The aim of this study was to evaluate the ability of Google Assistant, Alexa, and Siri to recognize and answer questions about male sexual health. Each VA was tested on a smart speaker: Alexa on Amazon Echo Dot 4th Gen., Google Assistant on Google Home Mini, and Siri on Apple HomePod. A pool of patients' frequently asked questions regarding erectile dysfunction (ED), premature ejaculation (PE), Peyronie's disease (PD), male infertility, and other aspects of male sexual health were identified by authors. The recognition of question was evaluated ("yes" or "not"). For each recognized question, the response characteristics (domains) were rated on a scale from 0 to 10 (according to the quality). We chose the recognition rate of the questions as the primary outcome and the quality of the answers as the secondary outcome. Overall, the best VA in recognizing questions was Siri, with a total of 83.3% questions compared with 64.0% for Alexa (p = 0.024) and 74.0% for Google Assistant (p = 0.061). Siri was associated with a significantly higher recognition rate than Alexa for PE (80% vs. 40%; p = 0.002) and PD (66.7% vs. 33.3%; p = 0.010). The quality of the responses was classified as low in 57 out of 105 cases (54.3%), intermediate in 46 cases (43.8%), and high in only 2 cases (1.9%), highlighting an overall intermediate-low quality of the answers. Male infertility was the condition associated with the highest mean scores in "Targeted response to the problem" (7.32 ± 2.57), "Scientific correctness of the answer", (5.9 ± 2.76) "Completeness of the answer" (5.14 ± 2.56), and "Understandability of the response for a patient" (5.3 ± 2.51) domains. Siri was associated with significantly higher scores than Alexa (p < 0.05) in several domains of all conditions evaluated. The question recognition rate of VAs is quite high; however, the quality of the answers is still intermediate-low. Siri seems superior to Alexa in both question recognition and response quality. Male infertility appears to be the sexual dysfunction best addressed by VAs.