Recent advances in NLP have led to a rise in inter-disciplinary and application-oriented research. While this demonstrates the growing real-world impact of the field, research papers frequently feature experiments that do not account for the complexities of realistic data and environments. To explore the extent of this gap, we investigate the relationship between the real-world motivations described in NLP papers and the models and evaluation which comprise the proposed solution. We first survey papers from the NLP Applications track from ACL 2020 and EMNLP 2020, asking which papers have differences between their stated motivation and their experimental setting, and if so, mention them. We find that many papers fall short of considering real-world input and output conditions due to adopting simplified modeling or evaluation settings. As a case study, we then empirically show that the performance of an educational dialog understanding system deteriorates when used in a realistic classroom environment.