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Perhaps this is a multipart question, but I deal with a lot of calendars in my life, and want to know if there is some way to sync them all together, and maintain appropriate privacy.

So I have a family calendar that my ex and I maintain for kid events, and I have a personal calendar for my own life, and I have an Outlook work calendar, for work. Ideally I'd look at my calendar on my Android phone.

Is it possible to sync them all together? Is it possible for there to be one calendar to rule them all on my phone, but have the other calendars blank out spaces that are from other calendars, but only show the blanked out without the details. (I don't want my date with Miss Hottie to appear that way on the family calendar, and I probably don't want my visit to the proctologist to appear in the corporate exchange server.)

Are there tools available to do this?

Bonus question, can I do the same with my to do lists?

Double bouns question -- how can I solve world hunger and help us to all live together in peace? :-)

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I've been looking into this. gSyncit and SyncMyCal seem to be the best options for syncing Outlook with multiple Google calendars; I've not yet tried either. I have multiple Google calendars and I sync one of them with my personal Outlook using Google Calendar sync, which only supports one Google calendar <-> one Outlook calendar. My work stays separate, it's behind a firewall etc (the Good app lets me see it on my Android).

Perhaps you should center on Google calendars--sync your work Outlook with the main Google calendar, create other calendars to manage your other stuff, then use gSyncit to keep it all together. gSyncit advertises it can selectively sync, for example your Miss Hottie appts, so that only free/busy shows instead of the details.

If your phone is Android you'll be able to see all of your Google calendars. I like the free Business Calendar for its ease in showing multiple calendars and selectively hiding them, and also free Jorte.

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Not sure if this does exactly what you want, but I've tried dozens of solutions and I like this one the best by far, though it's not perfect.

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