This paper presents a methodology for studying pedestrians' behavior at pedestrian crossings. The developed mathematical models are empirically tested using pedestrian data collected at a number of pedestrian crossings in Amman. Estimated models include waiting time at the curbside and the number of crossing attempts needed by the pedestrian to make a successful crossing. From a broad range of road user and roadway factors, the strongest and most significant predictors which influenced the pedestrian's waiting time (delay) and the frequency of attempts to cross the streets were gender, age, number of children in household, crossing frequency, number of people in the group attempting to cross, access to private vehicle, destination, home location in relation to pedestrian crossing, and pedestrian past involvement in traffic accidents. In addition to these predictors, maximum likelihood estimates revealed that the pedestrian expected waiting time seems to profoundly influence the number of attempts needed to successfully cross the street.