Based on a previous investigation, a quantitative study aimed to identify user’ preferences towards four synthetic voices of two different quality levels (classified through the sophistication of the synthesizer: low vs. high) is proposed. The voices administered to participants were developed considering two main aspects: the voice quality (high/low) and their gender (male/female). 182 unpaid participants were recruited for the study, divided in four groups according to their age, and therefore classified as adolescents, young adults, middle-aged, and seniors. To collect data regarding each voice, randomly audited by participants, the shortened version of the Virtual Agent Voice Acceptance Questionnaire (VAVAQ) was exploited. Outcomes of the previous study revealed that the voices of high quality, regardless of their gender, received a higher acclaim by all participants examined rather than the corresponding two voices assessed as lower quality. Conversely, findings of the current study suggest that the four new groups of participants involved agreed in showing their strong preference towards the high-quality voice gendered as female compared to all the other considered voices. Regarding the two voices gendered as male, the high-quality one was considered as more original and capable to arouse positive emotional states than the low-quality one. Moreover, the high-quality male voice was judged as more natural than the female low-quality one. Results provide some insights for future directions in the user experience and design field.