Singh is a second-generation Indian American, born and raised in Monterey, California. Her parents are Fiji Indians who migrated from Fiji to California. The family owned and ran an ethnic grocery store. Her father was a chef for 30 years.
Singh's first job in the restaurant business (outside the family business) was as a waitress at Bakers Square. After an aborted attempt to join the US Air Force (due to a failed medical exam), she applied for a job at a fine dining restaurant but needed better background on wines. She self-educated and re-applied for the job, impressing the interviewer, who hired her and encouraged her to continue her studies. She became a sales clerk at Nielsen Bros. Market in Carmel, California which further exposed her to the wine business.
Singh passed the Court of Master Sommeliers' advanced certification test at age 21. In 2003, she passed the final exam to become the youngest woman ever to achieve the rank of Master Sommelier. (The master sommelier exam has an approximately 3% pass rate.)
Beginning at age 23, she served as sommelier at Chicago's restaurant, Everest. She later became Director of Wine and Spirits for Lettuce Entertain You Enterprises, a large Chicago-based chain of restaurants.
Singh became especially well known for hosting the local Public Broadcasting Service (PBS) public television station WTTW's restaurant review show, Check, Please! and her regular appearances on Chicago Tonight for the "Ask Alpana" segment on Thursday evenings. She replaced the original host of Check, Please!, Amanda Puck, in October 2003 and remained in that role until 2013, when she was replaced by Catherine De Orio.
Singh authored the 2006 book Alpana Pours: About Being a Woman, Loving Wine, and Having Great Relationships (ISBN 0-89733-546-5) and writes a column on wine for RedEye.
In December 2012, Singh opened The Boarding House, a wine-driven concept in the River North neighborhood. The four-story restaurant received national attention from Forbes Travel Guide (Top 40 Tastemakers), Food & Wine (Sommeliers of the Year), Market Watch, Sommelier Journal, Restaurant Hospitality, Midwest Living and more. Additional accolades include "100 Best Wine Restaurants" (Wine Enthusiast), "Pastry Chefs to Watch" (Time Out Chicago), "2013 Best New Restaurants" (Chicago Magazine), and nominations for best restaurant design from the Eater Awards and Jean Banchet Awards. Singh closed out the restaurant’s first successful year with an all-female culinary and beverage team, and the honor of Sommelier of the Year 2013 Wine Star award from Wine Enthusiast magazine.
In 2014 and 2015, Singh appeared as a judge on the Food Network show Food Truck Face Off. The television show premiered just prior to Singh running her first marathon and opening her second restaurant, Seven Lions, an American concept, located on Chicago's Michigan Avenue.
In 2006, Singh married fiction writer Charles Blackstone. They divorced in 2014.2006 Wine & Spirits Professional of the Year by Bon Appetit magazine
Best Sommelier in America by Wine and Spirits magazine
Crain's Chicago Business 40 Under 40
Food & Wine's 35 Under 35
Best Sommelier (2004) by Chicago magazine
30 Under 30 (2006) by Jane magazine