The 45-year-old actress and 54-year-old actor reprised their characters, Lucy Whitmore and Henry Roth, during a segment for The Drew Barrymore Show premiere Monday.
50 First Dates followed the romance between Lucy (Barrymore), a woman suffering anterograde amnesia after a car crash, and Henry Roth (Sandler), a womanizing veterinarian. The pair fall in love and marry, with Henry making tapes for Lucy to remind her of their memories together.
On The Drew Barrymore Show, Barrymore and Sandler reunited to create a new tape for Lucy.
"Hi Lucy, good morning! It's me, Henry," Sandler says as Henry. "We are on, I think, our 5,000th date together and it's been great. I want to catch you up."
"You have a thing called amnesia and I am your husband. We have a daughter and she's about 40 now, or something like that," he adds.
Henry then updates Lucy on the events of 2020.
"It's 2020. We're all still in the middle of a pandemic, which is a terrible thing. Baseball games are now being played in front of cardboard people," Sandler says.
"I couldn't honestly be more excited for you. You have your own show now," he adds before Allen Covert interrupts the pair as his character, Ten-second Tom.
Barrymore launched a digital series prior to the Drew Barrymore Show premiere. In one segment, the Art of the Interview, Barrymore spoke to Whoopi Goldberg this month about how they bonded on the set of the 1995 film Boys on the Side.
Sandler will star in the new Netflix movie Hubie Halloween. The streaming service shared a trailer for the comedy last week.