Yeah, I think that the DM will make sure that Cory regrets the directionless flaw.

DM: Okay, so you're in a straight hallway. Roll a d6 to determine which direction you'll go in.

Cory: But the door I need to go to is right there...

DM: Directionless flaw, remember.

Cory: *grumbles* okay, I got a six, now what?

DM: You go up.

Cory: What? Up?

DM: Yep, straight up. Through the roof and everything.

Also to add to the Zoro no sense of direction moments:

"They told us to go North, so I climbed up."