Our study aimed to explore how perceived baseline contact may influence acceptability of Connecting Today, a personal contact intervention, among people living with dementia. We aimed to generate hypotheses for testing in future studies. This was a sub-group analysis of pilot study data. Fifteen people living with mild to moderate dementia participated in Connecting Today. We explored how perceptions of intervention acceptability may differ in groups reporting weekly contact (n = 8) compared with groups reporting monthly/unknown (n = 7) contact at baseline. Measures of acceptability included a treatment perceptions and preferences questionnaire, and the number of and reasons for non-consent, missing data, and study withdrawal. We used descriptive statistics and content analysis. In visits one and two, a larger proportion (85.7–100%) of low baseline contact participants reported feeling better, and indicated that the visits helped them and were easy “mostly” or “a lot”, compared with the high baseline contact group (37.5–62.5%). Most missing data (71%) and all study withdrawals occurred in the high baseline contact group. Scheduled in-person visits with family, friends, or a volunteer may appeal to residents in care homes who have few existing opportunities for routine, one-on-one visits with others. Hypotheses generated should be tested in future studies.