NYC Bar Owner, 68, Wins Over Conan in Viral Subway Chat

WHO:

NY Post - Debbie Shields owns Confessions Bar in Bedford-Stuyvesant, Brooklyn, and had a viral subway conversation with comedian Conan O’Brien on Kareem Rahma’s online series, “Subway Takes.”

Bored Panda - Shields was traveling with her friend Tony, who was a Conan O’Brien fan; Rahma was filming O’Brien for “Subway Takes.”

Bored Panda - O’Brien told Shields, “You are so funny,” and said, “We’ve got our own show right here.” Rahma jokingly called Shields “the new host.”

Bored Panda - Shields told The New York Times she introduces performers at weekly comedy nights at her bar but has not regularly performed stand-up. She said, “I just might do [start doing stand-up], because it sounds interesting.”

Bored Panda - Shields told CBS News, “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.”

WHAT:

Bored Panda - During an 89-second exchange, Shields and O’Brien improvised a fictional marriage and family history. They joked that they had two children—one in medical school and one in jail—and that Shields had three other husbands.

Bored Panda - Shields said the clip’s spread brought customers to Confession Bar to meet her. She described the change by saying, “One minute and 29 seconds changed my life.”

Bored Panda - Shields introduced a specialty cocktail called “The Baby Daddy O’Brien,” inspired by their fictional-family joke.

Bored Panda - Shields said O’Brien might visit her bar for karaoke; his visit was not confirmed.

WHERE:

NY Post - The conversation took place aboard the F train in New York City.

Bored Panda - Shields and Tony transferred from the A train to the F train and spotted O’Brien filming.

Bored Panda - Confession Bar is in Brooklyn’s Bed-Stuy neighborhood.

WHY:

Bored Panda - Tony’s admiration for O’Brien prompted Shields to approach him. Shields told The New York Times, “I said: ‘Well, you hold the seat for me and I’m going to go sit next to him.’”

HOW:

Bored Panda - Shields played along when O’Brien claimed they had once been married, improvising quick responses that made him laugh and helped the clip spread on social media.

Bored Panda - Shields told CBS News that people who once said, “Get out of the way, old lady,” now tell her, “I seen you on TV. We love you.” She added, “I love you, too.”

(UPDATED October 25, 2026 07:59 UTC)

A Brooklyn bar owner has become an unexpected online sensation after a playful subway exchange with comedian Conan O’Brien. Debbie Shields was riding New York’s F train with her friend Tony, a fan of O’Brien, when they spotted him filming Kareem Rahma’s “Subway Takes.” Tony encouraged her to approach, and Shields quickly joined O’Brien in inventing a shared marriage and family history. In the 89-second conversation, they joked about two children—one in medical school and one in jail—and Shields having three other husbands. O’Brien praised her humor, while Rahma jokingly called her “the new host.” The clip brought new customers to Shields’s Bed-Stuy bar, Confessions, where she introduced a cocktail called “The Baby Daddy O’Brien.” Shields says the attention has changed how people treat her, and she may even try stand-up comedy. A possible karaoke visit from O’Brien remains unconfirmed.