First Stop: Drinks
I like drinking wine; I love tasting wine; I really love tasting wine with the intent to actually drink it. So I'd start off somewhere my date and I could share quite a few half- or quarter-glasses: the spiffy self-service Enomatic at SD26, maybe, or the amazing wine bar at Maialino (now, all Italian whites). For something a little more casual (particularly if we get an early start), maybe Brouwerij Lane in Greenpoint, where you can try all sorts of high-octane microbrews for a few bucks per sizable pour. Or, for something a little more sit-down date-y, I might stop by Akariba, the sake bar that's part of Zenkichi—pickled, aged fish innards are totally romantic, right?
Second Stop: Small Plates
I'm a nibbler at heart; I'd rather take one bite of six appetizers than have one to myself. So anywhere small plates-friendly would be a great next stop: tapas at Txikito, the killer veggie dishes (not the pizza) at Otto, or just about anything at Terroir. (And all these places are wine-friendly, too.)
... or not small plates?
Then again, I haven't stopped thinking about the cauliflower soup at Fedora in two weeks, and a seat at the bar, plus an Old Fashioned, would make a mighty fine second course, if it's cold out. So would the Hete Blicksem or Bitterballen at Vandaag. And Valentine, if you really want to charm me, here's a second-course gift idea: stracciatella from Eataly is the best cheese this girl's ever had.
Third Stop: Main Course
I don't mind if things get a little cheesy on Valentine's Day —I've done heart-shaped pizza at Motorino and fondue at The Bourgeois Pig in the past, and would happily do either again. If my dinner had been moving along in an Italian direction, I might stop by Convivio for just about any pasta on the menu. But the idea of non-stuffy steak also appeals, so steak frites at Le Relais de Venise L'Entrecote would fit the bill, too.
Fourth Stop: Dessert
If I could wriggle my way in, I'd just plop down at the bar at Locanda Verde and ask Karen DeMasco to bring us absolutely anything she wanted. But if that's not to be, I'll head for the ricotta fritters at Al di La in Brooklyn, a little closer to my own neighborhood; nothing in the world makes me as happy as fried dough. Or if we just wanted to head home, a pint of Bklyn Larder's fior di latte gelato. At $9, it's an occasion dessert, but worth every penny.
If there's a blizzard raging, or we're short on time, or my date isn't as excited about a five-stop evening as I am—though that's not going to happen, right, darling?—I would happily dedicate all my courses to Torrisi Italian Specialties or Zenkichi. Torrisi's changing menu and friendly, small dining room always feels like a special occasion; Zenkichi's curtained-off booths are made for date night. (Just don't go poking around the other tables.) Neither is cheap, but the prix-fixe takes some of the pressure off ordering and means you won't be surprised by the bill at the end.
Last Stop: After-Dinner Drinks
Given that my other half is as devoted to Ward III as I am, that's sure to be our last stop—but to mix things up beforehand, I'd love to try the Brown Butter Old Fashioned, or any of the other drinks, at the Gramercy Park Hotel. A hot, steaming mug of Ixcacao from Huckleberry Bar would put me right to sleep—but for a longer night, Mayahuel in the East Village would do nicely, amazing mezcal drinks and tucked-in booths, totally sexy but not overdone in the least. Exactly how I want Valentine's Day to be.