Objectives The quality of sexual life of elderly people represents an understudied topic of sexual medicine and of psycho-sexology. Hence, we aimed to evaluate the association of specific psycho-relational variables, such as intimacy, increased affective gestures towards a partner (AGtP), daily shared activities, and dyadic satisfaction, with the psychosexual wellbeing of elderly people, expressed in terms of sexual satisfaction. Methods: A cohort of elderly people was selected from a sample of a broader study evaluating the role of sexual activity in protecting the emotional wellbeing of a population subjected to quarantine due to the COVID-19 pandemic. Specifically, the presence of sexual dysfunctions, the emotional wellbeing (i.e., absence of anxiety and/or depression), and the quality of the partners’ relationships were studied. For the study’s purpose, the Sexual Health Inventory for Males (SHIM), the Female Sexual Function Index (FSFI), the Orgasmometer and the Orgasmometer-F, the Generalized Anxiety Disorder scale (GAD-7), the Patient Health Questionnaire (PHQ-9), and the Dyadic Adjustment Scale were adopted. Results: A group of 124 elderly subjects (≥60) was selected for the study’s purposes. Among these, 84% were males (120/124), and 16% were females (20/124). All the subjects declared to be in a stable relationship and to be sexually active during the first lockdown period. Gender differences were found for the Dyadic Satisfaction subscale (males: 37.04 ± 6.57; females: 32.85 ± 10.04; p < 0.05) and the Orgasmometer (males: 7.64 ± 1.30; females: 6.60 ± 2.46; p < 0.01). Linear regression analysis showed the association between higher Orgasmometer scores and: (i) the absence of sexual dysfunctions (β = −1.213; SE = 0.271; p < 0.0001), (ii) higher dyadic satisfaction (β = 0.042; SE = 0.019; p < 0.05), and (iii) reduced shared activities with partner (β = −0.463; SE = 0.143; p < 0.01) and increased affective gestures towards partner (DAS measured AGtP) (β = 0.595; SE = 0.065; p < 0.0001). Post hoc analysis of ANCOVA with the Bonferroni correction method showed a significant difference in the Orgasmometer scores between subjects with and without sexual dysfunction (mean difference: 2.102; SE = 0.340; pBonf < 0.001), with healthy subjects reporting higher scores compared to dysfunctional ones. Conclusions: It is reasonable to suppose that, beyond the presence of sexual dysfunctions, the sexual health of elderly people may benefit from the quality of the relationship, and, specifically, from the presence of affective gestures towards the partner and the dyadic satisfaction. To the contrary, the quantity of time spent together, sharing specific activities, may be considered a factor worsening relational and sexual health. These data should be considered during the evaluation of sexual health among elderly people.