“I think it has to do with my teeth, the way I nod my head, my expression,” he said. “Also, you don’t need to speak a specific language to enjoy the content.”
Which might explain the culinary challenges proposed by international fans, like a 2023 U.S. versus Thailand McDonald’s “showdown,” for which he and Pappas traveled to Asia to investigate which country’s menu items appealed more. Together, Pappas and Winkler have traveled to more than a dozen countries for food challenges.
“Tommy was made for this life,” said Pappas, who goes by Jess. “I think it’s so cool.”
Both are careful not to let the serious business of eating take precedence over their relationship. Winkler regularly references their relationships in his TikToks, such as a 2023 video in which he forks up chicken tikka masala. “I am in love with Indian food and @jessica.pappas,” the caption reads.
Her content, including a podcast the couple started hosting together this year, “Don’t Ask with Jess and Tommy,” covers relationships, pop culture, fitness — and their devotion. “He’s steady and so supportive,” she said.
Winkler and Pappas live in a townhouse in a Chicago suburb with four cats. On June 6, 2025, he asked her to marry him on a walk at the Alfred Caldwell Lily Pool in Chicago’s Lincoln Park.
On May 29, 100 guests gathered at Meyer’s Castle in Dyer, Ind., to watch the couple marry. The groom’s brother, Jonathan Winkler, who had been ordained by the Universal Life Church for the occasion, officiated. At the reception, guests were served chicken marsala, filet mignon and tiramisù.
The groom, who normally shoots his own content, didn’t film himself eating any of it.
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