Adam Sandler marked his 23rd wedding anniversary with a big surprise for his wife, Jackie. The 59-year-old actor hired a skywriter to spell out a heartfelt message in the sky above what is believed to be their home in the Pacific Palisades area of Southern California.
The message in the sky showed the number of years the couple has been married, along with a heart placed between their initials. It read, “23 A [loves] J.” Sandler posted a photo of the skywriting on X the same day, along with a warm caption.
He wrote, “Happy 23rd anniversary to my sweetheart. Love you forever.” The caption, paired with the photo of the message above their home, quickly drew attention from fans and followers who follow the couple’s relationship.
The anniversary surprise comes after comments about the couple’s red carpet outfits
This public show of love comes after a period when the couple faced some comments about their clothing choices. In late May, Sandler went to the premiere of the romantic comedy Office Romance to support Jackie, who stars in the film with Jennifer Lopez and Brett Goldstein. Jackie wore a black, sparkly minidress with a keyhole cutout, while Sandler stuck to his usual relaxed style.
He showed up in a large, orange New York Knicks hoodie paired with bright blue sweatpants. This outfit led to some criticism online, with some people saying he was embarrassing his wife. Sandler has long been known for choosing comfort over dressy clothing.
He spoke about his dislike for formal outfits during a press tour for his movie Jay Kelly. He told Entertainment Tonight last fall, “It’s been horrendous.” When asked what exactly bothered him about formal clothing, he said, “I don’t like the feeling.” He also added, “I can’t stand the pants. I can’t stand the jackets, the stupid shirts. Hate them all.”
Even with the talk about his outfit at the premiere, the couple appears to be just as strong as ever. They soon stepped out together to show they were on the same page, attending two New York Knicks games at Madison Square Garden on May 31 and June 10. The two were seen sitting courtside during the NBA Finals, watching the Knicks beat the San Antonio Spurs in Game 5 to win the championship.
They were not the only famous faces courtside, as Taylor Swift also cheered on the Knicks during the Finals run. The city’s excitement around the team also reached local politics, with Mayor Mamdani’s stance on attending games drawing attention during the same playoff run.
Sandler and Jackie have a long history together, reports the Daily Mail. They first met on the set of Big Daddy in 1999, dated for four years, and got married in Malibu on June 22, 2003. Over their 27 years together, they have built a family and have two daughters, 20-year-old Sadie and 17-year-old Sunny.
While Sandler is known for dressing casually at big events, he has shown he can dress up when needed, such as wearing suits to promote his films alongside co-stars like George Clooney. The anniversary message in the sky shows that the couple continues to focus on their relationship, regardless of any comments from people online.
Published: Jun 23, 2026 10:30 am