A Gentleman’s Guide: Choosing the Right Wine for the Second Date

Shawn Zylberberg
5 min readSep 11, 2019

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Congratulations. You made it by a hair’s breadth. She likes you enough to tell her friends she went on a date with someone who didn’t wear a Blackstone vest or have white claw breath. Fall is around the corner and the leaves aren’t the only ones praying for a cozy landing in love. But the stakes are higher now, the competition fiercer, and the wine choices tougher to crack. You’re out to lunch if you don’t think her friends stalked your insta, looking for red flags such as a caption ending in “ — for the boys” or broken smiles. Her best friend already gave her 83 reasons not to date you, hell, she probably made a damn pie chart with your only hope being the tiny sliver that says, “If you were 38, then yes, I would accept him.” Doubt is the beast with no regard for love, so buckle up, throw out the mango claws, and show her you’ve been sent to Earth by Cupid himself because he was too busy playing archery with Chazz Michael Michaels. Your arrow is wine, use it wisely.

I. Whites

Sauvignon Blanc (Marlborough, New Zealand) $

Sancerre can smell what the ‘borough is cookin’ down under, and it’s quite richer. New Zealand whites have flooded the market in recent years with its explosive flavors. Savory notes of passionfruit, white peach, and green apple give this wine a fun, candy-like feel with a zesty finish that won’t spoil your palate or your wallet. If she likes light wines with big personalities, go with the NZ SB and pair it with brie or goat cheese.

New Zealand Sauvignon Blanc has gained popularity in the U.S. in recent years

Vermintino — Orange Wine (California, Oregon, Italy) $$

It’s pure disco inferno. This funky white pours a foggy orange hue that looks like a burning sunset in a sandstorm. It’s light, tangy, and a bit sour. One could call it a more complex sauv blanc, with a touch of grapefruit and a creamy minerality. It’s the cousin mom and dad told you not to hang out with on Friday nights. If she’s got the disco fever and no regard for predictable men, be a hero and get Vermintino. Pair with ricotta, pecorino, feta, or goat cheese.

Moscato $

It’s really fucking sweet.

Chablis (Burgundy, France) $$

A dry, acidic Chardonnay without the buttery coat? Shut up and take my money. This shit is good. White flower aromas with a tight minerality that accentuates a quiet citrus and pear flavor that opens up beautifully. Chill this baby and buy an extra bottle…for the third date.

Pinot Grigio (Italy) $

Super light and minerally, this white usually gets a bad rap. Some wine snobs “mistake” it for water, but it’s popular and girls love it, so who cares? Just do me a favor and go with the Santa Margherita if you feelin’ bad.

Champagne Papi cools off with a glass of Santa Margherita

Dom Pérignon (Champagne, France) $$$$

Is daddy’s AMEX glistening under the dim lights? Listen to the devil on your shoulder if the menu has the 2008 vintage. It’s exceptional and the name gives enough of a boost already. If the date takes a turn for the worse, order an emergency DP and watch how the candle starts to melt a little faster…

II. Reds

Syrah aka Shiraz (Côtes du Rhône, France or Australia) $$

If you chose Tempranillo (Spanish grape from Rioja region) on the first date, give this bad boy a try. Deeply complex and powerful, this dark-skinned grape is spicy. It’s famous black pepper bite reminds me of Sunday morning regrets that age into stories that belong in golden frames. It’s got class, but would also slap you hard enough to release the aftershave from your pores if cockiness got the best of you. If she asks for coffee at any point in the night, throw it in the damn trash because this blend of olive, herb, and pepper smoke will do the trick.

Tony Soprano enjoys Ruffino Chianti

Nebbiolo (Piedmont, Italy) $

One of Italy’s most underrated grapes, this red is bone-dry and generally light. Its leathery finish makes every sip feel brand new. Chill this red in the fridge while you guys spend 30 minutes in a pointless search on Netflix. It’s an affordable, entry-level wine that’ll make her forget she has a phone in her lap.

Petite Syrah (Napa Valley, CA or France) $$

You could stare at this wine longer than Bernini’s sculptures. The deep, purple hue is unmistakable as it quietly sleeps like a stingray on the ocean floor. It’s full like a cab, without its pretentious bite. She’s the quiet woman in a red dress, who rejects your cigarette offer because it would just fog up her view of the moon. On top of its beauty, it’s a rare variety with high levels of antioxidants and hints of blueberry, chocolate, and plums. In 50 years, she may set sail, never to return. So fuck it. Get a bottle and dance to Carlos Gardel as the world burns. (Hint: Zinfandel is a good sub)

Uco Valley, Mendoza

Malbec (Mendoza, Argentina) $$

Two names you need to know: Zuccardi and Catena Zapata. Both are family-owned wineries grown in the foothills of the Andes mountains, making for a powerful, full-bodied red with dark fruits like black cherry and blackberry. Bring a le labo candle to this date, because this red is meant to drink slowly, as every second that passes allows the flavor to reveal its secrets. Pairs well with any meats.

Brunello di Montalcino (Tuscany) $$$

Why don’t you hit me over the head with a shovel while you’re at it? Jesus Christ. She’s the most beautiful woman in all of Italy. The “Nessun Dorma” of wines. Let her decant for at least 30 minutes and she’ll tell you when she’s ready to swim in your glass. This is the wine that stops time for me. It carries bold flavors of wild strawberry, dried cranberry, and earthy espresso that, combined with its high acidity, make for a captivating experience. It’s made from 100% Sangiovese grapes on the sizzling slopes of Montalcino. Honestly, you might as well pack clothes for tomorrow because you ain’t going home tonight.

There are many wine experts out there who can point you to the back door to Rapunzel’s castle, but the choice belongs to you. Go with your gut and good luck. Remember, it’s just fucking wine.

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