Some of the most cutting edge and effective web performance optimizations, like prefetch and preconnect, involve being proactive. We make predictions to determine where a user is likely to go next and load resources ahead of time so page load is as fast as possible. This is where machine learning comes in handy. By training a machine learning model (maybe a markov chain?) with current analytics data, we can take the guess work our of our predictions and more accurately load resources ahead of time. In this talk, we will examine techniques currently being developed, like GuessJS to make predictive prefetching a reality.