Scenario
Lia is the mother of a 4-year-old boy named Charles, and she is hoping to find a babysitter so that she can go on a date with her husband sometime this weekend. She already has a list of preferred babysitters, two of which she would be perfectly happy leaving Charles with. The third babysitter is perfectly capable, but not preferable because she is less active and engaging with Charles.
Lia starts by contacting her first babysitter, Ben. She tries to reach him on the phone, but he's in classes most of the day and so the phone goes to voicemail. Instead of leaving a voicemail and waiting for him to call back, she sends him an email. She asks if he is free on Friday night, since that is the night she was hoping to be able to have her date.
Ben receives the email, but has already scheduled a babysitting job for Friday night. Now Lia has to decide if she should contact the next babysitter, who might also end up being busy on Friday night, or continue trying to schedule with Ben. Lia sends an email to Ben asking about Saturday, and at the same time sends an email to her second choice babysitter, Hannah. The next morning, Hannah writes back saying that she is free on Friday night, and after negotiating the time in a few more emails, they agree for Hannah to watch Charles on Friday.
Design Sketches
Liz Simon
Design 1: A week by week calendar where you can click and drag to create events. Overlapping events might be shown in a few different ways: (1) decreasing the width to fit them side by side and cutting off the information. (2) Decreasing the width and color-coding with a key on the side or (3) Combining them into one item with all possibile babysitters/families listed. 
Design 2: A small screen interface. Only one day can be viewed at a time.
Design 3: A full month calendar view. A large span of dates can be seen at once, but not all information will be visible without clicking. In the babysitter view, there would be a green dot on each day that the babysitter is marked as free. Similarly, the parent view would have a dot on each day they posted a job.
