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A guide · Citywide

Order the Weird One

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.

Published June 2026

The weird drink has one job: start the conversation.

Every good cocktail list has one. Mushrooms where the lime should be, tomato where the gin should be, a sour named after a pastry. At most bars it's a trap. At a bar with hardware on the wall, it's the kitchen showing off — and the smartest thing you can order on a date.

Why the weird one works

Two people ordering negronis are having two separate drinks. Two people splitting something that sounds like a mistake are having an event.

The order is a move. It says you're game, it gives the night its first shared risk, and the first sip hands you a conversation neither of you has to manufacture. Best case, it's the drink you talk about for a week. Worst case, it's the story.

How to spot it

It is not the longest ingredient list. It's the one that sounds like an inside joke — one savory thing where sweet should be, one name that makes you read it twice.

If the bartender grins when you order it, you found it.

Order one, not two

Get one weird one and one safe one, then trade halfway.

If the weird one wins, the night has its headline. If it loses, nobody's stuck holding it — and you've learned something about each other's nerve either way.

Let the bartender talk

At bars this good, the bartender wants to tell you what huitlacoche is. Let them. Once.

Then turn back to your date. The drink is the opener, not the evening.

The rule

A drink that sounds like a mistake, at a bar that wins awards, isn't a mistake.

Order it. Hand it across. See what happens.

The list

  1. Superbueno

    East Village · $$$

    No. 2 in North America two years running, and the weird one is the Mushroom Margarita — mezcal, huitlacoche, somehow a love story. Neon, Lucha Libre murals, cumbia loud enough to lean in. The room flirts for you.

    13 1st Ave, New York, NY 10003

  2. Sip&Guzzle

    West Village · $$$

    North America's No. 1 bar, and the Tomato Tree has no business working — and does. Two rooms in one address, loose upstairs and hushed Ginza-style below, so the night can change registers without moving.

    29 Cornelia St, New York, NY 10014

  3. schmuck.

    East Village · $$$

    A living room from Barcelona's Two Schmucks crew, where the menu reads like a kitchen dare — Bread With Tomatoes, a caramel-apple milk punch. Walk-ins only, open till one, built for dates that refuse to end.

    97 1st Ave, New York, NY 10003

  4. Bar Snack

    East Village · $$

    Time Out's No. 1 bar in NYC with nothing over $18 — a Cannoli Sour, a thing called the Gordo Gordo, a Spice Bag to share. The lowest-stakes room on this list to test the thesis.

    92 2nd Ave, New York, NY 10003

  5. Dear Irving Gramercy

    Gramercy · $$

    The weird one here is the room: era-themed parlors from Marie Antoinette to JFK, with a button at the table that calls the next round. The drinks stay classic so the setting can be the experiment.

    55 Irving Pl, New York, NY 10003