Osteoarthritis (OA) is one of the most prevalent degenerative joint diseases, which results in the inevitable destruction of joints leading to pain and joint immobility. Some studies have reported a potential link between diabetes mellitus (DM) and the worsening symptoms and severity of OA. Based on our literature review, the microcellular environment of patients with DM showed accelerated joint destruction and increased inflammation in every anatomical aspect of the joint including the bones, tendons, ligaments, cartilage, and synovium. Additionally, the biomechanical and biochemical properties of these tissues were more severely impacted in patients with DM and OA compared to those without DM, suggesting that DM plays an important role in the pathogenesis of OA. Specifically, we found that advanced glycation end products (AGEs) are the key to inducing the acceleration of joint destruction; however, their role in the pathogenesis has yet to be fully mapped out. In this narrative review, we aim to explore the role that DM plays in the acceleration of OA leading to increased reports of joint pain in those with both diseases. We believe this topic of discussion to be important due to the increased prevalence of both diseases over the last several decades, potentially leading to an increased medical burden on both patients and the community at large.