The purpose of this study was to examine the association between sleep quality, frailty, and human relationships in Japanese older adults (aged 65 years and above, excluding those certified as requiring long-term care). This cross-sectional study used a questionnaire survey to gather demographic information, data on frequency of conversation and conversation partners, and employed the following validated instruments: Kihon Checklist (KCL), a Japanese instrument used to determine the care needs and frailty of older adults; the Dysphagia Risk Assessment for Community-Dwelling Elderly (DRACE) scale; Japanese versions of Pittsburgh Sleep Quality Index (PSQI-J); the Geriatric Depression Scale-15 (GDS-15-J); and the University of California Los Angeles Scale (UCLA-J), an instrument to assess loneliness in older adults. The 500 respondents were divided into two groups based on sleep quality (PSQI-J): low sleep quality group (n = 167, 33.4%) and high sleep quality group (n = 333, 66.6%). Our analyses showed that the low sleep quality group had a KCL score of 5.55 ± 2.47, which indicated frailty. Binomial logistic regression analysis identified age, number of diseases under treatment, DRACE, GDS-15-J, and conversation frequency and discussion partner for important matters as factors (p < 0.05) associated with poor sleep quality. These factors could help enhance the detection of frailty and predictability of caregiving needs.