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Jon Stewart Recalls Disastrous First Date With Wife Tracey McShane: ‘I Apparently Nauseated Her’

Jon Stewart Recalls Disaster First Date With Wife Tracey McShane
Jim Spellman/Getty Images

John Stewart has been married to wife Tracey McShane for 20 years, but their first date was a disaster.

Stewart, 60, shared the harrowing tale of the couple’s first encounter during the Friday, September 22, episode of the “Strike Force Five” podcast. He recalled taking it personally when McShane, 56, didn’t dig into her meal at the Mexican restaurant where they went for their inaugural outing.

“I apparently nauseated her, she would not touch her food, so I threw it all down,” the former Daily Show host said, noting that he finished “two giant burritos, hers and mine.”

Despite fearing that McShane “not only didn’t like me, but found me repulsive,” Stewart wasn’t quite ready to give up on the date, so he suggested they stop in at a nearby bar.

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“Two shots in and she relaxes,” he told podcast hosts Stephen Colbert, Jimmy Fallon, Jimmy Kimmel, Seth Myers and John Oliver, noting that he now knows his wife “gets very quiet” when she’s nervous. “Once she started talking and [I realized] how funny and smart she was? Oh, my God.”

Colbert, 59 — who has been friends with Stewart since they worked together on The Daily Show in the late ‘90s and early aughts — recalled reaching out to McShane after the date to hear her version of events. According to Colbert, McShane told him, “I think when he got a few drinks in me, it got me to finally speak.”

Stewart previously revealed that McShane’s roommate, whom he met while working on the 1997 film Wishful Thinking, set them up on a blind date.

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“The way she described [Tracey] was in such glowing terms, I thought, ‘Well, I’d be a jackass not to go out with this woman.’ So, I called her,” the comedian said during a 2002 appearance on Larry King Live.

When Stewart was ready to pop the question, he recruited New York Times crossword editor Will Shortz to help him create a crossword puzzle with clues leading to the proposal.

“Crossword puzzles [are] a real bond for us,” Stewart told the Los Angeles Times in 2006 of the romantic engagement. “It is a constant reminder that I am married to a very smart woman.”

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The duo tied the knot in 2000 and welcomed son Nathan and daughter Maggie in 2004 and 2006, respectively. Stewart and McShane also cofounded an animal sanctuary in 2015, the Hey Friend Foundation in New Jersey.

Stewart’s love of animals stood out to McShane early in their relationship. During a 2015 interview with the New York Times, she recalled being impressed that Stewart had inherited two cats from a past relationship.

“The fact that he got custody of the cats said so much about him,” she said. “This was my dream man.”

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