Does it give any error messages?
When open it not in the terminal, it just says it closed and when I try to open it in the terminal, it says:
[0509/210504.916161:ERROR:file_io.cc(89)] ReadExactly: expected 8, observed 0
[80720:45827:0509/210505.042768:ERROR:browser_gpu_channel_host_factory.cc(120)] Failed to launch GPU process.
[80720:45827:0509/210505.120020:ERROR:service_manager_context.cc(252)] Attempting to run unsupported native service: /Users/ME/Downloads/Lust Doll Plus r37.2 (Mac)/Game.app/Contents/Versions/65.0.3325.146/nwjs Framework.framework/content_renderer.service
Edit: also, I found out that I can play it in browser (ed2: using newgrounds), so I can just do that.
I just gave up after trying the first 3 solutions and doing the simple chmod which is just chmod +x Contents/MacOS/nwjs not using the sudo stuff. Winebottler doesn't work well with my mac. I am currently playing on the newgrounds version, so no further assistance will be necessary. Thanks for the help.