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(+1)

After I press play, they take off the OL shirt, and then nothing happens.

(+1)

That is when the game will try to load a save file. So maybe file access permission were denied.

What version of the game are running? desktop or html5?
What is your operating system and browser(if you used the html5 version on this page).

I am running html5 on chrome OS using chrome as my browser

(+1)

I never used chrome os before, I can only spitball potential issues.

Try changing the permission for this site. See if cookies and file editing is allowed.
https://support.google.com/chromebook/answer/114662

If that doesn't work, open the dev console and then play the game, see if there is any error log.
https://developer.chrome.com/docs/devtools/open/

If your chromebook is locked down and can't access the dev console, then I have no idea what to do.

Thanks for the help, I 100% complete the game (besides the 9999999 one). It is really good!

The 9999999 requirement is just the game making sure you will fail, because there is no content after that lol.