Dieting is a behaviour change task that is difficult for many people to conduct successfully. This is due to many factors, including stress and cost. Mobile applications offer an alternative to traditional coaching. However, previous work on apps evaluation only focused on dietary outcomes, ignoring users’ emotional state despite its influence on eating habits. In this work, we introduce a novel evaluation of the effects that tailored communication can have on the emotional load of dieting. We implement this by augmenting a traditional diet-app with affective NLG, text-tailoring and persuasive communication techniques. We then run a short 2-weeks experiment and check dietary outcomes, user feedback of produced text and, most importantly, its impact on emotional state, through PANAS questionnaire. Results show that tailored communication significantly improved users’ emotional state, compared to an app-only control group.