Its interesting to note that there are several phrases that are understood to mean something other than what the words mean. For example

Bookmaker (is not a maker of books)

Planning Permission (You need permission to build not plan)

Bank Holiday (understood to mean public holiday in the UK)

Any others you can think of?

Well, according to some dictionaries, 'literally' also means 'figuratively' because of all those people who scream at Justin Bieber concerts "I'm literally dying right now!" (Of course, if I was at a Bieber concert, I would be literally dying...)

Lol, Uff-da, Caeli! it's ok, I'd probably be dying too...

I think of things like bass (the fish), bass (the instrument), and base.

As well as lead (the metal) and lead (to lead something).

Or even how we put cargo on ships, shipments on cars, drive in parkways and park in driveways...

I've been trying to help one of my Japanese friends with his English, and he's been teaching me Japanese. Every once in a while, he apologizes for how difficult Japanese is, to which I usually reply with how confusing English is...

LOL, yeah...don't get me started on Bieber.

And those would be homophones, which aren't really the same thing. But the cargo/shipments/drive/parkways thing. Yeah, totally agree.

I think it would be so fun to have a friend whose native language is not English. I can just imagine all the weird conversations to be had!

Parking in the drive way, and driving on the parkway.

I don't hold that the reverse use of the term 'literally' is acceptable.

Being a portuguese speaker I can tell you guys how english can be confusing too xD

One thing that make every english leaner crazy are the cognates(words that have similar spelling and same meaning) and false cognates(words with similar spelling but totally different meaning).
Example:
College is similiar to "Colégio" but the correct translation is "Faculdade" ("colégio" around here is the middle-high school meaning).