In General Relativity (GR), a free-falling object appears length-contracted to a distant observer as it approaches a black hole's event horizon, which raises questions about the nature of length and simultaneity in curved spacetime. The discussion highlights that length contraction is a relative effect observed from different frames, while tidal forces can cause stretching, complicating the interpretation of length in strong gravitational fields. Observers in different frames may define length differently, and the concept of length becomes ambiguous in curved spacetime compared to flat spacetime. It is emphasized that while GR extends the principles of Special Relativity (SR), the two theories operate under different assumptions regarding simultaneity and curvature. Ultimately, the complexities of measuring length and understanding contraction in GR reflect the nuanced interplay between gravity and the geometry of spacetime.