Prediction‐based processes appear to play an important role in language. Few studies, however, have sought to test the relationship within individuals between prediction learning and natural language processing. This paper builds upon existing statistical learning work using a novel paradigm for studying the on‐line learning of predictive dependencies. Within this paradigm, a new “prediction task” is introduced that provides a sensitive index of individual differences for developing probabilistic sequential expectations. Across three interrelated experiments, the prediction task and results thereof are (...) used to bridge knowledge of the empirical relation between statistical learning and language within the context of nonadjacency processing. We first chart the trajectory for learning nonadjacencies, documenting individual differences in prediction learning. Subsequent simple recurrent network simulations then closely capture human performance patterns in the new paradigm. Finally, individual differences in prediction performances are shown to strongly correlate with participants’ sentence processing of complex, long‐distance dependencies in natural language. (shrink)