I watch this game every few months with friends for laughs. I think that the development of the game was fairly casual and carefree as evidenced by the fact that one of the actors messed up a line and you hear everyone laughing about it.
My favorite sequence in the game occurs early on if you select the choice that has John and Jane wait to meet each other another time. They think to themselves that the other is not interested since the meeting didn't happen, and then create a long imagine spot in which they become completely different people altogether.