We’ve all had disastrous first dates, but how many of us can say that our less-than-stellar first impressions have led to a happy marriage? When comedian Jon Stewart stopped by the Strike Force Five podcast this week, he recounted the endearingly awkward story of first meeting his now-wife, Tracey McShane.
Co-host Stephen Colbert asked Stewart what he thinks McShane might say if asked to recount the story of them falling in love, and Stewart cited their first, slightly disastrous, dinner date at Lupe’s Kitchen in East Los Angeles.
“When she gets nervous, she gets very quiet. When I get nervous, I get the opposite,” he said. Stewart interpreted her quiet demeanor, and that she wasn’t eating her meal, as a sign that the date wasn’t going as he’d hoped.
“This girl that, I thought, truly not only didn’t like me, but found me repulsive,” he said, caused Stewart to scarf down “two giant burritos — hers and mine.”
“I apparently nauseated her, she didn’t touch her food, so I threw it all down,” he said, much to the podcast hosts’ delight.
But Stewart turned the night around when they went to a nearby bar after dinner for a second try. He recalled, “Two shots in, she relaxes,” and McShane started to become chattier. This was when Stewart realized how funny and smart she was.
“Then and there, I wrote her a note,” he recounted. “It said, ‘Would you be my girlfriend?’ And I gave her only two boxes that she could check. One was ‘yes’ and the other was ‘of course.’”
The hosts of the show texted McShane directly for her side of the story to the original question of how Stewart fell in love with her. Her answer?
“I think when he got a few drinks in me, which got me to finally speak,” she recalled.
Strike Force Five finds five of the most prominent late-night talk show hosts — Colbert, Jimmy Fallon, Jimmy Kimmel, John Oliver and Seth Meyers — teaming up for a podcast about the inside scoop of late-night TV. The podcast was created to support the out-of-work staff of each host’s program while the WGA and SAG-AFTRA strikes continue to affect Hollywood.
Strike Force Five is available to listen to on Spotify and all major podcast platforms.