What you mention is the ability for your email client to send a "that email was read" message when you send an email with such a request.
This is why people build features like this. They want to track their email to you, and they want to do it without your consent.
It makes the whole interaction more creepy, moreover, I don't think that a lot of webclient support it (or even Smartphone apps).
It's kind of a dying feature.
I never considered that a consensual request prompt could be considered 'more creepy' than non-consensual spying. What about that interaction upsets you? Simply knowing that someone wanted to do it?
The reason people are creeped out when you ask them whether or not you can monitor them is because they don't want to be monitored. Skipping that question and tracking them without their permission doesn't make it less creepy, it makes it more creepy.