This paper introduces the problem of automatic font pairing. Font pairing is an important design task that is difficult for novices. Given a font selection for one part of a document (e.g., header), our goal is to recommend a font to be used in another part (e.g., body) such that the two fonts used together look visually pleasing. There are three main challenges in font pairing. First, this is a fine-grained problem, in which the subtle distinctions between fonts may be important. Second, rules and conventions of font pairing given by human experts are difficult to formalize. Third, font pairing is an asymmetric problem in that the roles played by header and body fonts are not interchangeable. To address these challenges, we propose automatic font pairing through learning visual relationships from large-scale human-generated font pairs. We introduce a new database for font pairing constructed from millions of PDF documents available on the Internet. We propose two font pairing algorithms: dual-space k-NN and asymmetric similarity metric learning (ASML). These two methods automatically learn fine-grained relationships from large-scale data. We also investigate several baseline methods based on the rules from professional designers. Experiments and user studies demonstrate the effectiveness of our proposed dataset and methods.