Speech alignment is where talkers subconsciously adopt the speech and language patterns of their interlocutor. Nowadays, people of all ages are speaking with voice-activated, artificially-intelligent (voice-AI) digital assistants through phones or smart speakers. This study examines participants’ age (older adults, 53–81 years old vs. younger adults, 18–39 years old) and gender (female and male) on degree of speech alignment during shadowing of (female and male) human and voice-AI (Apple’s Siri) productions. Degree of alignment was assessed holistically via a perceptual ratings AXB task by a separate group of listeners. Results reveal that older and younger adults display distinct patterns of alignment based on humanness and gender of the human model talkers: older adults displayed greater alignment toward the female human and device voices, while younger adults aligned to a greater extent toward the male human voice. Additionally, there were other gender-mediated differences observed, all of which interacted with model talker category (voice-AI vs. human) or shadower age category (OA vs. YA). Taken together, these results suggest a complex interplay of social dynamics in alignment, which can inform models of speech production both in human-human and human-device interaction.