In an aging society, improving quality of life for middle-aged and senior citizens is crucial. In Taiwan, karaoke recreation is a popular event among senior citizens. This study examined the effects of singing on middle-aged and senior citizens via testing such individuals before and after singing. The tested aspects consisted of social psychology, social interaction, emotional reaction, and usability. The experiment design categorized karaoke events into “group singing” and “individual singing.” The tested karaoke equipment consisted of conventional physical karaoke equipment (hereafter referred to as conventional karaoke equipment) and new karaoke software applications. Experiment participants comprised 48 middle-aged and senior citizens from Miaoli, Taiwan, who were divided into three groups, namely individual participant using digital application, individual participant using conventional karaoke equipment, and grouped participants using conventional karaoke equipment. Results revealed that after singing, the participants’ social avoidance and distress levels decreased, their emotions improved and strengthened, and, and they demonstrated enhanced social interaction behaviors. Furthermore, group singing yielded greater effects than individual singing did, whereas the effects were greater among participants who used conventional karaoke equipment than those who used digital applications. Participants who used conventional karaoke equipment demonstrated enhanced emotions, social interactions, and satisfaction with usability. Despite attempts to enhance competitiveness via integrating online social functions, new karaoke software still has space for improvement.