Credit: Andrea Bauer

Editor’s note: Chef Christian Gosselin left the restaurant in April 2013.

Popular oenology abounds with pro­fessional winos’ attempts to present the consumption of the grape as easy, affordable, and unintimidating. Over the years I’ve somehow managed to collect a small stack of books whose objective is to convince trembling neophytes that they’re smart enough and good enough to identify quality wine and procure it without the benefit of a trust fund or a Master Sommelier’s certificate.

Alpana Singh has probably done more to further those ends than anyone else in town. Still, she’s likely more recognized as the ultracongenial host of WTTW’s restaurant-review show Check, Please!—public television’s precursor to Yelp—than as the youngest woman to ever achieve the Master Sommelier’s certification, in 2003, or as the wine and spirits director for the Lettuce Entertain You empire. (She spent a stint in the lofty environs of LEY’s Everest in between.)

Her ten-season tenure on Channel 11 probably says as much about her quadruple-decker, wine-focused restaurant the Boarding House than any of her wine work does. During her run on Check, Please! (she announced her departure from the show last month), she never once betrayed a sniff of condescension among guests whose single commonality seemed to be that they existed well outside the jaded orbit of the food aesthete.

The Boarding House, for which she teamed with the owners of the tranquil Gold Coast French spot Bistronomic, presents that same sort of inclusiveness for wine drinkers. The space is comprised of a late-night basement bar that also houses the wine cellar, a rollicking ground-floor bar overshadowed by an extraordinary ceiling fixture built with nearly 10,000 inverted stem glasses (imagine God dumping an ocean of pinot noir on your head), and a third-floor main dining room with a mezzanine, a towering western-skyline view, and a discreet scattering of personal details, such as framed silhouettes of the proprietress turning up a glass or walking her pug.

It’s loud and it’s packed, especially in the bar, where one of the most age-diverse crowds in the city washes down unapologetically trashy bar food like pizza, poutine, and pork-stuffed tater tots to a soundtrack that veers from AC/DC and Def Leppard to Nicki Minaj and Rihanna.

The philosophical nucleus of this structure is a 30-page wine list with options at most price points, bottoming out at $38 and including many in the $40-$60 range. It’s a list that challenges you to know what you like, and I’m still not quite sure I’ve figured out the organizing principle. There is a bit of the yearbook to it, with sections separated with wine-related quotes by everyone from Hemingway to Larry David to Haruki Murakami. Old World wines are in the majority, classic grapes abound, and though it’s slight on Australians and South Africans, the west coast and South America make their mark. And there’s plenty to discover among, say, the selection of whites from Mediterranean islands, or an exotic such as a $120 red from Lebanon’s Bekaa Valley.

There’s something for nearly everyone, and it’s well worth giving it some study before you go, if only because your server has other tables to worry about. And if the search for the right bottle is too exhausting, there are 14 “top wines of the moment” and the same number of options by the glass.

In the context of this long and well-rounded list, Christian Gosselin’s accompanying menu is also manifold—and appears similarly designed to appeal to as many different appetites as possible. There is a lot on offer, but not much you haven’t seen elsewhere. In the bar you’ll find your cheese and charcuterie; pizzas, fries, and oysters; the aforementioned poutine; and beers and a few cocktails if you don’t feel so Dionysian.

Are they trying to tell us to get drunk? Gosselin, who came lately from the Sofitel’s Cafe des Architectes and Bistronomic, additionally offers a poutine pizza, and in the upstairs dining room there’s yet another version of the Canadian atrocity, this one with chunks of tender lobster that start to toughen from the radiant heat of the fries just as the cheese curds begin to congeal. Oh well. If Gosselin, a native Quebecois, can’t convince me that poutine isn’t a crime against frites, then I suppose no one can.

The lobster poutine illustrates the duality of a dining room menu that’s trying to include both the irreverence of the bar’s menu and a more straightforward, even conservative, meat-and-starch-entree approach. So upstairs you have snacky, drunky, deep-fried things—battered cauliflower nuggets with a trio of dipping sauces or hard-fried and regrettably underseasoned chicken with buttermilk biscuits—along with a series of incompatible and formulaic entrees characterized by flesh propped above pureed starch and drizzled with a thick, syrupy reduction.

It could be a stringy brick of short rib blanketed in crushed hazelnuts and paired with sweet potato puree or lukewarm slabs of red venison and poached persimmons resting in pureed parsnip—the effect is the same. You’re eating meat and potatoes (or something very close to it) and the more you eat the more difficult it’ll be to heave yourself out of your chair. Even when entrees forgo roots for another vegetable or a grain, it’s still a bloated, dull affair. From a poached and seared salmon fillet on polenta studded with whole black garlic cloves to gelid seared scallops atop cauliflower puree, one starts to sense that Gosselin is operating out of a slim playbook.

These larger plates don’t often approach the vibrancy of certain smaller ones, including a slippery linguine with spicy coins of linguica sausage, a geometrically perfect block of grass-fed steak tartare glazed with caper aioli, and a Serrano ham and braised radicchio salad mined with deposits of smoked ricotta cheese. Aside from these the menu is built from a formula that largely fails to match the sense of discovery that the wine list inspires.

Exceptions can also be found on the dessert menu, where pastry chef Julia Fitting presents over-the-top sweets like a sugar pie the density of a Chinese moon cake; an oatmeal cookie sandwich with a creamy maple-bourbon filling, half dipped in dark chocolate; or a chocolate-covered marshmallow bombe plated with the indulgent redundancies of a toasted marshmallow kebab and a cup of hot cocoa. Among the dessert wines there’s a creamy Uruguayan fortified wine that tastes of blackberries and chocolate that shouldn’t be missed with any one of these.

The Boarding House is, simply, a large-format wine bar on a grand scale. Singh’s populist approach to the wine—and the inclusive environment in which to drink it—comes across easy. Finding something good to eat with it is a little more intimidating.