The past 100 years of empirical research in ecology have generated tremendous knowledge about the component interactions that structure ecological communities. Yet, we still lack the ability to reassemble these puzzle pieces to predict community responses to perturbations, a challenge that grows increasingly urgent given rapid global change. We summarize key advances in community ecology that have set the stage for modeling ecological systems and briefly review the evolution of ecological modeling efforts to identify critical hurdles to progress. We find that while Robert May demonstrated that quantitative models could theoretically predict community interactions nearly 50 years ago, in practice, we still lack the ability to predict ecological outcomes with reasonable accuracy for three reasons: (1) quantitative models require precise data for parameterization (often unavailable) and have restrictive assumptions that are rarely met; (2) estimating interaction strengths for all network components is extremely challenging; and (3) determining which species are essential to include in models is difficult (model structure uncertainty). We propose that fuzzy interaction webs (FIW), borrowed from the social sciences, hold the potential to overcome these modeling shortfalls by integrating quantitative and qualitative data (e.g., categorical data, natural history information, expert opinion) for generating reasonably accurate qualitative predictions sufficient for addressing many ecological questions. We outline recent advances developed for addressing model structure uncertainty, and we present a case study to illustrate how FIWs can be applied for estimating community interaction strengths and predicting complex ecological outcomes in a multitrophic (plants, herbivores, predators), multi‐interaction‐type (competition, predation, facilitation, omnivory) grassland ecosystem. We argue that incorporating FIWs into ecological modeling could significantly advance empirical and theoretical ecology.