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watchful is the general word implying a being observant and prepared, as to ward off danger or seize an opportunity under the watchful eye of her guardian; vigilant implies an active, keen watchfulness and connotes the immediate necessity for this a vigilant sentry; alert implies a quick intelligence and a readiness to take prompt action alert to the danger that confronted them; wide-awake more often implies an alertness to opportunities than to dangers and connotes an awareness of all the surrounding circumstances a wide-awake young salesman
See watchful in Webster's New World Roget's A-Z Thesaurus II
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