I thought this was going be a clever algorithm, but after so many tries it felt like Tom Sawyer had tricked me into doing data entry for his AI.

I started thinking the same thing and started entering in a bunch of nonsense.

What was the result?

Think of a word related to both transsexual and potato.

Chaz?

We basically said the same thing at #4 (cloudy & cloud) which I thought was pretty damn impressive (we started with the robot saying "assuming" while I said "color") but then it took a lot of runaround (I wasn't sure if we could repeat words or not?) till we both said "freeze" at number 15.

Try #2:

1 fist hair
2 chin nail
3 fingernail body
4 scalp finger
5 forehead itch
6 pimple skin
7 acne zit
8 wrinkles pimple
9 scars skin
10 peel scab
11 scratch blood
12 bleeding cut
13 slashed hurt
14 stabbed knife
15 knives stab
16 daggers gun
17 weapon weapon

14 & 15 were so annoying, we basically just switched what we were saying. It gets to where you can't come up with a new way of saying the same thing, so I went a different direction, and said "gun" figuring I could bring it back out to a main category and we would both say "weapon" next. So, it worked, but only because I gamed it, you know?

Finally. I am done now.

Round Me You
1 residence robot
2 mansion house
3 townhouse home
4 apartment apartment