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Capsules and coated pills are easier to swallow without water. But some pills will burn like crazy going down after you swallow them if you don't drink some liquid with them. Some also shouldn't be taken on an empty stomach.
the OP made me chuckle - the irresistible allure of the pointless challenge!
do note, though, that some tablets are supposed to be taken with a drink for 2 reasons; first, they can damage your oesphagus if they get stuck to the side on their way down, and second, they need a modicum of water to dissolve in once they hit your stomach.
It depends on the size, quantity, and desperation level.
I can swallow a few aspirin without water but there are giant horse pills out there (ie DayQuil gels) that I can barely choke down.
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