Does it say somewhere that this tool is for a "first date"?

This is actually a great question. Some similar questions I have asked my partners:

* Tell me a secret

* Tell me your most embarrassing moment

* Tell me something bad about you

I remember a girl answering "my mother is crazy" to the first question.

The point of those questions are to deeply open yourself to the other. Share intimate moments. Create complicity. And in OP's tool it will also be about having an emotional roller-coaster (since it mixes happy questions with sad questions). Which as I've heard is the best way to get to someone's heart (debatable).