If you were in freefall from a jet airplane, would the airplane overtake you in the fall (assuming that the plane started freefalling as you jumped out the door)?
It would overtake you immediately. Airplanes are designed to experience extremely small drag forces and are remarkably aerodynamic as a result. In contrast, you would experience severe air drag (air resistance) once you left the plane. The plane would coast past you at high speed while you would slow enormously in the first second or two of exposure to the air.