Voting Advice Applications have been subject to equal measures of praise and condemnation. To some they represent a natural evolution to an increasingly pervasive—and perhaps even (artificially) intelligent—new media. To others they are indicators of Western society’s Orwellian trajectory. In any case, the normative implications of Voting Advice Applications warrant careful scrutiny, particularly in light of speculation regarding their potential effect on voter behaviour and, consequently, electoral fortunes. This paper draws on the experience of Vote Compass to critique the norms and methods commonplace in the design of VAAs in the European context. It posits and tests alternatives to conventional modes of representing alignment with candidates. It also speaks to both the theoretical and methodological advances in the area of Big Data that enable certain VAA datasets—which are universally self-selected samples—to be treated in such a way as to make representative inferences about their corresponding populations.