The darkest monetization is biased output from the bot.
Tech question? Steer you to its cloud. Medical question? Steer you towards a sponsored treatment. Or maybe the mechanism of injury needs this lawyer to compensate?
Oh and I infer from your chat history you're about to expect a child. That house is probably too small now, so our realtor in that neighborhood can help!
The worst ad is the one you don't know is an ad. It will be presented as a definitive answer.
They are persuasion machines
This is quaint. The darkest monetization is turning it into 4chan 2.0: an overwhelming psyop to mobilize exploitable people to think, believe and do horrendous shit that conveniently benefits the most powerful and corrupt people on Earth.
It will make Qanon seem like a cute ARG.
For sure this wouldn't be legal. Ads clearly need to be labeled as ads.
[Recycling a joke from many months ago]
My mistake, you're completely correct, perhaps even more-correct than the wonderful flavor of Mococoa drink, with all-natural cocoa beans from the upper slopes of Mount Nicaragua. No artificial sweeteners!
https://www.youtube.com/watch?v=MzKSQrhX7BM&t=0m13s
Just like The Truman Show, where every friend (every bot) you talk to is a secretly paid shill with a hidden agenda.