So I just finished Dear Esteban.
The jam page for Dear Esteban sums up the point of the game nicely:
The engrossing world of “Dear Esteban” was created for a very simple purpose. To blow an existential hole in the players perception of their own realities. We wanted present a story so enriching to the human condition, that years from the initial play through the player will look back and think: “How was I ever that naive child before Dear Esteban pulled the wool off my eyes”. We’ve created an interactive tour de force, so powerful, that society at large will have no choice but to acknowledge video games as mankind ultimate art form and the final stage before the event horizon of the human singularity.
However, I think Dear Esteban is a brilliant example of how Dear Esther works from a design standpoint. As you probably know, the narrative of Dear Esther is delivered in slivers and fragments–it is never the same twice, and the seemingly random splicing of three “tracks” allows for contradictory information to be communicated to the player. This necessitates a mythmaking by the player. Each player becomes her own kind of weaver, making sense of what is being told to her in bits and fragments. She fills in the gaps with her own information. In this way, the interaction of a standard game (“press E to pick up random object”) is replaced with a purely mental interaction–we’re building the game’s narrative for it.
Dear Esteban takes this design mechanic and stretches it to the very limit. It tells us about people living in bars, cats, one-star reviews, and motorcycles suspended over heads. But it gives us no way to connect those things in time and space. But, as one of the developers said, “nobody has picked up on the deep hidden connection between all the narrative in Dear Esteban. Let’s get a flame war going for what the game…really means.” Of course, that doesn’t mean there is a connection; in fact, it is probably the best assertion that there is no connection between any of the narrative elements whatsoever.
But that doesn’t keep the player from trying to connect all of these elements. By stretching the symbolic/narrative participation factor to its very limit, we are able to see how sense-making is a part of all ludic events.
Look, all I am saying is that Dear Esteban is basically the broken hammer.