues. You can see if anything here works for you!

Prisoner (itch) (deacoz) mac os catalina

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On Mac: The application 'Game' can't be opened/ Game cannot be launched
Some things you can try:

- Hold the Control key while opening the game

- Go to 'System Preferences > Security & Privacy', and change your options to allow apps downloaded from anywhere. https://support.apple.com/en-ca/HT202491

- Download the Windows version. Download the latest version of nwjs (http://nwjs.io/downloads/). Copy and paste the nwjs files into the Windows version folder, overwriting what's inside. Run the game using the executable in the nwjs files.

- Same as above, but use nwjs 0.45.6 instead.

Prisoner (itch) (deacoz) Mac Os X

- Download the Windows version. Download and install Wine + WineBottler. Run the Game.exe and library files through WineBottler to produce a Game.app. Run Game.app

- Run the game using the following commands:
chmod +x Game.app/Contents/MacOS/nwjs
chmod +x Game.app/Contents/Frameworks/nwjs Helper.app/Contents/MacOS/nwjs Helper
chmod +x Game.app/Contents/Frameworks/nwjs Helper EH.app/Contents/MacOS/nwjs Helper EH
chmod +x Game.app/Contents/Frameworks/nwjs Helper NP.app/Contents/MacOS/nwjs Helper NP

Detailed chmod +x instructions:
(Thanks to Night Star for this solution!)
To fix 'Game cannot be launched', you must change two files within the 'Game' files into executables.
-Right click the 'Game' icon and click the option 'Show Package Contents'.
-Go into the 'Contents' folder, then the 'MacOS' folder. Look for the file 'nwjs'.
-Open up Terminal and type 'chmod +x ' making sure to add a space after x.
-Grab the 'nwjs' and drag it into console. If you do it correctly, it will look like this in console:

chmod +x /Users/[user]/Desktop/Lust Doll Plus r17.2 (Mac)/Game.app/Contents/MacOS/nwjs '

-Hit enter and the 'nwjs' file with become an executable.

-Next, go into the 'versions' folder, and then a folder with a string of numbers, something like '65.0.3325.146'
-Right click 'nwjs helper' and click 'show package contents'
-Go into the 'contents' folder, then the 'MacOS' folder, and you will see the file 'nwjs helper'.

Prisoner (itch) (deacoz) Mac Os Update

-Repeat the above steps to turn this file into an exectuable, similar to what you did with the 'nwjs' file.

-Hold Control when launching the game!