People love to pick on the intensive meaning of "literally", perhaps because it is more recent, but it's really not much different from the range of uses of "re

People love to pick on the intensive meaning of "literally", perhaps because it is more recent, but it's really not much different from the range of uses of "really", which also can mean both 'in fact, truly' as well as an intensifier sense like 'very'. E.g. "I was really shocked", "I was literally shocked" have similar ambiguities. Competent human speaker generally provide enough context that potential ambiguities aren't too problematic -- for other human beings, if not for machines. Human languages are more ambiguous than you might imagine, and lexical things like 'what meaning of "literally" is the speaker using' are pretty tip-of-the-iceberg stuff. (Think about what "Every man wants to read some book" or "the girl saw the man with the binoculars" (can) mean.)