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Drew Barrymore and Adam Sandler have undeniable chemistry on and off-screen. Their celebrity relationship has led to some of the best romcoms and made them a beloved duo in the genre. Given the actors’ convincing performances in multiple movies, fans wonder, did Drew Barrymore and Adam Sandler ever date in real life?

Drew Barrymore and Adam Sandler co-starred in multiple movies

Did Drew Barrymore and Adam Sandler date?
Adam Sandler and Drew Barrymore during Super Bowl XXXVIII in 2004 | Jeff Kravitz/FilmMagic

Adam Sandler is known for casting his friends in most of his projects. He has worked with Rob Schneider, Kevin James, Chris Rock, and David Spade. Drew Barrymore became another frequent collaborator when she co-starred with Sandler in the 1998 comedy The Wedding Singer. But landing the part opposite the comedian wasn’t easy.

Barrymore had been blacklisted from Hollywood after finding fame in movies such as E.T.: The Extra-Terrestrial. On the other hand, Sandler’s star was on the rise, and Barrymore thought they were too different. Still, she wanted to make movies with the Saturday Night Live alum and, according to her, had to “beg, borrow and steal” to land a meeting.

Thankfully, Sandler found Barrymore charming and a total “badass,” so he cast her in his 1998 film, The Wedding Singer. The movie was a success, earning $123 million and several awards.

Sandler and Barrymore teamed up again for 50 First Dates. The 2004 movie was an even bigger hit, earning nearly $200 million at the box office against a $75 million budget.

A decade later, the pair shook the success tree again with 2014’s Blended. It made $128 million against a $45 million budget. The film marked Sandler and Barrymore’s last on-screen collaboration.

Did Drew Barrymore and Adam Sandler ever date?

Many fans have long interpreted Drew Barrymore and Adam Sandler’s connection as lust or romance. But the two actors have neither confirmed nor denied any romantic feelings. However, Barrymore revealed in an interview on The Howard Stern Show that she and Sandler “never, ever, ever” dated.

The Never Been Kissed star heaped praise on her on-screen partner, calling him a “handsome dude” and saying she was more “attracted to his inner light.” Barrymore acknowledged he was incredibly talented, saying, “talent is sexy.” She noted that her attraction to Sandler involved their ability to create something “meaningful” together as co-stars.

Sandler told Stern that working with Barrymore opened doors for him in the romcom field. “Drew liking me made it seem like girls were allowed to like me in movies,” the Murder Mystery star said.

And in a 2014 appearance on Chelsea Lately, the two asserted that they never saw each other in a romantic light. Sandler even joked that he tried to get Barrymore to examine his privates at one point.

What are the 2 stars doing now?

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After her final film with Sandler, Barrymore didn’t take many acting jobs, appearing only in Miss You Already, Santa Clarita Diet, and The Stand-In. In 2021, she announced she was taking a break from acting to spend more time with her children.

The Charlie’s Angels actor explained she had spent her entire life in front of the camera. But after having her daughters, Olive and Frankie, she felt the time was right to “put making movies on a back burner so that I can be present and raise my kids myself.”

Despite stepping away from acting, the star has hosted The Drew Barrymore Show since 2020. Earlier this year, CBS renewed the talk show for a third season. She also has a popular housewares line with Walmart.

Sandler, on his end, has also remained busy. He has appeared in projects such as The Ridiculous 6, Uncut Gems, and Hustle. He also lent his voice to the Hotel Transylvania franchise as of the main characters, Dracula.