Of course. Imagine TellDear is successful and a lot of people use it to assess information pieces before consuming them, or to accompany them when reading texts or listening to podcasts, it would be in the interest of those who act in bad faith (because their goal is to persuade you or sell you shit) to score as good as possible. So they try to game the system by adjusting their creation.
Usually you want to make systems robust against being gamed. Interestingly, in our case TellDear explicitly encourages gaming. Please, go ahead and make your text better. Steelman your arguments, reduce rhetoric, remove propaganda, get your logic straight, make the facts you pick to prove your point less arbitrary. Great. If TellDear “approves” of your piece, you may actually have created something relevant although your intentions were very different.
This only works if TellDear does a good job. Gaming will also find bugs in TellDear , that’s for sure. Just let an AI text generator loose, check results, have it improve the text, and repeat until TellDear says “good job”. Then one of the following two is true: the text is good now or TellDear has failed – which it will often enough.