Empty Trash (Monterey OS)

Give this a try: boot into Safe Mode according to How to use safe mode on your Mac and test to see if the problem persists. Reboot normally and test again.

NOTE 1: Safe Mode boot can take up to 3 - 5 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files

NOTE 2: if you have a wireless keyboard with rechargeable batteries connect it with its charging cable before booting into Safe Mode. This makes it act as a wired keyboard as will assure a good boot into Safe Mode.

Please read the following user tip and restate your question/problem in detail: 

     Writing an Effective Apple Support Communities Question - Apple Community

Where are you seeing the "skip" option? Can you post a screenshot of it and under what conditions?

When I click on the Trash Can and select "Empty Trash", this box comes up. And the only way to empty my traush is to click on "Skip"