Siri is the worst with this, but instead of "cutesy", when it's failing to execute a simple command, it goes for a smarmy and sarcastic response. I'll never understand the mindset of the putative audience who its designers think this will please.
Siri used to randomly give cutesy responses when I asked it to set a timer instead of repeating the time back to me, which I found incredibly annoying. Fortunately they stopped doing that a couple years ago.
Apple has definitely softened up Siri’s demeanor over the years, and I think it was a deliberate decision to introduce her as standoffish.
I once read that waitresses who initially come off as rude earn higher tips, but only if their mood softens throughout the meal. There seems to be something about “winning” the waitstaff over that makes diners reward them with higher tips.
IMO, it was a feature to have Siri come off as rude when her abilities and comprehension were still in development.
If asked the answer to zero divided by zero, she used to say a whole paragraph joke about how you’re sharing your zero cookies with zero friends because you have no friends. There’s videos on YouTube; I thought it was funny. They changed that a few months ago to something more “tame”, but still millennial/zoomer humor.
Today, in response to the query, "What is zero divided by zero?", Siri still gives a flip explanation (but now omitting the reference to Sesame Street intellectual property), followed by the one word sentence "No.". And that's when it's working as intended. Astounding.