Before we begin
Before we get into that, you should know that there are two types of milestones in a bear's storyline:
- Story Quests (where you talk to a bear and receive a task, do the task, and then report back to the bear)
- Story Chats (where you pass the milestone simply by having a particular conversation with a bear—no tasks involved)
I mention that because storyline milestones are given in a sequential, non-random way, but you might not realize this if you're only considering Story Quests and not Story Chats. (The Story Quests are generally obvious to players because of the untimed task involved; however, players might not realize they've had a Story Chat versus a normal conversation.)
So when do I get new Story Milestones?
In the vast majority of cases it boils down to, "If I complete a particular bear's milestone (Story Chat or Story Quest), then after N calendar days (not campaign days) that particular bear will give me its next milestone," where N is independently defined for each milestone of each bear. So if you wait for say 3 calendar days between play sessions, then you'll have a new milestone from every bear whose next milestone's N was 0-3 and didn't already have a milestone in progress.
In a small fraction of cases there are additional requirements besides waiting a certain number of calendar days. One example is Ranger Bear's 18th milestone. Ranger Bear is going to ask for something from another bear. Ranger Bear won't initiate that Story Quest until you get a certain ways into the other bear's story because we don't want players freaking out over an item they may not get for a very long time. I think this is an exhaustive list of such cases as of version 5.2.0:
- Ranger Bear's 2nd, 3rd, 4th, and 18th milestones
- Maker Bear's 2nd, 3rd, and 9th milestones
- Seagull Bear's 3rd, 4th, 9th, and 23rd milestones
- Wooden Bear's 4th milestone
- Scaredy Bear's 18th milestone
So what is N for each milestone of each bear?
It's beyond the scope of this article to tell you each number for each milestone. The smallest is 0 and the biggest is 12, and you won't encounter the largest numbers until you're quite far into the game. If you think you've been waiting too long for your next milestone and suspect a bug then consider sharing a photo/screenshot of your Progress Debug Screen with the folks in the Cozy Grove Discord. The friendly folks there may be able to help you figure out whether there's a bug or if the game is behaving as expected.