Since Coffee Shop opened in 1989 on the north end of a then-ragtag Union Square, the area has changed a lot. But this chic, deco standby has retained all the charm it had in its heyday: The staff is still uniformly young, gorgeous and lithe (mostly models and aspiring actors who dish out what many rue as spotty service), and the hours are still convenient for both Bloody Mary-soaked brunches and perfectly tart, late-evening Caipiroskas. The swoopy, bustling bar up front is manned by young aloof bartenders who mix impressive dirty gin martinis ($10) and the like to an eclectic crowd of business types and downtowners sharing a quick nightcap. If it's too frantic for you, make your way into the dimly lit lounge in back. With a cozy fireplace and a bartender who is a little more inclined to chat up the crowd, this buzzes with hushed energy and feels like a secret.
29 Union Square W., (212) 243-7969. Veronica Cooper