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In order to get Dan to join the party, and unlock the Creep achievement, you must do activities in your apartment until you hear a knock at the door. When you do, go check the door.

If a creepy NPC pops into the view of the eyehole, and is named Creep, that is Dan. Say "Hello" to him, and then open the door. When he asks if he can hang out, choose "Come in", and he will join the party, unlocking the Creep achievement in the process!

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