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I love it so far but I can't seem to get past the first day. Apparently Laguna is supposed to message you but I've tried a bunch of times, read all the forum pages, restarted, even tried on a different machine altogether and Laguna never messages me. Am I missing something?

Oh, what are the last messages you saw before the game stops sending messages?

I can make it through Sam's, purple squirrel, and andy's messages completely. They all log off and after that I don't get anymore messages. 

Specifically Andy's messages are about going to the basketball game and to make the 5pm reminder, same with Sam about going to the movie and putting that reminder in, and then purple squirrel having to go to dinner. 

I'm having the same issue sadly :( The last person I spoke with before reaching this barrier was Andy, I held off on starting the conversation with him until after I had spoken with Sam and prplsqrl. After he marked Away there was no other apparent way to progress.

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Ah, curiously, I restarted the game and something very different happened compared to when I was originally playing; originally, prplsqrl's spot on the Millenium Net Chat didn't even exist at all until AFTER I had found the private message on the PGFH forums and clicked the "add friend" button. With this restarted version, their icon and chat (plus pings) were viewable from the get-go. Whereas before I basically had no idea they were a part of the game until I found that private message. Might be a totally unrelated issue? But also hope this helps in some way, haha.

That was the same for me, but I had found the private message my first try at the game and was able to add them as a friend, but Laguna still never messaged me :( I’m wondering if completely scrubbing the game from my computer and redownloading might help, but I’m not sure where the game stores it’s other data. When I delete the game folder and redownload it everything I did (adding prplsqrl, all the reminders etc) persist.

That's really strange, it sounds like your game saved despite the fact it isn't supposed to be able to do so until you hit 'logout' at the end of a day's content :O That might be an additional issue too!

I finally found the issue! Picking options against going to the game with Andy made Laguna message me : D