Temporomandibular disorders (TMD) represent a significant health concern, potentially affecting patients’ quality of life, reducing work efficiency, and leading to absences or limitations in daily activities. Consequently, it is essential not only to apply accurate diagnostic and therapeutic approaches for individuals with TMD and/or sleep bruxism (SB) but also to examine how various medical and lifestyle factors influence the development of these conditions, as adjusting these factors could alleviate symptom severity. This preliminary study aimed to explore the associations between SB, self-reported pain and headaches, specific health factors, and overall health status in patients with TMD. The study involved 114 patients from the Outpatient Clinic for Temporomandibular Disorders in Wroclaw, Poland, who underwent single-night video-polysomnography (PSG). Participants completed questionnaires addressing their pain experiences, headaches, and health status, including the presence or history of conditions such as hypothyroidism, hypertension, cancer, diabetes, myocardial infarction, stroke, and gastroesophageal reflux disease (GERD). Information on lifestyle habits—including alcohol consumption, smoking, caffeine intake, and physical activity—was also collected. All data were subjected to statistical analysis. Among TMD patients, a history of cancer and GERD appeared to influence the perception of pain and headaches. Additionally, smoking was significantly correlated with both the presence and severity of SB. Certain lifestyle habits, health factors, and overall health conditions in TMD patients are linked to SB, as well as reported pain and headaches. However, these relationships warrant further investigation in studies with larger sample sizes.