Conan O’Brien met his match in Brooklyn bar owner Debbie, who hilariously joined his “SubwayTakes” episode on Tuesday with a two-minute riff session about how she was his “ex-wife.”
On the popular hot takes show, the former late night host rounded out his time with host Kareem Rahma by engaging with a passerby as she sat down next to Rahma. She asked him how he was doing, which was enough to get O’Brien cooking and the woman met him with her own “yes, and” at every turn.
“Yes, we go way back. We were married a long time ago,” O’Brien said when Rahma asked if they knew each other.
“We got too kids,” Debbie responded.
“How are they, by the way? I haven’t visited,” O’Brien continued.
Debbie played along perfectly and then her and the comedian were off to the races for the remainder of the show.
“They’re fine. One’s in medical school,” she said. “The other one’s in jail, but here we are.”
O’Brien apologized for not sending their children any money but the woman assured him it was find and that they still loved him.
“Do they really?” O’Brien asked incredulously. “I’ve never visited and I never paid for their education and the kids we had together, they still love me?”
“Pictures are everywhere in the house,” the woman responded to laughs from O’Brien. “Don’t worry. All they needed was pictures.”
He responded: “You were my happiest marriage. That was the best year and a half of my life.”
She assured O’Brien that she’d heard that same thing from her “other three husbands.” This had the comedian and the host laughing again and planning out a whole spinoff
“You are so funny … We’ve got our own show right here,” O’Brien said. “You’re absolutely fantastic.”
“You’re the new host, Debbie!” Kareem Rahma added.
The surprise guest then revealed that she owns a bar named Confessions Bar in Brooklyn’s Bedstuy neighborhood, joking that O’Brien has been thrown out of it twice.
To Rahma’s suggestion that he and O’Brien go to Confessions Bar later that night — and his request for a free drink — Debbie didn’t miss a beat.
“That sounds wonderful. 8He’s my baby’s daddy, he’ll get two,” she deadpanned.
Watch the comedian’s full “SubwayTakes” episode in the video below.
