Society is ageing and the higher number of senior citizens in the total population is a challenge for society and often perceived as a burden. Negative images of old age can lead to ageism and poorer healthcare for older people. The younger generation will have to master these demographic challenges. Therefore, their attitude towards and their perception of the older generation has to be monitored. The aim of this study is to present the images of ageing held by dental students who received education in gerodontology and to assess possible changes between different generations of students over time and separated by gender. An annual, anonymous questionnaire survey was conducted among dental students at the end of the 10th semester each year between 2008 and 2021. The questionnaire surveyed personal attitudes towards ageing, the assessment of seniors, and personal experience with seniors (images of ageing, “Aging Semantic Differential”). In addition to confirming Friedan’s phenomenon regarding the assessment of age limits, the present study was able to demonstrate a positive image of ageing in dental students, which has remained almost constant over the years. An education in gerodontology might positively influence student perceptions of age and aging.