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If you've already dropped multiple times, it should have been explained by now.
Watch the gauge by your health. When it empties, you drop. Various things can affect the speed at which it drops -- items like Drop-Me-Nots can make it drop much slower, while enemy attacks like Poison and Sleep can make it drop much faster.
"I once got a spam email entitled 'SIX STEPS TO A GREAT CAREER.' I was really disappointed when it wasn't an ad for revolvers." - todaystomsawyer
It's not random. with a 1x drop speed it takes 20 minutes between drops.
what a terrible game design...
Only if you're not managing the drop bar.
Basically learn to drop gauge, it's a very nice asset when you take full advantage and utilize it properly. It's actually very well designed to the point that if it's causing your problems well it's pretty much all your fault.
I've got a quote that embodies you perfectly, but it's seventy-three posts long, has a few massive flowcharts, and lots of Xion-KMA to Me