A ubiquitous learning problem in today’s digital market is, during repeated interactions between a seller and a buyer, how a seller can gradually learn optimal pricing decisions based on the buyer’s past purchase responses. A fundamental challenge of learning in such a strategic setup is that the buyer will naturally have incentives to manipulate his responses in order to induce more favorable learning outcomes for him. To understand the limits of the seller’s learning when facing such a strategic and possibly manipulative buyer, we study a natural yet powerful buyer manipulation strategy. That is, before the pricing game starts, the buyer simply commits to “imitate” a different value function by pretending to always react optimally according to this imitative value function. We fully characterize the optimal imitative value function that the buyer should imitate as well as the resultant seller revenue and buyer surplus under this optimal buyer manipulation. Our characterizations reveal many useful insights about what happens at equilibrium. For example, a seller with concave production cost will obtain essentially 0 revenue at equilibrium whereas the revenue for a seller with convex production cost is the Bregman divergence of her cost function between no production and certain production. Finally, and importantly, we show that a more powerful class of pricing schemes does not necessarily increase, in fact, may be harmful to, the seller’s revenue. Our results not only lead to an effective prescriptive way for buyers to manipulate learning algorithms but also shed lights on the limits of what a seller can really achieve when pricing in the dark.