Content aware advertising isn’t the problem or even remotely as creepy.

If I’m reading an article about ski resorts it’s not out of line to try to sell me skis or even a vacation package. It pertains to the content thats being interacted with and may be a commonality across everyone interacting with that content.

If I then read a political news site and see the same ad it’s creepy.

The real world analogy is a guy literally following you around, seeing what storefronts you’ve peeked into, then holding up signs for them (or likely their competitors) everywhere else you go.