Hilary Duff Drops to Her Knees and Shakes Her Head After Whiskey Shot During Chicago Concert

_{Published by Cel Manero from Global One Media Inc.}

After taking the whiskey shot, Duff reacted with a grimace and exclaimed, “That was disgusting. Woah!” in a video posted to social media.

Hilary Duff got a memorable introduction to Chicago during the latest stop of her The Lucky Me Tour.

The 38-year-old singer and actress sparked laughs online after videos showed her struggling to handle a whiskey shot during her concert at Chicago on Sunday, July 26. Some fans, however, suspect the drink may have actually been the city’s famously bitter Malört.

In footage shared on social media, Duff appeared hesitant as she prepared for the shot.

“This part’s taking a lot longer than normal because I don’t want to do this alone,” she said before asking whether the whiskey was good. “I don’t even know what the difference is.”

In another clip, Duff confirmed that the drink in her glass was whiskey before raising it alongside her bandmates. She briefly removed her earpiece and spoke with one of her fellow musicians, who responded with an uncertain gesture.

Duff then turned toward her band and the crowd, lifted her glass and declared, “Cheers,” before taking the shot.

Her reaction came almost immediately.

After setting the glass down, Duff dropped into a crouched position and appeared to gag into her hand. She shook her head, reached for a bottle of water and stared toward the crowd with an unmistakably displeased expression.

She covered her mouth and waved her finger from side to side before reacting to the taste.

“That was disgusting,” Duff said with a shudder. “Woah!”

Although Duff identified the drink as whiskey, fans quickly began debating whether she had actually been served Malört, a liquor strongly associated with Chicago.

The account that shared one of the videos joked in its caption that Duff had discovered what happens when someone gives you a “whiskey” shot in Chicago, tagging Jeppson’s Malört.

According to the brand’s website, Jeppson’s Malört is a traditional digestif made with wormwood. The spirit was developed by Carl Jeppson during Prohibition in the 1920s and was marketed as a medicinal product. Its history allowed it to avoid certain restrictions because authorities reportedly assumed people would not consume it recreationally.

Production of the drink in its current form began in 1933. Malört has become particularly famous for its intensely bitter flavor and its connection to Chicago’s drinking culture. The brand describes it as a drink that has helped define the bar experience for many Chicago residents.

Fans were quick to weigh in on Duff’s reaction.

“I thought it was Malort,” one commenter wrote, while another asked, “Whiskey or Malort?!”

Someone else said they wanted confirmation that Duff had actually been given Jeppson’s Malört.

A TikTok video showing the moment from another perspective prompted similar speculation. One commenter joked that Duff had to be given Malört simply because she was performing in Chicago. Another person who claimed to have attended the concert said they immediately suspected the infamous local drink when they saw Duff’s reaction.

Other viewers sympathized with the singer, with comments including “Same Hilary, same” and jokes about how they probably would not have been able to finish the shot either.

A representative for Malört also joined the conversation, telling PEOPLE via email that although there was no way to confirm exactly what Duff had been drinking, her expression was certainly familiar to anyone who has watched someone take a shot in Chicago. The spokesperson added that they hoped Duff would always remember her “Windy City welcome.”

The whiskey-shot moment comes as Duff continues incorporating nostalgia into her The Lucky Me Tour. During the shows, she performs fan favorites including “Wake Up” and “So Yesterday,” while also performing “What Dreams Are Made of” live for the first time.

Duff previously explained to PEOPLE that one of the highlights of performing again has been seeing how strongly her older songs continue to resonate with fans.

She has also enjoyed seeing audiences connect with her latest album, Luck… or Something. According to Duff, the new music gives her and her longtime fans an opportunity to relate to one another from a more grown-up perspective.

“It’s this very cool way to connect in our lives now — everyone’s grown up, and we feel like we have a lot of the same life experiences,” she previously said. “It’s like more real-world s—, and it’s fun to mix those two together.”

The Chicago whiskey incident isn’t the first time Duff has had an entertaining reaction to food.

Earlier this year, she appeared on Mythical Kitchen’s Last Meals, where she introduced host Josh Scherer to a “disgusting food game” she plays with her 13-year-old son, Luca Cruz. Duff shares Luca with her former husband, Mike Comrie.