These are some actual sentences I produced yesterday.
First, the first thing out of my mouth when my friend picked up the phone:
I should take which direction to the airport?
That shouldn't be a wh-in situ question if I'm not echoing something previously said, and how can I be echoing something previously said if the conversation is just starting? I broke pragmatics with this one.
Second, referring to my worry about going up a hill in the wrong direction:
I'm just scared I'll drive it up the wrong way.
Um, that's a verb plus a prepositional phrase, not a verb-particle. I broke syntax with this one.
Third, and this one is so shockingly against all the rules of English grammar that it needs no context:
What should I drive past a?
A hideous, and egregiously wrong, blend of "What should I drive past?" and "I should drive past a what?" I think I just broke the English language with this one.