A system and method for automatically grouping items, e.g., digital photographs, by analyzing the statistical distributions of at least one piece of information associated with each of the items, for instance, creation time, are provided. In one embodiment, the creation time may be converted into a numeric value and the numeric values placed in ascending order such that gaps between adjacent numeric values may be determined. Subsequently, a median difference may be determined as well as an optimum difference. The items may then be organized into groups such that an additional group is created each time the difference between the numeric value for an item and the numeric value for the adjacent item located therebelow in the ascending array is greater than the optimum difference.