Single-sided deafness (SSD) significantly restricts social participation in hearing/speaking cultures due to the person’s difficulty hearing conversations on their deaf side. Although hearing aids for SSD are effective in social situations, the acceptance rate remains low at 4%. To address this problem, we designed and developed a bone conduction-based device to be worn with eyeglasses, involving 53 individuals with SSD including two authors. We conducted a four-week diary study comparing our proposed device with traditional Contralateral Routing of Signals (CROS) hearing aids and explored the factors that might affect the acceptance rate of assistive devices for SSD. The findings indicated that our design was more acceptable for users with SSD due to its effectiveness, social acceptability, and the ability for wearers to use other devices simultaneously, such as earbuds. Based on our results, we discuss implications for designing wearable assistive devices to promote greater acceptance among the target population.