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This is extremely difficult to explain, so I’ve created a fiddle to help:
http://jsfiddle.net/csaltyj/VRZef/
Size the panes so that the first row of boxes goes from 0 to 10. Click on box 13. What I’d LIKE to have happen is have those four empty spaces to the left of box 13 be filled with 20, 21, 28, and 29. In other words, I want the boxes to wrap completely to the left and flow AROUND box 13. Is this doable?
Unfortunately this is not possible in pure (modern browser supported) CSS.
I would recommend checking out Masonry. It is a jQuery plugin that handles this in JavaScript.