Maggie Appleton thinks there should be Speculative Calendar Events.
I don’t want to add them as real events. Because they are not real events. They are speculative possibilities of events. The majority of them won’t be filled, and having both speculative and real events looking and behaving like the same type of thing is messy and confusing. I can’t glance at my calendar to get a quick read on how busy my day or week is.
Maggie was thinking mostly of those things where you offer someone a number of different calendar slots over email and they can pick from them (to be more accommodating), so you’d put all of them on your calendar, but only as possible events, not real ones.
Her starter idea:

I’d take it! I’m not as popular as Maggie, but sometimes that kind of calendar golf comes up for me too.
More often, I’m paging through the weekly local rag and see some concerts or other events I might want to go to. Just recently I wanted to put all the Suttle Lodge Fireside concerts on there just to remember, as I’d like to make one. I’m tempted to put them on the calendar, but my family dynamic is such that CALENDAR = TRUTH. So putting events on there is like: this thing is happening. If there were a kind of speculative event type that we all understood, that would be nice. (Maybe we should just use an entirely new calendar so it could be color coded, I dunno.)
I’ve settled on the “new color coded calendar” option myself. I have one called “Potential Concerts” for concerts coming up that maybe I’ll go to, maybe not, and if I decide to go to it then I’ll duplicate the event into my actual calendar. It’s not perfect, but it gets the job done.
I’ve done this for years, and indeed another calendar is the perfect way to do it. My colour for that colour is yellow, as in “caution.” It works great.
The new Hey.com calendar includes the “Maybe” events feature with a different presentation style. https://www.youtube.com/watch?v=SztU4232u_o&t=691s
Yeah Maggie mentioned that in her post as well:
Kinda feel that.
I’ve been super surprised how much outlook has been improving lately. It’s just been getting better usability and works cross platform pretty well. I’m even considering switching to it for my personal. I just use the tentative status in there for maybe meetings. I also pre-pend the meeting title with “Tentative:” or “Confirmed:” when setting options like research sessions. What I do wish is if people would spend more time managing their calendar and respect other folks time. How could a smarter calendar encourage better behavior?