What would you be willing to do to make new friends? Would you sit down to dinner with a group of complete strangers? Brook Anderson, the founder of Second Helping Supper Club, believes that sharing a meal is one of the fastest ways to break the ice and spark genuine connections.
When Anderson, a native Minnesotan and passionate home cook, moved to Chicago in early 2020, she didn’t know a soul in the city. Over time, as her circle of friends grew, she began hosting dinner parties and soon realized they were more than just meals—they were a chance to connect with intention and care. Anderson scaled that notion city-wide in 2024, when she launched Second Helping Supper Club, a series of pop-up dinners and events hosted at various secret locations throughout the city.
“I hope that people feel that for one night they were included in something,” Anderson says of Second Helping Supper Club’s ethos. “That feeling of connection can be so fleeting and rare I hope more than anything that [diners] feel like they did something unique and different.”
Since its inception, Second Helping has expanded beyond its flagship communal dinners by dabbling in pop-ups—think one-day café concepts and concession stands at beachside concerts. Anderson also produces an event series dubbed “Second Hangs,” a gathering open to previous attendees of Second Helping’s communal dinners with themes like Weenies & Tinis (gourmet hot dogs washed down with ice-cold martinis) and Bagel Boy Brunch (homemade bagels shellacked with schmear and coupled with candy-colored cocktails).
With just over a year of Second Helping events behind her, Anderson is proud to report several relational success stories: Friend groups have formed and dates have materialized. During my conversation with Anderson, she coyly shared that many singles (most of them women) frequent her events. “It’s the perfect spot to meet someone,” she said with a wink.
I had the opportunity to attend Second Helping’s Mexico Meets Midwest event—a reprisal of Anderson’s dinner series in collaboration with chef Itzel Hernandez—earlier this month. As its name suggests, the menu revolves around Anderson’s childhood spent in the Midwest tending to the family garden and canning fresh produce with her grandmother and Chef Hernandez's Mexican heritage. Tickets to the event were $105—with a portion of proceeds benefiting Midwest Immigration Bond Fund—and included a six-course meal paired with a generous pour of Mexican rosé sourced from Vinoteca, a Latina-owned wine shop in Avondale.
I met my fellow diners in a conversation area where we shared crisp crudité and sikil pak, a silky blend of pumpkin seeds dusted with an earthy dukkah crunch. I was surprised to learn that, despite the emphasis on meeting strangers, I was the only solo diner in attendance—all other attendees were couples and cliques bunched in groups of two to four. After we all became acquainted, Anderson ushered us to a table glowing with candlesticks melting into silky ropes, and offered a “table question” (“What was your favorite cartoon growing up?”): an icebreaker she incorporates into every communal dinner.
Throughout the two-hour meal, chef Hernandez shared personal anecdotes—like her oyster-based tribute to her father, who grew up in the sunlit coasts and bustling fish markets of Puerto Vallarta—and regional context to introduce each dish. The night's conversation ebbed and flowed, at times a little tangled, but it was clear where genuine connections were taking shape—even if not across the whole table. Anderson spent the night plating and clearing dishes, occasionally slipping into conversation, more often offering a contented smile as guests softened in the warmth of full stomachs and empty wine glasses.
“The most important part is how we’re staying connected.”
The night ended in the conversation area where we all began as strangers, and we signed the Second Helping “guest book,” a journal bulging with collaged Instax photos and torn scraps of craft paper inscribed with messages from past diners. I signed the book while snacking on a surprise plate of wonderfully fruity mole truffles made by chef Hernandez. While I didn’t walk away with any new friendships, it was still an evening of rich connection—and, of course, phenomenal food.
As far as the future goes, Anderson hopes to continue fostering the Second Helping community and hosting even more adventurous events while supporting local charitable organizations like Pilsen Food Pantry. “I think it’s easy to get carried away with the profits of it all,” she says. “But the most important part is how we’re staying connected.”
For those interested in attending a Second Helping Supper Club dinner or pop-up, events are announced on a rolling basis via Instagram and TikTok.