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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:


I won't directly answer your question, but this may be helpful, and it's too much for a comment. What you describe is a standard "daily stand-up meeting". This is a canonical component of the Scrum software development framework, but it also makes sense in other contexts. Typically, such a "daily scrum" has three agenda points for each participant: What ...

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