Fun idea, but the AI ruins it. Both from a perspective of "AI is a plague upon any creative works, and seeing it is repulsive"... but also from a perspective of "it just doesn't work".
Try this: What do you think this is? 
AI guesses: HANDLE, DOORKNOB, DOOR, BUTTON, SWITCH
Actual answer: KEY
What about this?
AI guesses: JOB, SPEECH, HABIT, OFFICE, SCHOOL
I doubt I even have to give the answer to this one.
The words are ridiculously imbalanced: 20 words is absurdly small for most of these, even if you could get them first try. Even WITHOUT the increasing constraints, this game seems like it would be very difficult and RNG-dependent.