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A Cynic's Guide to Date Nights For Every Bump in the Road

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Human beings enjoy a bewildering variety of pastimes. How are you supposed to guess if your date would like to be asked to the museum or the bowling alley, to go on a romantic adventure or just Netflix and chill? Food is the great equalizer because everybody gotta eat. Plus, dining out is a socially acceptable way to flex the plumage of your taste and the liquidity of your capital—and to have awkwardness-diffusing drinks in an environment that's not expressly about getting drunk. Still, there's a fine art to choosing the right restaurant for the moment. Follow this guide and you'll be dinner dating like a pro in no time, if by "pro" you mean a single thirty-eight-year-old. (You probably don't.)

FIRST DATE: OK, you only get one shot at this. Resist the temptation to go too fance or too low-key. You want to shoot the gap between trying too hard and DGAF. Besides, a three-hour feast at Death & Taxes is going to be excruciating if it goes poorly, while an empanada plate at Luna is going to zip by too fast if it goes well. For somewhere impressive that doesn't feel like you're trying to impress, try Counting House, but not the dining room. The bar has all the art-hotel chitchat fodder—hey, is that a chicken wearing a rabbit fur coat over there?—but with smaller, cheaper plates and cozy couches where curious knees can graze each other as you lean over a dish of oily olives. (And psst—if Date One was preceded by a Date Zero, like you randomly made out at an Arcana dance party or something, then you can probably skip this step and go straight to Date Three.)

THIRD DATE: Let's not be coy. It's 2018, and we've all been to this rodeo before. Three dates in, you are—how to put this delicately? You are open to certain possibilities. It's entirely possible that events will arrange themselves in such a way that you'll wish you hadn't had all those raw onions or black beans or spicy curries. By date three, you and your date tacitly agree you're worth splurging somewhere too expensive to go on the regs. Something light, luscious, and a little sexy, maybe. How about oysters at Saint James Seafood?

TENTH DATE: Figure one or two dates a week and you've been hanging out with this person for a couple of months. Things are starting to accelerate and take shape. By now, you've had a particularly good date somewhere, and the memory is taking on the first tint of nostalgia. It's time to go back there. This is going to be "your place." If you're lucky, it'll be somewhere like Garland, with consistent, inventive, James Beard Award-nominated fare that won't break the bank.

FIFTIETH DATE: A couple of months have somehow unspooled into a couple of years. Actual dates are coming slower. You keep talking about trying that hot new place, but the rez is a pain. After half an hour of listless deliberation, shrug and head to Spotted Dog for the millionth time, where everyone can get that perfectly good thing they always get and eat in patchy silence muffled by cheery eighties music and cute dog pictures. Oh, it's crowded? There's always Jade Palace take-out.

LAST DATE: Whether you're calling it quits or popping the question, you're going to want to put on a clean shirt for this one. Why waste it? Familiar enough for consolation yet special enough for proposals, Lantern will do fine in either life-changing scenario. The dark back bar hides tears of sorrow or joy equally well, and the adjacent patio makes for a quick escape into the rest of your life, whether it's back to Date Zero or whatever comes next.

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