This study aims to compare rates of depressive and anxious symptoms among older adults with and without diabetes. The study also examines differences in depression, anxiety, and diabetes-related emotional distress between middle-aged and older adults with diabetes. A total of 224 participants completed a range of questionnaires measuring depression, anxiety, and diabetes-related emotional distress (if applicable). One hundred and three adults with diabetes (55 middle-aged, mean age = 47 years, range 40–59 years and 48 older, mean age = 69 years, range 60–81 years) were recruited from a tertiary diabetes clinic. One hundred and twenty-one adults without diabetes (72 middle-aged, mean age = 52 years, range 40–59 years and 49 older, mean age = 65 years, range 60–76 years) were recruited from either a university student pool or a registry of adults aged 50 and above. Older adults with diabetes had significantly higher levels of depression and comparable levels of anxiety with older adults without diabetes. Older adults with diabetes had significantly lower levels of depression, anxiety, and diabetes-related distress than middle-aged adults with diabetes. Diabetes is associated with high rates of depression and anxiety, with middle-aged adults more adversely affected than older adults.