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How to Make (and Order) the Perfect Second-Date Cocktail

Scotch & Soda? Nope.


Showing off is something of a lost art. Too often confused with peacocking or bragging (humble or otherwise), it’s been disdained and discouraged into near disuse. When it comes to dates, it seems the only acceptable form of showing off is planning a good one; anything showier and you inch dangerously close to hammy.

The thing is, when it’s done right, showing off conveys that you’re comfortable in your own skin and in your surroundings. It’s common wisdom that comfort and confidence are crucial factors of attraction, so you’re shooting yourself in the foot by shying away from a little showiness. The key, as with most things, is showing off subtly.

Let’s say this is your second outing together, and you’ve brought your date to the date-readiest speakeasy you know: sleeve-tatted bartenders, bare lightbulbs, all that stuff. It should be a favorite of yours, and it should be a bartender you know and trust; let your date in on your world a bit, signal your trust. But keep a few surprises in store. Say: “I’ve got this drink I think you’ll love” — something the bartender may not have even heard of, that you picked up somewhere. Walk your booze-smith through the steps, all Casino Royale-style, and let your date have the first sip. Relax and let your good taste speak for itself.

Are you showing off? You betcha. But note the difference between the man who says “I know this drink that you’re gonna love” and the one who’s all, “I know six bands you’ve never heard of.” One gives, the other hordes.

Of course, if you’ve found yourself a keeper, and you’ve invited said keeper over to your place for a drink, break out the shaker. When you’re a few dates in, you’ve got every right to go full-on Industrial Light & Magic. Just be sure you know a good drink before you start practicing your bottle flips.

Here’s one we learned from David Roth, a neighbor of ours at Cask Bar + Kitchen in Manhattan (incidentally a pretty decent date spot). Aromatic, smoky, and just sweet enough, the Mezcalero is inviting, but hints at an underlying depth. Feel free to take that as an example.

1 1/2 ounces Cointreau
1/2 ounce mezcal
1/2 ounce ginger syrup
3/4 ounce lemon juice
Grapefruit bitters
Grapefruit peel

Hawthorne strainer
Mesh strainer
Coupe glass
Atomizer (spray bottle)


1. Using the jigger, pour into the shaker Cointreau, mezcal, ginger syrup and lemon juice.

2. Add 2 dashes grapefruit bitters and fill shaker with ice. Shake.

3. Double strain mixture into coupe glass.

4. Peel a portion of grapefruit zest over the glass and squeeze. Wipe rim of glass with the inside of zest to release additional oils, then place in glass.

5. Using an atomizer, spray mezcal over the glass such that it mists the half-empty insides. Serve.

Recommended Mezcals: Montelobos Mezcal Joven; VIDA San Luis del Rio; Sombra

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