A chance encounter on a Brooklyn subway has transformed the life of bar owner Debbie Shields after her 90-second exchange with Conan O’Brien became an internet sensation.
Shields, 68, was traveling through Bed-Stuy with her friend Tony when they switched from the A train to the F. There, they spotted O’Brien filming an episode of Kareem Rahma’s viral Subway Takes.
Tony, a longtime O’Brien fan, encouraged Shields to approach the comedian, she told The New York Times. “I said: ‘Well, you hold the seat for me and I’m going to go sit next to him.’”
She walked over, greeted O’Brien and took the seat beside him. “I said, ‘Hey, Conan.’ He said, ‘Hey, how you doing?’ And I sat down and went on from there,” Shields recalled.
When Rahma asked O’Brien whether he knew Shields, the comedian instantly improvised a story, joking that the pair had been married years earlier.
“Right, a long time ago. We got two kids,” Shields replied, enthusiastically joining the gag.
“How are they, by the way? I haven’t visited,” O’Brien shot back.
“They’re fine. One’s in medical school, the other one’s in jail,” Shields answered without hesitation.

Debbie Shields, 68, of Brooklyn, became an overnight sensation after appearing in 1.5 minutes of a viral Subway Takes video.

Her unexpected celebrity began when she boarded the F train and decided to greet Conan O’Brien, who was appearing as Kareem Rahma’s guest on Subway Takes. “One minute and 29 seconds changed my life,” the mother-of-three said.
“I’m sorry I’ve never sent any money,” O’Brien continued, keeping the fictional family history alive.
“It’s okay, they still love you,” replied Shields, who owns Confessions Bar.
The playful exchange continued as fellow passengers looked on. O’Brien burst into laughter while the impromptu performance unfolded around them.
“You were my happiest marriage, that was the best year and a half of my life,” O’Brien said.
“I’ve heard that from my other three husbands too,” Shields replied, prompting another round of giggles from the comedian.
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The brief subway encounter quickly propelled Shields into the spotlight. Soon, customers were showing up at her Bed-Stuy bar specifically hoping to see the New York comedy sensation.
“One minute and 29 seconds changed my life,” Shields, a mother of three, told CBS News.
The attention has even prompted Shields to think about trying comedy herself. She already hosts weekly comedy nights at Confessions Bar, making it a natural place to test out her new ambitions.

Rahma has since stopped by Shields’ Bed-Stuy business, Confessions Bar.

Since the clip, Shields is now considering picking up stand-up comedy
‘I do go onstage and introduce the comedians, but that’s my limit,’ she told the Times. ‘I just might do [start doing stand-up], because it sounds interesting.
‘I love to make people laugh. I love to have fun. I love to enjoy life, because life is beautiful. It’s what you make it.’
The entrepreneur said she even laughs at funerals, causing her friends to say they can’t be seen together, she told CBS.
Since the clip was posted to social media, Rahma has visited the bar, where he took a photo of the two together.
As for O’Brien, Shields said he might stop by for karaoke on Saturday.
‘He says he can clear a room with his singing, so watch out,’ she told CBS. ‘It should be very interesting.’
And even if he doesn’t make his way to the Bed-Stuy bar, he’s already left his mark. On the menu, Shields now serves a drink called The Baby Daddy O’Brien.
Our News Outlet has reached out to Shields for comment.