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Our philosophy is that, for every person, there is the right drink at the right time, and we strive to make your experience uniquely tailored to your palate. As you walk through our doors, it is our goal to make you feel at home and at ease. Daniel Shoemaker
You may not realize it, but every aspect of Daniel Shoemaker's popular cocktail lounge was carefully designed to make sure your afternoon or evening out is a singular experience—the subtleties are quietly celebrated in the details. The island bar was designed to allow you to comfortably communicate with companions three stools down or with new friends across the room. The street-side windows are opened when it's warm, linking the outdoors with the in. And then there are the drinks. Shoemaker estimates the lounge's cocktail Rolodex is comprised of nearly 400 original, classic and interpretative drinks (gleaned from friends in the industry) made with fresh fruits, (often) obscure ingredients, and handcrafted bitter tinctures that give the bartenders a lot of space in which to play. But don't let that intimidate you. Shoemaker's staff is there not just to serve you, but to understand what you like and learn what you may like. A good bartender, he says, is more than just the sum of knowledge and technique—he or she is, above all, a welcoming host.
Daniel Shoemaker's craft cocktail lounge has everything you want when it comes to getting a good drink: professional, but never stiff, bartenders; a chic, yet casual communal space; and a drink rolodex that includes more than 400 cocktail recipes. Much smaller is the lounge's food menu, but whatever's on it—it changes frequently—is made with as much care and foresight as your drinks are.
Forecast: There aren't a lot of seats here—four tables that seat about 20—so the best time to claim one is right at 4 p.m. when the doors open. Still, whenever the weather's nice, the lounge's windows are also opened, bringing some of the outside inside.
Advisory: You can bring your dogs, but you'll need to find a sitter for your kids (unless they're 21 or older).
SPF: There are no tree canopies or umbrellas to protect you from the summer sun, but that's nothing a cold one can't cure. And if you're lucky enough to have a seat when the sun sets over the western hills, you're in for a lazy, slow, colorful treat.
Barometer: Shoemaker suggests both Love in the Afternoon (rye and aprium—an apricot-plum hybrid—with lemon-basil soda) and, of course, the laboriously, yet lovingly crafted seasonal piña colada (aged Flor de Caña rum, cream of coconut, pineapple juice, pineapple gomme and lime juice in an umbrella-spiked Hurricane glass).
We've come to expect great things from the bartenders at Daniel Shoemaker's Teardrop Lounge. Since the doors opened, they've been mixing inventive and often surprising cocktails that are always artfully presented, whether the spirits are garnished with origami-like fruits or simply poured over rocks in a pretty glass. The drinks on the current happy hour menu are no exception. To get a taste of what they do best, try the nutty, tart and brilliantly pink Afternoon in Paris (gin, Lillet Blanc, pastis, lemon and Peychaud's bitters) or the impossibly chocolatey Graduate (sweet vermouth, tonic water and a jigger of orange curaçao that burnishes the drink's shot of blended Scotch). What you may not expect, however, is how good the food is. Teardrop has a tiny kitchen and, therefore, a limited menu, but you’d be cheating yourself if you pass on the kitchen's pork belly sandwich (served on a ciabatta roll with whole-grain mustard and a green cabbage and red onion slaw). For such a small kitchen, the pork belly's preparation is as complex as the drinks. First, the pork is brined for a full day. Then, it's cooked confit-style, after which it's pressed, portioned and floured before it's finally gently fried. Portland's seams are bursting with great sandwich carts and shops, but Teardrop's pork belly sandwich is among the best the city has to offer. Ask for one and see if it doesn't surprise you as much as the drink you're pairing it with. Happy hour runs from 4 to 7 p.m., Monday through Friday.
You're forgiven if you've never really considered the food at Teardrop Lounge. After all, you've bellied up for the drinks, not the eats. But, unless you're a vegan or vegetarian, that forgiveness is conditional and expires at the end of this sentence. The next time you're in the mood for a sandwich, head to Teardrop and ask for chef Mark Dunleavy's pork belly sandwich, a bread, meat and greens thing that's seemingly simple yet anything but. Depending on how it's prepared, pork belly, with its fat over fibrous tissue make up, can leave even committed carnivores feeling kind of squicky. But not this pork belly, because Dunleavy brines, stews, presses, portions, flours, and fries the pork before resting it, with some fresh slaw and whole-grain mustard, between two Pearl Bakery ciabatta roll halves. You might think that it's one of those rare sandwiches that inexplicably needs no cheese. But you'd be wrong because there's cheese in there, a housemade mascarpone which, along with the housemade mayonnaise, sweetly binds together the sandwich's green cabbage and red onion slaw. Even when they seem familiar, the drinks at Teardrop have always surprised you. Now, let the food.