The list, with notes.

Citywide

Dates Without a Drink

12 places

At some point "let's grab a drink" stops being a plan and starts being a reflex. Maybe one of you doesn't drink, maybe it's Dry July, maybe you just want to remember the date in the morning. These twelve places give you somewhere to sit, something to do, and no bar tab — a sober bar, tea rooms, board games, bookstores, and ice cream. Good for a first date, a fourth date, or a Tuesday when you'd rather not.

Citywide

Dates for a Heat Wave

6 places · Jul 2026

Some dates are ruined by weather and some are rescued by it. In July the whole city is outside, sweating through a rooftop reservation, pretending the view is worth it. These six rooms are cold, dark, and worth the trip — an oyster bar, a cinema, a library, a bathhouse, a marble house on Fifth, and a tiki bar with no windows. Good for a second date, an anniversary, or a Thursday when it is 96 degrees and you would like to be somewhere else.

Citywide

Order the Weird One

5 places · Jun 2026

Every cocktail list has one drink that sounds like a dare — mushrooms in the margarita, tomatoes where the gin should be. At most bars you order around it. At these five you order it, because the weird one is the best thing on the menu, and the hardware backs you up: North America's No. 1 bar, its No. 2, and Time Out's pick for best in the city are all on this list. The dare does half the work of the date.

Citywide

Chic Hotel Bars for a Date

6 places · Jun 2026

A hotel bar is the right call when you want the date to feel handled without announcing that you made a plan. The room does some of the work. Good lighting, real drinks, better chairs than your apartment. These six work for a second date, an anniversary, or a Tuesday when you want the night to feel like more than a Tuesday.

Citywide

Wine Bars for a First Date

5 places · May 2026

A wine bar is the right call for a first date for one reason: it lets you stay or leave. Two glasses and you're out in ninety minutes. A bottle and a cheese plate and suddenly it's last call. The room makes the decision for you. These five all do the job — small enough to feel chosen, good enough that you'll want to come back, and forgiving enough that you can talk for three hours and nobody will look at the table.