Complete Act 1

Take down Maurice

Arrive at Snowdin.

Get three items.

Get two items.

Enter the Ruins.

Scare the cat hiding from a party

Defeat N. Brio

Push 50 enemies with the Jelly Maker roar

Shut N. Brio up

Obtain all other trophies.

Complete The Stanley Parable in under 4 minutes 22 seconds (not including load times)

Quit the game and then start it again.