We consider the problem of learning in repeated games against arbitrary associates. Specifically, we study the ability of expert algorithms to quickly learn effective strategies in repeated games, towards the ultimate goal of learning near-optimal behavior against any arbitrary associate within only a handful of interactions. Our contribution is three-fold. First, we advocate a new metric, called disappointment, for evaluating expert algorithms in repeated games. Unlike minimizing traditional notions of regret, minimizing disappointment in repeated games is equivalent to maximizing payoffs. Unfortunately, eliminating disappointment is impossible to guarantee in general. However, it is possible for an expert algorithm to quickly achieve low disappointment against many known classes of algorithms in many games. Second, we show that popular existing expert algorithms often fail to achieve low disappointment against a variety of associates, particularly in early rounds of the game. Finally, we describe a new meta-algorithm that can be applied to existing expert algorithms to substantially reduce disappointment in many two-player repeated games when associates follow various static, reinforcement learning, and expert algorithms.