Eat where the booze is already picked out for you
Asking what to pair with your meal sucks: it can be embarrassing on a date, force an extended convo with a sommelier, or -- when he repeatedly suggests sex on the beach all googly-eyed -- both. So just avoid it all by hitting Leek American Bistro, where each dish has suggested drink pairings listed on the menu
From two local restaurant vets with over 20 years of experience, the Ballston corner spot's wedding invitation would read "tablecloth-casual". Lined with floor-to-ceiling windows and set off with bar built from stone and Virginian barnwood (oh you better believe it's reclaimed!), it pairs every one of its hearty American entrees with a beer, wine, and cocktail, with standout groupings including
Low Country Shrimp & Grits: Tasso ham, local cherry tomatoes, and white cheddar apparently go well with Murphy-Goode Pinot Grigio, Guinness Draught, or Bulleit Bourbon (maybe because the shrimp means you're already dealing with shell casings?)
Kansas City Strip: Dripping with peppercorn demi-glaze and sided by roasted garlic-smashed red potatoes & grilled asparagus, they recommend washing this steak down with Pilsner Urquell, the sweet basil, tequila Sweet San Antone, or 2005 Cab Sauv from B Side -- quite hard to track down
Seared Duck Breast: With a tea-poached pear and pickled daikon salad, the ginger-sake glazed bird goes down smooth with Brooklyn Brown Ale, Patron Añejo, or an '07 red zinfandel from Toad Hollow, which the creepy sommelier would suggest is a wild ride while caressing your date's arm.