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In your comments you mentioned iCal, which has such functionality: if you have added your friend's calendar (be it Google or iCal like here), then you can just click Check Availability when you create a new event. Just add invitees and click on Check Availability button: which will open a nice time picker:


How many and which calendars should I use In my experience as few as possible. At first I liked the idea to have a calendar for each category (mine being "study", "personal", "important") and have a quick overview over my tasks. But when I wanted to sync my calendars to different devices it was sometimes a pain to set up all the different calendars. I ...

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