Family Tree

The Many Lives of Alpana Singh

From determined college dropout to Master Sommelier, television personality, and restaurant owner, Chicago’s celeb somm has done it all

Alpana Singh
Alpana Singh. Photo credit: Jeff Schear.

“Holy Alpana Singh!”

His eyes turned toward the heavens, his hands stretched out in mock supplication, culinary designer Tommy Walton is kvetching—loudly—on an episode of the WTTW Chicago restaurant-review television program “Check, Please!” Walton, a panelist, has just returned from a sketchy-looking hole-in-the-wall diner and is questioning Singh’s judgment in sending him to review a dive.

As Walton rants, the camera swings left and catches Alpana Singh, doyenne of fine dining and host of the program, momentarily losing her composure. First she covers her face with her hand as she giggles. Then, succumbing to the moment, she leans sideways, under the table, for a deep belly laugh. A moment later, the lens captures her again: She’s coughing, tears streaming from her eyes.

But then Singh is back on track, all business—looking straight at the camera and closing out the segment. She’s got this.

The episode, which originally aired eight years ago, may have been a star-making turn for Walton, who would go on to be a popular contestant on “MasterChef” with Gordon Ramsay. (“That scene was originally much funnier—they edited it out,” recalls Walton, chuckling. “Alpana spit out her whole mouthful of wine onto the floor.”)

But the real star of the segment is Alpana Singh, Master Sommelier, restaurateur, force of nature. On “Check, Please!”—which she hosted from 2003 to 2013—Singh has an engaging television presence: She exudes a coquettish warmth that visibly relaxes the show’s guest panelists, who are Chicago residents, not media pros. At the same time, she manages personalities, keeps her eye on the clock, and takes control of the room when she needs to.

“Chicago is a Midwestern city,” Walton observes. “There are a lot of tourists here coming to the ‘Big City’ for the first time. She’s one of the smartest people I know but at the same time very approachable, very likeable. She takes away that intimidation factor.”

A Natural Star

Singh is strikingly attractive, with a mischievous sparkle in her eye, and she is quick to see the humor in any situation. “She is a fabulous impersonator,” says Evan Goldstein, MS, the president and chief education officer at Full Circle Wine Solutions, a wine education and public relations firm. “She tells wonderful anecdotes and stories. She helps humanize this work for a lot of us. There are peers of ours who get a little too stuffy and hardwired. When she goes out as an emissary, she brings an accessibility to the court.”

The up-and-coming somms who have found their footing under Singh’s guidance repeat Goldstein’s sentiments: Singh is an engaging teacher thanks to her ability to bring lightness to any subject, her willingness to clown around, and her knack for compelling storytelling.

“She fostered a great sense of fun,” recalls Seth Wilson, currently the wine director at Booth One in Chicago. “Her educational style was one that everyone latched onto. She made wine sexy.” Wilson trained under Singh at The Boarding House, her handsome four-floor restaurant in Chicago’s River North neighborhood, between 2012 and 2015. “She told stories about her travels around the world,” he says. “She would hold up her leg and pretend it was a map of Italy and show you where things were located on her leg. I have taken that into my own wine direction: Using humor and storytelling as a way to teach and educate.”

“You know when Alpana is in the room because of this incredible booming laugh she has,” says Joe Spellman, MS, the national accounts manager at Justin Vineyards & Winery and Landmark Vineyards. “She’s gregarious, friendly, and positive. You know she is having a good time.”

In the late 1990s, Spellman was the sommelier at Charlie Trotter’s in Chicago, and he remembers having a conversation with Chef Jean Joho. “He said he didn’t need a sommelier,” Spellman recalls. “He knew wine. He could choose the wine himself.” Then, a few years later, at the glittering Masters of Food & Wine event in Carmel, the chef came across Singh and offered her a job on the spot. “He was smitten by her charm and social graces,” Spellman says. “The fact that he would hire a sommelier was surprising to me, but I suppose not to her.”

By the age of 23, Singh was running the wine program at Everest, Joho’s highly regarded fine-dining institution on the 40th floor of the Chicago Stock Exchange. Three years later, in 2003, she became the youngest woman ever to pass the Master Sommelier exam, the same year she landed the coveted hosting spot on “Check, Please!”

Enfant Terrible

The flip side of magnetic charm can be arrogance, and Singh is the first to admit that when she broke into the industry, she may have left some shards of glass on the floor. “She just had a way of connecting with people that was very socially and professionally advantageous [to her],” observed one well-known sommelier whom I contacted for this article. Another somm politely declined to comment.

“I was called an enfant terrible for a very long time,” Singh says. “I kind of had an attitude—you know, aggressiveness, defensiveness, a chip on my shoulder. I could run a wine program, I could blind-taste, I could pass the test—but I was still working on the person.”

Since those days, Singh, now 41, has lived through a lot: a divorce, a departure from her partnership in a 300-plus-seat restaurant venture—Seven Lions—after two and a half years, and a recent near run for political office. (After a successful fundraising campaign, Singh changed her mind about running for a position on the Cook County Board of Commissioners.)

“We strive for these awards, but we ignore the personal development,” says Singh. “And we are so hell-bent on pleasure that we seek it at the expense of happiness. Maybe it’s a notch in your belt that you drank this first growth. Where happiness comes from is in sharing wine with friends … The very successful sommeliers don’t just open bottles. They open the hearts and minds of people.”

Today, Singh says she channels the lessons she’s learned from her own experiences into her mentorship of others. “People just gravitate toward me,” she says. “I just keep my door open. I like to be very open about my own struggles, vulnerabilities, and shortcomings. I haven’t always gotten it right. It’s okay if you don’t know something. You can’t know everything.”

True Grit

Singh grew up in Monterey, California. Her parents, Indian-Fijian immigrants, owned and ran a small grocery store and worked in restaurants by night, her father as a chef and her mother waiting tables. In addition to that, her mother mentored other newcomers to the U.S.”, shepherding them through the immigration and citizenship processes and helping them find jobs. “My house was Grand Central Station—people always coming and going. It was the welcome wagon,” Singh recalls. “There was a couple from Fiji who lived with us for almost a year. I had to move out of my bed and sleep on the floor. I was like, ‘Can I please have my bed back now?’”

A strong student, Singh had ambitions to study political science at an institution like the University of California at Berkeley, but she couldn’t afford the tuition. She enrolled in a community college and began working in restaurants, aiming to earn enough to transfer to a larger institution. After talking herself into a job at a fine-dining establishment where the pay was especially good, she caught the wine bug, learned about the Court of Master Sommeliers, and dropped out of college at 19.

“I saw that I could educate myself,” she recalls. “The MS program had a built-in curriculum I could follow, and I was interested in the subject matter. I did a set of mathematics in my head—I didn’t want to be saddled with student debt. If I could pass this exam, I could write my own ticket.” Singh passed her Advanced Certification test two years later, and then, in 2003, she passed the Master Sommelier exam.

For a young somm with just four years of wine experience, it was a feat of extraordinary determination. “I have always worked, ever since I was a kid,” Singh says. “I don’t do relaxing very well.”

Singh’s drive is legendary, and those who have apprenticed under her say that her expectations are high, her attitude uncompromising. Behind the fun facade, there’s a taskmaster—but a taskmaster who demands just as much of herself as she does of others. Edy Orozco, an avid marathon runner who was tending bar at the time, struck up a deal with Singh five years ago: He would train her to run a half marathon if she would teach him about wine.

“At the beginning, I thought it was a joke,” Orozco recalls, “but she was really determined. She trained, and we ran the half marathon side by side.” He credits Singh with putting him on the path to his current position. A Certified Sommelier, he is the wine and beverage director at Bistronomic in Chicago. “Before 2013,” he says, “everything about wine was impossible to me. I thought you had to be super talented, like an artist, to be born with a gift. From Alpana, I found out that if you just study hard and practice, you can be a Master Sommelier.”

Modern Role Model

“I really do enjoy mentorship,” says Singh. The most important talks are not when they [aspiring sommeliers] are successful, but when they are not—coming back from the exam when they didn’t make the cut. I enjoy guiding people along and sharing how I dealt with the setbacks and the disappointments. It’s really important to tell people that you struggled just as much as they are struggling, that they are not doing anything inherently wrong.”

Despite the difficult reputation she may have made for herself earlier in her career, her acolytes and peers today describe Singh as humble and grounded. “I don’t think people realize that she is a really modest and empathetic person,” one sommelier told me. “She is really good about making sure that those under her are lifted up.”

Although he never worked for her, Fernando Beteta approached Singh for advice in 2003 as he began his own path toward a Master Sommelier pin. “She shared her study techniques, her experiences from previous exams, [and] motivation to get the jitters out,” recalls Beteta, now the director of education at Tenzing Wine and Spirits Company. Singh offered a mentorship, and Beteta says he most appreciated her raw honesty: “She would say, ‘It’s very hard to pass and then suddenly feel kind of lonely and depressed because you have put so much time and effort into accomplishing this thing … and then you don’t know what to do with yourself.

“I thought, if she could do it, I could. I initially reached out to her to ask how I could do it, coming from a similar background [Beteta is from Guatemala]—with no previous personal history with wine.”

Indeed, although Singh hasn’t gone out of her way to advertise herself as a poster child for diversity, her successes have had a profound impact on the industry, as well as society generally. When a South Asian mother and fan of “Check, Please!” approached her out of the blue to say, “You have no idea how much you mean to my family,” Singh was surprised to hear that she was a role model for the woman’s daughter. But she understood what the mother was alluding to. “I didn’t grow up with Mindy Kaling,” she says. “I didn’t have Aziz Ansari, Hasan Minhaj, ‘The Big Sick.’ We had Apu [the controversial character from “The Simpsons”]. I tried to make light of it: I’d joke, ‘At least he’s an entrepreneur!’”

In addition, “Alpana helped pave the way for ladies in the industry,” says Amy Lutchen, a Certified Sommelier and the wine director at Del Frisco’s steakhouse in Chicago. “For women, trying to work their way up in male-dominated places can be difficult—you’ll often be promised something that never comes to fruition.”

Lutchen, who was part of the opening team at Singh’s Boarding House, describes Singh’s management style as inclusive and fair. “She made everyone feel like part of a team right away and gave everyone an equal chance,” Lutchen says. “We all had to work almost every job. She wanted everyone in the restaurant to have experience in every position so that there was mutual respect among the entire staff.”

With her signature combination of humor and hard work, Singh has trained many of Chicago’s rising stars. After opening The Boarding House in 2012 and launching Seven Lions in 2015, she also opened Terra & Vine, a well-received Mediterranean restaurant in Evanston, just north of Chicago, in 2016.

Today, outside her restaurants, Singh serves as the chair of the 42nd Ward Democratic Organization in Chicago; works closely with Deborah’s Place, an organization that assists and empowers women facing homelessness; is a member of the Choose Chicago board of directors; and sits on the Advisory Council for the Illinois Restaurant Association. She is credited with playing a significant role in bringing the James Beard Awards to Chicago beginning in 2015. 

“For aspiring sommeliers looking for a role model,” says Evan Goldstein, “someone who came from a very modest start, Alpana has managed to carve herself a leadership role, and she has done so in a very positive way. She is an extraordinary woman.”

Katherine Cole is the author of four books on wine, including the new Rosé All Day. She is also the executive producer and host of “The Four Top,” a James Beard Award–winning food-and-beverage podcast on NPR One.

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