Optical characteristic measuring systems and methods for determining the color or other optical characteristics of teeth comprising a probe body (
) wherein the probe provides light to the surface of the object/tooth (
). Perimeter receiver fiber optics (
) are spaced apart from a source fiber optic and receive light from the surface of the object/tooth (
) being measured. Light from the perimeter fiber optics pass to a variety of filters. The system utilizes the perimeter receiver fiber optics (
) to determine information regarding the height and angle of the probe with respect to the object/tooth being measured wherein the numerical apertures of the receiver fiber optics (
) are different.