An improved system and method for disambiguating text strings labeling content objects is provided. A text string set may be received from a user. Frequencies of co-occurring text strings in a text collection may be obtained, and a disambiguation measure may be determined for a pair of text strings that each co-occur with a text string in the text string set. The disambiguation measure may be based on a weighted KL divergence of text string distributions that maximizes the value of divergence when a text string set may occur in different contexts. A disambiguation measure may be determined for a list of the top most common pairs of text strings that co-occur with the text string set, and the pairs of text strings may be output in decreasing order by disambiguation measure for those pairs of text strings with a disambiguation measure that exceeds a threshold.