When phones' personal assistants (every company seems to want to have theirs these days) become orders of magnitude more advanced, we may be able to tell them to "check on our vacation booking" and they will know to search through our emails and calendars and connect the dots, so in those tasks they will be more advanced. There will probably be more services tied more deeply into them- for example, you'll be able to say "get me an Uber" and they will reply with "A blue civic will be here in 3 minutes", or "fill up the fridge on Sunday morning" and an Instacart-like company will show up at your door Sunday morning with eggs, vegetables (but no milk because you didn't finish this week's).

However, we won't be able to have those deep meaningful conversations with our voice assistants, because they won't have the necessary life experience to follow meaningful conversations. The current products on the market have no parents, no age, no experiences in school, no previous job, no former lovers, etc (they will jump around those questions playfully, but the canned answers get old quite fast). Those trite details that we recount when we bond with people do not exist in current personal assistants and likely never will.

There are several reasons for this: the first being that being able to model a structure of "life experiences" that can be queried based on what the user is saying is an incredibly complex problem on which we have pretty much no angle of attack on.

12 year old child: "I got picked on at school today."
Digital personal assistant: "You know, it happened to me too when I was your age. Let's talk to your mom about it."

Or even more complex:

24 year old student: "Hey, remember that problem on the Trigonometry 402 final from my senior year that I asked you to solve the equations for back in college?"
Digital assistant: "Oh yes! Here it is."

This, happening for millions and millions of possible interactions, life experiences, contexts? That's the algorithmic equivalent of light speed travel. Who knows maybe we'll get here one day. But 10 years from now? 50 years from now? 100 years from now? Not a chance. Remember that 40 years ago, Minsky thought it'd take a bunch of grad students a summer to write a program that recognize objects in pictures.

The second reason that such systems are extremely unlikely to emerge is that even if it would be doable technically, it would be extremely expensive to a company. And there would be literally no demand for it, because the overwhelming majority of people don't care about talking to robots. They already don't have enough time to spend with their children, partners, friends, parents... why would anyone waste time with a fake person? No company would invest the billions, if not hundreds of billions of dollars, to solve this problem in the next few hundred years.

Those questions of sentience and whether powering off a digital voice is "killing it" are appealing to ask to those of us who grew up reading Isaac Asimov, because we want this future to exist so bad. But they are red herrings- those questions have no meaningful answers, because our society is not configured in a way in which those questions could actually arise. When you turn your phone off today, the personal assistant definitely doesn't "die"; and in 50 years, even if it can carry out tasks way more efficiently and give somewhat more "human sounding" answers to certain categories of questions, people will still have no problem turning it off.