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So, you’ve finally nabbed a date with that sexy someone and you’re heading out to meet up for a drink. Your hair game is strong, you’re wearing your best duds, and you’re ready to impress with your most charming anecdotes and eye contact. But then your anxiety gets the best of you: what the hell are you going to order? A Shirley Temple with vodka, anything blue with an umbrella, Keystone Light, and anything with an unclever sexual name are all third-date drinks, for once your date already knows and kinda likes you enough to ignore what you’re drinking and focus on just having fun. And once you’re second guessing your libation of choice and dawdling over the menu, the confidence train starts chugging out of the station, leaving you awkward and hesitant. Don’t be that guy, guys and ladies! Here are 5 foolproof date drinks guaranteed to impress the object of your affection / attraction / infatuation, get you buzzed, and keep you calm:


The drink of James Bond and Dorothy Parker alike, this is a classic cocktail that impresses women with its sophistication and men with its straight-up attitude. Your chosen garnishes (olive? lemon twist?) and level of dirtiness may or may not display your hidden depths. Mmm, mysterious.

Bourbon on the rocks

This is one tasty brown liquor if you do it right, Basil Hayden’s, Knob Creek, and Bulleit are all smooth and pleasant enough to sip straight (or with a splash of seltzer if you’re a cheap date like me) over a long pleasantly rambling chat. If your date’s a whiskey connoisseur they’ll respect your fine taste. If they’re not, you can offer them a taste and impress them with yours. Just make sure to enjoy it slowly so you don’t look like a stiff-drink-swilling lush.

Good Beer

If you prefer pints over drams, a nice craft beer strikes the right balance between making you seem like someone who likes to have a good time but still has a decent palate. Operative word here is good beer. No Anheuser-Busch brews unless you’re at a dive bar or frat party, Choose something crafty or local. Don’t be annoying about describing the craftiness in a snobby way, though. Nobody likes a condescending hipster. Some widely available, super tasty, and ultra-dateable beers are Lagunitas Sumpin Sumpin, Brooklyn Lager, New Belgium Fat Tire, or anything Dogfish Head, though your mileage may vary. (If it’s winter — like it seemingly will be in the Northeast forever until we all die — look for a nice chocolatey porter or creamy vanilla-y stout)


An unfussy dark red wine that pairs well with most foods, this varietal (called Syrah or Shiraz depending on where the wine is made, though it’s the same kind of grape) is bold without being overwhelming, just like you should be on a date. (Hey-o!) Bonus: it’s good for your heart, so even if the date’s a dud, your drink’ll have your back.


If you simply must have your booze sweet, please for the love of all that is good and holy, choose this refreshing combo of mint, lime, white rum, simple syrup and seltzer over the saccharine sweetness of a frozen margarita or some insipid faux-fruit concoction, In the winter this may be hard to come by but most bars should be able to rustle up a modified version minus the mint. If you feel too prissy asking for it off-menu or you don’t trust the bar’s stock, a bottled (of if you’re lucky, draught) hard cider should hit the same note of refreshing sweetness without making you look like you’ve just turned 21 and are constantly trying to mask the flavor of your “yucky” booze.

Whichever type of drink wets your whistle, order with confidence, don’t get sloppy, and the rest of your date should be smooth sailing. That is, unless your date’s a total lunatic/bore/creep/mouth-breather. But you’re on your own with that one, buddy – I mean, go get ‘em, tiger!