Embodiments described herein relate to establishing a privacy risk score between two datasets based on features common to the datasets. Methods may include: receiving a first dataset of probe data points defining a trajectory; receiving a second dataset of the probe data points defining the trajectory; identifying a plurality of features common to the first dataset and the second dataset; computing a privacy risk value for the identified features common to the first dataset and the second dataset; and computing an aggregate privacy risk score between the first dataset and the second dataset.