Here are a few lessons I've drawn...
a. Obviously, try to avoid rain. If you decide on a rain date, specify exactly what constitutes "rain." E.g. "if the weather.yahoo.com forecast includes the word 'rain'" ... If you mean "rain or shine," SAY rain or shine.
b. graphic invitations are cool
c. an aural cue is better than a set time. You can tell people there will be a referee's whistle (and then be sure to bring one!), or set the event for when a certain clock chimes, if there is one.
d. encourage people not to be in the area at all until the very last minute. That's the beauty of a flash mob. Also, then no one will feel "gosh there aren't enough people, I'll go home," because no one knows how many people until too late. There were about 12 people in Dorchester Square until the very last minute. Then suddenly there were 50. Then 100.
e. a cutoff time is not a bad idea, so people don't come late. Ours lasted 30 minutes, but it was pretty much done after 15 minutes.
f. after work is a good time. Night is cool for a pillow fight but day provides better pictures.
g. do not wear your fragile #&*)&*)# plastic glasses! Unless you needed a new prescription anyway.
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Pillow fight!