This achievements is missable. You can earn this at the end of chapter 3 during your playthrough. If you miss it, the quickest way is to rewind to chapter 4 rather than playing through chapter 3 again.
Solution contains some spoilers.
*** Spoiler - click to reveal ***Towards the end of chapter 3 you will have to pick up 6 blocks of clay and go outside dressed as an Enderman to put them in a specific order. Going outside will trigger the end of chapter 3 and the start of chapter 4.
Normal Playthrough
Before you go outside, approach Reuben who is stood near the door. Press 
to go through the various conversation options available. After you have done them all, the will still be there to talk again. You will need to keep trying to talk approx. 10 times until Jesse says something along the lines of "I'd love to hear a joke". Wait for the conversation to be over and then the achievement will pop after that.
Rewinding to Chapter 4
You will start the chapter outside with a door behind you. You can walk back through that door which will lead you to the room with Reuben in where you can follow the steps above.