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We have a soft spot for grilled cheese, especially when someone gets a little ambitious with it. At Dear Irene in downtown Bend, that means Sparrow Bakery sourdough, melted raclette, a fried egg, and fig and thyme jam. That salty, sweet combination has plenty of appeal before you even get to the egg yolk. This is a sandwich worth sitting down for, preferably with enough time to order a few more things.

Dear Irene makes that last part awfully tempting. Pork and shrimp dumplings, seared scallops, and cocktails with pineapple and mezcal all compete for attention, while the dining room gives you velvet booths and a gold-accented bar to enjoy them in. The restaurant sits on Brooks Street near Drake Park, an easy detour from a downtown stroll. It’s also strictly for guests 21 and older, so save this one for a grown-up evening out.

Let’s start with that grilled cheese

Raclette brings the rich, savory flavor and generous melt that make a grilled cheese so satisfying. Fig and thyme jam adds sweetness and a little herbal flavor against the tang of the sourdough. Then there’s the fried egg on top, which makes a knife and fork a sensible idea. At $19, this is a treat-yourself sandwich, the kind we’d order for dinner without a second thought.

The sandwich has changed over time, as plenty of dishes do here. An earlier preparation used Taleggio, duck egg, and black truffle honey, so the kitchen’s fondness for cheese, eggs, and something sweet goes back a while. The raclette version keeps that appealing combination but takes it in a different direction. It gives us a very good reason to leave room for a sandwich even when seafood is calling.

There’s room to follow your appetite here. You can keep dinner relatively simple with grilled cheese and a drink, or build an evening around several dishes. There’s no fixed tasting menu to commit to and no reason everyone has to order the same number of courses. For a couple who can never agree on whether dinner should be snacks or a full meal, that freedom is welcome.

Dumplings and tostadas make sharing tempting

The pork and shrimp dumplings belong high on the list for anyone who loves a little heat with dinner. Black vinegar and chili crisp bring a sharp, spicy edge, with hoisin and sesame rounding things out. It’s an appealing change of pace alongside the richness of the grilled cheese. Order both for the table and you’ve already given everyone something very different to reach for.

The ahi tuna tostada goes another direction, with morita aioli, tomatillo salsa, and radish. Smoky chile and bright salsa are good company for tuna, and the tostada adds the crunch. It’s the sort of combination that makes a smaller plate sound more appealing than a conventional entrée. Sharing is an option, of course, but we understand wanting your own.

Beef and lamb meatballs with harissa, feta, and mint offer something heartier, while the shawarma-spiced pork ribs bring another set of warm spices to the table. There’s a lot to choose from without the list becoming enormous. Our approach would be to pick one rich dish, one with some brightness or heat, and leave a little room to reconsider. The dumplings are $21 and the tostada is $25, so several smaller plates can add up to a substantial dinner in both food and price.

Scallops or a whole roasted fish

Seafood gets plenty of attention in Jonny Becklund’s kitchen. The scallops come with red coconut curry, vegetables, and mushrooms, a combination with more warmth and richness than a simple squeeze of lemon. At $48, they sit toward the splurge end of the menu. For someone who plans a night out around the seafood, though, they’re an obvious contender.

Then there’s the whole roasted branzino, served with fennel, charred lemon, and piquillo pepper chimichurri. A whole fish makes dinner feel a little more leisurely, especially if you enjoy working through it between bites of the accompaniments. It’s $50 and offered in limited quantities, so ask about availability before settling on it. The kitchen’s seafood enthusiasm also runs through earlier dishes, including crudo and salmon tartare.

Chicken Milanese gives the meat eaters another reason to pay attention, with burrata and nduja puttanesca alongside the chicken. That’s a generous amount of richness and spice for a familiar dinner favorite. The $35 price also puts it below the seafood entrées. Between that, the grilled cheese, and the larger fish dishes, there are several ways to order without everyone making the same splurge.

A dining room with plenty of personality

The room deserves some attention of its own. Yellow and green stools line the illuminated bar, gold lights hang overhead, and patterned flooring carries the color through the space. Exposed brick gives all that polish a warmer backdrop. It’s a cheerful, richly decorated room, with enough detail to reward a good look around between courses.

Farther back, velvet seating and bold wallpaper give the lounge a more tucked-away feel. A booth would be our pick for a long dinner with someone we haven’t caught up with in a while. The bar has its own appeal for two people ordering drinks and a couple of plates. Either way, this is a place to make an evening of dinner.

It’s quite a transformation for the former Wall Street Bar space. Jonny and his wife, Irene, opened Dear Irene in July 2023 and named it after her. The personal touch suits a restaurant with such a particular look. You get the sense that someone enjoyed choosing these colors, right down to the upholstered seats and patterned walls.

The Oregon ingredients behind the cooking

Before Bend, Jonny was a chef and partner at Mr. Pollo in San Francisco, a small restaurant built around a changing tasting menu. He shopped at farmers markets and worked with what he found, rather than sticking to the same dishes every night. In Bend, the farmers market on Brooks Alley puts seasonal ingredients close at hand. The dishes change with them.

Sparrow Bakery, M’s Bakery, Carlton Farms, and Deschutes mushrooms are among the names that appear in the kitchen’s cooking. Those local and regional ingredients turn up alongside flavors drawn from much farther afield. Pork gets shawarma seasoning, and green beans get miso and yuzu kosho. For diners, that means familiar ingredients can arrive with a very different set of accompaniments.

Vegetables deserve a place in the order, too. Roasted carrots have appeared with labneh, nuts, and pomegranate molasses, giving the sweetness of the carrots something tangy and crunchy to play against. The polenta brings mushrooms, vegetables, and an egg together in a more substantial dish. At $28, it’s an appealing option when a warm bowl of something comforting sounds better than meat or fish.

Stay for a cocktail

With that bar running along the room, drinks feel like part of the occasion. The namesake Dear Irene cocktail combines vodka, olive brine, Lustau Blanc, and celery bitters. If a briny martini is usually your order, this is the one to consider. The Al Pastor Mezcalita takes a fruitier, spicier route with mezcal, tequila, pineapple, and lime.

Both cocktails are $17, and there are Oregon and international wines to choose from, too. Willamette Valley wines appear among the choices by the glass. There are alcohol-free options as well, including the NOgroni, Chill Pill, and nonalcoholic beers. You can enjoy the bar and the dinner without ordering alcohol.

Make an evening of it in downtown Bend

Dear Irene’s location makes it easy to add a little time outside before dinner. Drake Park is nearby, and Brooks Alley puts you close to downtown shops and other stops without needing to get back in the car. We’d leave enough time for a walk before the reservation. It’s a pleasant way to stretch a dinner date into more of an outing.

You’ll find Dear Irene at 926 NW Brooks Street in downtown Bend, near the entrance to Drake Park. A city-managed paid parking lot sits in front of the restaurant. Guests who need the accessible entrance should use 917 Wall Street and ring the buzzer for assistance.

This is a spot for guests 21 and older, and reservations are encouraged, though some seats are held for walk-ins. Groups of up to six can book online; larger parties should arrange their visit directly with the restaurant. Head to Dear Irene’s website for current hours, menus, and reservations.

If you have food allergies or dietary restrictions, check with the restaurant before booking. Most dishes cannot be modified, although gluten-free alternatives are available for some items. Menus and prices change with the seasons, and the photographs here include earlier preparations.

For a longer stay, our Bend restaurant guide has more ideas for breakfast, lunch, and dinner, including places to take the kids. For food stops elsewhere in the state, browse our Oregon Food and Drink guide. Keep Dear Irene on the list for an evening when you can take your time over a few plates and a good conversation.