First day in the Army Aviator Fixed-Wing Course, doing a walk-around pre-flight with a student, on a Cessna L-19 Birddog.
(basic airframe of a Cessna 180)
After walking around the tail, I'm leading him up the side of the fuselage towards the cockpit door (under the wing), and he walks straight-up into the trailing edge of the flap. Smacked him straight across the forehead right between the hairline and eyebrows. Didn't cut, but made a sharp red line.
I stepped out, crouched down under the wing, and asked him, "Did you hurt it?" (looking intently at the possible cut)
He stepped back, looked intently at the trailing edge of the flap, reached up and squeezed it between his fingers, and said, "No, I don't think so, Sir."