Single Person's Guide to Expired Milk
Tip 1 - Don't order your milk from overseas. Not all the containers are refrigerated. Or shielded from mutating cosmic rays. Plus it might not be non-GMO and we can't have that.
Tip 2 -
If it smells a little off - okay to risk it.
If it tastes a little off - probably not okay to risk it.
If it's gained sentience and wants to destroy all human life - don't risk it. UNLESS you're eating Captain Crunch. Captain Crunch is basically mouth shrapnel without milk.