Background The relationship between obesity and type 2 diabetes mellitus (T2DM) is inevitable. The increase in the occurrence of obesity all around the globe has proportionally increased the occurrence of comorbidities. Periodontitis is a multifactorial inflammation of the periodontium attributed to dysbiosis in the subgingival microflora which may ultimately result in tooth loss. A triad between T2DM, periodontitis, and obesity is ascertained. Aim The present study focuses on investigating the association of obesity and T2DM with periodontal health. Methodology This cross-sectional study was conducted for a period of six months (September 2022 to February 2023) on 181 subjects, as per the sample size calculated by the statistician, who were previously diagnosed with T2DM and were either obese or overweight. The glycemic control was assessed on the basis of HbA1c values of the subjects. The subjects underwent bioelectrical impedance analysis along with an anthropometric examination. Full mouth examination including bleeding on probing, pocket probing depth, clinical attachment level (CAL), and oral hygiene index-simplified (OHI-S) was also checked to assess the status of periodontal health, and periodontitis was classified according to the new classification of 2017. Results The obtained data was statistically analyzed and p-value≤0.05 was considered statistically significant. The maximum prevalence of Stage III Grade C Periodontitis (34.73%) was observed in the diabetic obese group than in the diabetic overweight group. The overall anthropometric variable, abdominal circumference, waist-hip ratio, and basal metabolic index (BMI) were higher in the obese group as they displayed poor glycemic control. BMI and CAL also showed a positive correlation. Conclusion A significant association between obesity and T2DM with periodontitis was confirmed by this study. Hence, a syndemic approach needs to be formulated by the medical fraternity in collaboration with dental surgeons for the effective management of this triad.