A single gif could've turned the relationship from platonic to romantic
Background
We had a false start a while ago, and it feels as though there might be a chance he wants to date but is afraid to take the risk.
Goal
To date this man.
Conversation
Relationship Coach's Analysis
He initiated the discussion about dating you. So even though you replied with "why we lookin any further", he may still think you're joking with him (depends on how sarcastic you guys are together). Your last gif could've dropped a better hint that you were being pretty serious.