Six stories about Alpana Singh

The Check, Please! host is opening her own restaurant. Is Chicago ready?

Photograph: Chris Strong
Alpana Singh

One

Alpana Singh is taking a photo of me with her husband, Charles Blackstone. I look like Blackstone, and I act like Blackstone, and he looks and acts like me. We’re at MingHin, in Chinatown. On this evening, Blackstone and I happen to be wearing similar shirts, making us look even more alike. The similarities are freakish. A few days earlier, Singh, 35, looked at me and said, “You look so much like Charles I want to tell you all my secrets.” (She didn’t.)

“This is insane,” Singh says as she takes the photo. Then she puts down her phone and, very seriously, starts ordering food.

“The pork belly,” she says to the server.

“The pork belly,” the server replies, writing it down.

“Stir-fried string beans,” Singh says.

“The string beans.”

“The crispy duck,” I say.

This gets no response from the server.

(“I want that, too!” Blackstone whispers to me. “We’re the same person!” I whisper back.)

“The beef ribs,” Singh says.

“The beef ribs.”

“The crispy duck,” says Blackstone.

The server shoots him an angry look. She starts walking away. Singh catches her.

“The crispy duck,” says Singh.

“Crispy duck,” the server says.

Two

Singh likes small, family-run restaurants like MingHin because her parents once ran an Indian grocery store in Monterey, California, and it, too, was a small, family-run place. In 1987, when she was 11 years old, Singh started to work at the store after school. In 1991, the store closed, and Singh got a job at Bakers Square, where her mother also worked. Her mother understood the concept of hospitality. “If you’re serving somebody ribs, and you know they’re going to get messy, why not give them extra napkins?” she’d say in what was a roundabout training for Singh. She picked up the concept of hospitality quickly. She was a straight-A student. She’s a quick study.

Singh appreciates luxury restaurants, too. When the tips at Bakers Square stopped cutting it (Singh wanted to go to UC Berkeley, and she knew her parents couldn’t afford it), she signed up for the Air Force. That didn’t work out. So she got a job serving at Montrio, a fine-dining restaurant in Monterey. Then things started happening fast. The restaurant won Esquire’s Best New Restaurant of the Year; Singh got a second job at a wine store and, after a couple of years, left Montrio to work in wine retail exclusively; she went to the Masters of Food and Wine event in Carmel, California, and flirtatiously sauntered up to a table full of French chefs (she wasn’t interested in them, but in their Riesling); one of the chefs was Jean Joho, who minutes later asked her to be the sommelier at Everest; Singh accepted and moved her life to Chicago; Singh took the master sommelier exam; she became the youngest woman in history to pass. This was 2003; Singh was 26.

Like I said, she’s a quick study.

Three

“Where are the maître d’s?” Singh cries at the end of our meal at MingHin. We are two very strong gin and tonics and an extra order of pork belly into the evening. “Where did they go? I’m bringing back the maître d’!”

Singh does not suffer from delusions of grandeur. At her new multilevel, multiconcept restaurant, the Boarding House (see “Facts about the Boarding House,” page 17), opening later this month in River North, she really is bringing back the maître d’. His name is Matthew. He’s in charge of the dining room, in charge of the servers, in charge of knowing the names of the people who expect their names to be known. And Singh is teaching him—and everyone on staff—what it means to be soigné: to provide elegant, seamless luxury.

“It’s in my orientation packet: ‘Soigné service,’ ” she tells me over white pinot noir (Singh’s pick) at RM. It’s just her and me, a week before we go to MingHin. “It’s something I learned from every French person I worked with: Make it soigné, make it soigné.”

I tell Singh I love this word, that it sounds like something out of an orientation packet RuPaul would write. In response, she kind of grunts in bliss: “Ugh!” She closes her eyes and waves her hand through the air like a delicate linen napkin. “Make it soigné.”

Four

People who watch Singh on Check, Please!, the WTTW program she has hosted since 2003, when she replaced Amanda Puck, might wonder just how involved she is in the Boarding House. I wondered that, too. Is she just the face of the operation, a celebrity attraction for restaurateurs Matt Fisher and John Ward (who also own Bistronomic) to use to get people in the door? In other words, is she just a younger, Indian, female version of Art Smith?

The answer is Singh won’t touch the music. “I have terrible music taste,” she says. “We’d have Dusty Springfield. It’d be Steely Dan all night long. I’m not allowed to go anywhere near the music.” Everything else is her.

One afternoon I watch her in the Boarding House’s test kitchen, in the abandoned LM Bistro space in Lincoln Square. The executive chef, Christian Gosselin, previously the chef de cuisine at Bistronomic, presents her with a vegetarian small plate: soft, spiced cauliflower fritters, almost like cauliflower pancakes. For Singh, they aren’t working.

“What if you kept the floret whole and dipped it in a batter?”

“Then I would have to do it maybe with a temp—”

“Tempura batter! So we spice the cauliflower…”

“You want to use the same spices?”

“Yes, absolutely, I don’t want to lose the spice. I’m thinking texture. I’m thinking crispy. So it would be kind of an Indian take on tempura. And who doesn’t love tempura?”

Gosselin doesn’t skip a beat.

“Everybody loves tempura.”

Five

An hour into our conversation at RM, Singh begins to cry. Singh is confident and collected and forward and tough, so this is a little startling.

We’re talking about her time at Lettuce Entertain You. I want to know two things: Why would a woman like Singh, who appeared to have a plum gig as Lettuce’s wine director, leave such an influential and lucrative (I assumed) position? And if a woman like Singh wanted, for whatever insane reason, to open a restaurant, why not do it with Lettuce, and all the resources, support, capital and safety that comes with it?

“I was in a very strange place last year,” she explains. “Without even knowing I was in a strange place. It was not until I left Lettuce that I realized how much of a strange of a place I was [in].”

Her trajectory at the company went like this: After five years at Everest, Singh ceased feeling challenged. And she was very open about it. So in 2005, Lettuce moved her to the corporate office, where the company created a role just for her (nobody held the wine director position at Lettuce before her, and nobody has taken it since she left). After six years of creating wine programs for places like Frankie’s Scaloppine and negotiating Lettuce’s huge alcohol accounts, Singh started feeling restless again. Working on Lettuce’s Wine Cellars, an online wine club, engaged her for a bit. But “I kept plugging away, plugging away, but it was kind of like, now what, now what, now what?”

She had a surprising realization. “Part of me was sort of, I wanna go back to the floor. I miss the floor. I miss interacting with people. I miss that instant gratification.”

She decided she wanted to get into the restaurant business again.

“Did you ask if you could do it with Lettuce?” I ask.

“No, I didn’t.”

“Did it cross your mind?”

“No, it didn’t. Which says a lot.”

“I wanted something all to myself,” she continues. “I wanted to be able to execute every single decision. I think that’s part of why I never approached them.” (Lettuce never approached Singh, either. President Rich Melman remembers his reaction to the news of Singh’s departure as supportive of her choice. “When you care about somebody—and I care about her—you want them to do what’s right for them.”)

In Fisher and Ward, Singh had found partners who would give her creative control. She tried to warn them. She told them she would want a lot, like temperature-controlled wine storage and health insurance for her servers. They agreed nonetheless. They trusted her. She could do what she wanted, which, she admits, is a scary place to be. “Let’s face it,” she says, “I’ve been on a show for ten years that reviews restaurants. And now that person who hosts the show about people criticizing food is about to open a restaurant? No pressure!” She’s doing it anyway, because she wants to “take the blame, take the fall, take the credit, take the joy and take the pain.” Just her. “I wanted to stand on my own.”

So last fall, when Fisher, whom Singh had befriended via many meals at his previous restaurants, Tallulah and Eve, showed her the space, a three-story former nightclub at 720 North Wells Street, she fell in love with it. But first, she had to talk to Melman and Lettuce CEO Kevin Brown.

This is the part of the story where Singh cries.

“It was one of the proudest moments of my life. I get teary just thinking about it.” She’s fanning at her eyes but it’s no use. The tears are here. “Kevin said to me: ‘You’re ready.’”

Six

Is Alpana Singh ready to open a restaurant in Chicago? Halfway into a glass of white pinot, she may express some doubts. When she’s tasting wine for the Boarding House, it’s a different Alpana.

We’re at the test kitchen, sitting with an importer and a distributor, who are trying to sell Singh their wines. When Singh finds a bottle she likes, she starts negotiating. “I want this,” she’ll say. And if the distributor doesn’t have enough, Singh lets out a high-pitched, comedic “Whaaaaaaaaaat?” And then everyone at the table laughs.

But now they’re talking about a Champagne from Singh’s past.

“I love that wine,” she says.

“We’ve got some, and it’s in stock and it’s wonderful.”

“It has that beautiful bottle. Oh, my God, that bottle is so beautiful. I used to pour that by the glass. How much did it jump up to?”

“It’s $850.”

Singh whips her entire body around. “Are you kidding me?”

“It’s a $1,700 case of wine.”

“You’re on crack,” she mutters, and passes on the Champagne. At this stage in the game, Singh isn’t shedding any tears.

Facts about the Boarding House

• The restaurant, slated to open later this month, is three concepts in one. First floor: casual wine bar with thoughtful bar food. Top floor: fine dining. Basement: a lounge.

• It has a 350-bottle wine list. That’s small for a sommelier like Singh, but she plans to constantly change it up.

• Tony Potempa, formerly of the Pump Room, is on cocktail duty. Expect lots of color.

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