Yay! We have our own discussion thread; how fun.

Hooray for you! It sounds like you’ve made a lot of progress. Okay, so…
1) I have no idea, honestly. If you do have to raise friendship with the guy, then I’d assume that the only way to do that is to talk to him.
2) Uhhh I’m not sure about this one either :’) She should come along eventually. Perhaps you should keep the trumpet out on the shelf? Maybe her arrival at the village is determined by story progression rather than selling X number of items? It seemed like she came somewhat later in the game.
3) Haha, this is just a test of your patience :> I read somewhere on GameFAQs or some other place that there’s a 25(? Might’ve been less than that)% chance per day that the desired fruit will show up. I almost restarted my most recent file because I’d played for days on end and couldn’t get the fruit that I needed. Some files I would find the fruit pretty quickly, but other times it would take me forever to find the fruit. Hang in there, and try to be patient! You’ve got this :D
4) uHhhHhhHh….HOPEFULLY he will! This will probably be another test of your patience. Look out for it every day.
Hmm. I apologize for not being able to answer any of your questions with certainty. Kind of a random question, but where are you in the game? I mean, what’s happened? I’m curious because there are several different story arcs. I mean, have you triggered the events with Helena? Have you unlocked Harvey’s Secret Fort yet? I’m curious about that kind of stuff. :p
(I’ve been wanting to make some Hometown Story art and post it on my art thread, but I haven’t had the time to do so

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