The present observational prospective study analyzes the eating habits in association with the medico-oral health of catering workers, since they seem the category at higher risk of developing dental problems. Objective: To evaluate oral and medical health through a questionnaire in a total sample of 603 participants. Additionally, this article aims to provide information regarding the medico-oral implications of an unbalanced diet linked to this particular profession. Material and methods: A questionnaire created through Google Forms platform was sent to all members of the Italian Federation of Chefs (FIC). The mean age was 46.9 ± 32.6 ranging from 17 to 66 years old. Results: Catering workers’ years of service showed a significant impact on the presence of teeth pain (p < 0.05), missing teeth (excluding the third molars) (p < 0.01), treatment with prothesis (p < 0.01), dental fillings (p < 0.01), dental extractions (p < 0.01), diabetes (p < 0.05), high blood pressure (p < 0.01), joint pain (p < 0.01), back pain (p < 0.01), neck pain (p < 0.01), and gastroesophageal reflux (p < 0.05). Conclusions: A conspicuous part of the study sample was overweight, with a high BMI. Moreover, the years of service in this field showed significant impact on dental problems. Therefore, a very important role is that of preventing dental problems and giving information on the causes and effects unknown to many workers in the sector.