Get him to share his feelings
EJ is a very reserved person and sharing his feelings is not a comfort point for him unless you're super duper close with him. This is a very awkward topic for him if he's not used to you and questions revolving around this will often push him away.
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50 Ways To Annoy Eyeless Jack
RandomThese are a little more random than the last, but here are 50 ways to annoy my fandomized, let me repeat, FANDOMized perception of the Creepypasta, Eyeless Jack! Current Completion: 30 / 50