The relationship between subjective well-being (SWB) and frequent attendance is understudied. This study used data from a large German sample of non-institutionalized individuals aged 40+ in 2014 (n = 7264). SWB was measured using the Satisfaction with Life Scale (SWLS) and the Positive and Negative Affect Schedule (PANAS). Number of self-reported dental visits in the past twelve months was used to measure the utilization frequency of dental services. Individuals with at least four dental visits in the preceding year (highest decile) were defined as frequent dental visits. Robustness checks were performed using alternative cut-offs to define frequent dental visits. Multiple logistic regressions showed that frequent dental visits (highest decile) were associated with less satisfaction with life [OR: 0.89, 95%-CI: 0.80–0.99] and higher negative affect [OR: 1.41, 95%-CI: 1.22–1.64], whereas it was not significantly associated with positive affect. Both associations depended on the cut-off chosen to define frequent dental visits. The present study highlights the association between SWB (particularly negative affect and low life satisfaction) and frequent dental visits. Further studies evaluating patients’ motivation for high dental service use are necessary to check the robustness of our findings.