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Watchful vs Vigilant vs Wide-awake vs Alert

Watchful, vigilantwide-awakealert are comparable when they mean on the lookout especially for danger or for opportunities.

Watchful is the general word.

Vigilant implies keen, courageous, often wary, watchfulness.

Wide-awake stresses keen awareness, more often of opportunities and relevant developments than of dangers.

Alert stresses readiness or promptness in apprehending and meeting a danger, an opportunity, or an emergency.