We propose a new variant of online learning that we call "ambiguous online learning". In this setting, the learner is allowed to produce multiple predicted labels. Such an "ambiguous prediction" is considered correct when at least one of the labels is correct, and none of the labels are "predictably wrong". The definition of "predictably wrong" comes from a hypothesis class in which hypotheses are also multi-valued. Thus, a prediction is "predictably wrong" if it's not allowed by the (unknown) true hypothesis. In particular, this setting is natural in the context of multivalued dynamical systems, recommendation algorithms and lossless compression. It is also strongly related to so-called "apple tasting". We show that in this setting, there is a trichotomy of mistake bounds: up to logarithmic factors, any hypothesis class has an optimal mistake bound of either Theta(1), Theta(sqrt(N)) or N.