I dated the woman who did the voice for Google Voice (the voicemail service). She moved out to CA with me when my company got accepted to YC and she got a job at Google. I dunno exactly how she ended up doing the voice for it, but it's always been vaguely surreal to hear her answering my phone (I use Google Voice, and last I listened she was still the voice ~9 years later). It's not that big of a deal, more of a weird anecdote (that I've very rarely had occasion to tell before now) than anything traumatic.

Seems like a personal assistant voice would be kinda the same. Though maybe you hear it more often. But, it's probably not something that happens very often. I mean, how many personal assistant voices are there, and how many people can they have dated?