So I was playing Dream the other day and I very quickly thought that the game was very pretentious. Which made me think about what it is to be pretentious and when it applies.
According to Google: "Attempting to impress by affecting greater importance or merit than is actually possessed."
Which sounds exactly what I was feeling.
This, I think, comes down to a very basic thing in storytelling: Show, Don't Tell (be careful with tvTropes.org by the way, it's a very big time-sink)
In a game that includes a narrator (like this one), it's a very easy trap to fall in to. It's much easier to make the narrator say: "Wow, that was cool!" than to make something actually cool. It's not nearly as easy to impress the player, after all.
On the other hand, if the narrator reflects what the player is feeling (especially after a beat pause), it can reinforce the feelings in a very positive manner. As the player then connects more closely to the character in the game.
A funny example that happened to me was in Just Cause 3, where I (kind of accidentally) drove a car off a cliff, jumping out of it at the last moment and hearing it explode below me. The character I was controlling spoke: "Perfect parking space." in a semi-proud, somewhat sarcastic tone of voice.
It worked well in the situation, increasing my enjoyment rather than making it feel awkward. And, fortunately, the game doesn't use this sound-bite too often.
Some people want to make a game that's thought-provoking and deep. And some games manage this without having to say that they are. The Stanley Parable and the rather oddly named Dr. Langeskov, The Tiger, and The Terribly Cursed Emerald: A Whirlwind Heist do a fantastic job of making the player think about their actions.
And exploration story-telling games like Gone Home can be incredibly good at making the player experience a whole range of thoughts and emotions. And they do it without telling you to feel a specific way.
So for me, something is pretentious if I feel that the message implies greatness that isn't present in the carrier. And by that measure, Dream most certaintly is... pretentious.
Anyway, just a random thought...