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Help?

Talk to him a lot, do favors for him, try to become his friend.
Eventually he will ask you about moving, just say yes and read what he replies.
If he replies that he actually doesn't want to move, turn your game off without saving and wait for him to talk about it again and reply that he will be moving out.
 
It takes time and depends. If you have a full town (10 villagers) every 2-3 days a villager should ping at you asking to move. But it doesn't cycle through everyone in town so sometimes a certain villager can ask multiple times before another one does even once. (I know this very well from having Freckles. You aren't leaving Felicity) But once they do ping you have the option to make them stay or go, but sometimes even if you say go they'll get upset cause you told them to leave. This is easily fixable if you just reset, go find them again and make sure they agree to leave. My recommendation if you want to get him to ping to move is seek him out at the beginning of your day or whenever you log on before you do anything that way if he does say no and you have to reset it won't take away anything you've done. Getting a villager to move takes patience. Freckles has been in my town for over 2 months. I want her to leave so bad. She's never pinged once.
 
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