Optical characteristic measuring systems and methods for determining the color or other optical characteristics of teeth comprising a probe body (2) wherein the probe provides light to the surface of the object (20). Perimeter receiver fiber optics (102) are spaced apart from a source fiber optic and receive light from the surface of the object (20) being measured. Light from the perimeter fiber optics passes 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 being measured wherein the numerical apertures of the receiver fiber optics are different.