Hello hello! Sorry to hear you're having trouble! Here's a few things you can try to get back on his route when you're struggling!
-Meet with him in the cemetery
-Tell him Crowven is your cousin when you do!
-Tell Crowven you'll pick up something while you're out when you leave that one morning!
-Think about the married couple that came in to the diner when Mary is reminiscing
-Call Reginald in the diner!
Those choices together should get you back on Reginald's route. Hope that helps!!