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Entertaining
8 Best Drinks to Order on a First Date

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In general, you should order whatever cocktail you damn well please—with one major exception: the first date. Don’t be the presumptuous guy who ordered not one, but two gigantic cocktails for himself when I said I only had time for one quick drink. Don’t be the pretentious guy who pulled an Alex Trebek, dramatically pronouncing Vieux Carre in perfect French. Don’t be the creepy guy who asked the bartender for a Sloe Comfortable Screw while maintaining eye contact with me. And definitely don’t be the guy who asked to trade cocktails with me because he didn’t like his order (“But you’re a cocktail writer, you like everything!”)

On a first date, you’re putting every aspect of yourself forward for judgement, and that includes your drink order. Your drink should give a first impression that speaks to your personality without speaking for it. So put your best foot forward with these foolproof drink orders, and save your secret Sex on the Beach jones for the third date.

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The Negroni is simple enough to not seem showy or awkwardly stump your bartender, yet still lets on you know a thing or two about cocktails. Its unassuming size won’t seem obnoxious, and you don’t have to worry about it spilling on your outfit like an unruly cocktail glass might. The Negroni is effortlessly cool and always sexy—hopefully your date will think the same of you.

The Essentials

Gin
Campari
Sweet Vermouth
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While it doesn’t get much better than a well-made Margarita, some people associate the drink with their wilder nights, and may think it’s inappropriate for a low-key date—especially if you’re at a place that will serve it in an oversized glass. Opt for another simple tequila cocktail, the Paloma. The mixture of fizzy grapefruit soda, reposado tequila and lime juice tastes just as refreshing as a Margarita but appears slightly more refined. Plus, you don’t have to risk embarrassing or treacherous glassware—the Paloma is typically served as a highball.

The Essentials

Tequila
Lime Juice
Grapefruit Soda
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If you’re craving bubbly, ordering a French 75 is the best way to subtly order Champagne without actually saying the word “Champagne,” which has the tendency to make dates roll their eyes at your Wolf of Wall Street money-throwing extravagances. Plus, it has gin in it, so it’s better than plain wine anyway.

The Essentials

Gin
lemon juice
Champagne
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If your first date is taking place over lunch, this low-ABV sipper is a great option for easy day drinking, and it looks more interesting than the standard Mimosa or pedestrian glass of wine. The Aperol Spritz is also an excellent late night choice for keeping your head clear. Ya know...just in case.

The Essentials

Aperol
Prosecco
Soda
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Maybe you truly love Gin and Tonics, but if you order one, your date is going to think you haven’t deviated from your go-to bar order since college. Instead of waxing poetic on how misunderstood tonic water is, just order a gin-based Gimlet instead and show off how mature you are.

The Essentials

Gin
Simple Syrup
Lime Juice
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There’s nothing wrong with ordering a Martini, but there’s a chance your date will think you’re a James Bond or Don Draper wannabe. Instead, try a sweet, sultry Manhattan. This classic whiskey and sweet vermouth cocktail is edgier than the Martini but just as iconic, and it oozes a dapper Old Hollywood vibe.

The Essentials

Whiskey
Sweet Vermouth
bitters
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We’re in full support of drinking colorful, fruity and, dare we say, stereotypically “girly” drinks—no matter your gender. That said, not everyone thinks that way. So instead of a Cosmo or Appletini, order an Aviation—an underrated sour cocktail that’s an alluring shade of violet, rather than neon pink. We guarantee your date will be intrigued and ask to sample a sip.

The Essentials

Gin
Crème de Violette
Maraschino
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When in doubt, you can’t go wrong with an Old Fashioned. Worst case scenario: You’re labeled a traditionalist (but the kind that likes cocktails). Best case: You’re a low-maintenance, sturdy and reliable person (but the kind that likes cocktails). Just be sure to stick to only one of these on a first date—this mixerless cocktail packs a punch.

The Essentials

Whiskey
bitters
sugar cube

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