How 'Never Been Kissed' Pulled Off That Iconic Kiss Scene, According To The Cast & Crew

In 1999, the rom-com classic Never Been Kissed sent awkward, 20something journalist named Josie Geller (Drew Barrymore) back to high school to uncover the truth about teen culture. She saw it as a second chance to get adolescence right, hanging with the cool kids and going to prom. Instead, she fell hard for her dreamy English teacher, Sam (Michael Vartan), and learned that being cool isn't all it's cracked up to be. 20 years after its release, the rom-com has become iconic, and fans are still particularly obsessed with one of its scenes: the moment when Josie finally gets her kiss.

In the movie, Josie's story assignment takes a sharp turn when she challenges Sam to meet her at the baseball mound in front of the entire school and kiss her for the very first time. It's a romantic scene about a woman coming into her own, and the big kiss is unforgettable — not just for the millennials who grew up watching it at sleepovers, but for the people who made the movie. In honor of Never Been Kissed turning the big 2-0, cast and crew members Michael Vartan, Jordan Ladd, Abby Khon, Mona May, and Mary Ramos shared their memories of creating the kiss scene and their thoughts on the rom-com's enduring legacy.

Getting The Details Right

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From a custom-made dress to the perfect song (The Beach Boys' "Don't Worry Baby"), it's the details that made the big baseball stadium kiss such a special scene. But first, screenwriters Abby Kohn and Marc Silverstein had to think of the best way to make the moment pop.

Abby Kohn (Screenwriter): Once we solidified the idea of [Josie's] brother, Rob, coming in with his whole thing being, "I can get another shot at my baseball dreams," once we developed that story, it all came together as the perfect ending, and the perfect way to make it feel like a bigger, more exciting, more suspenseful thing than if it was just the two of them in a room.

Mary Ramos (Music Supervisor): Drew had a couple of songs she wanted to try to use in the film from the start — ["Don't Worry Baby"] was one of them. She loved the lyrics and the vibe. So, knowing the song beforehand helped to inform the way it was shot and edited — that great drumbeat intro as he's coming down the steps to her with the crescendo on the kiss. It was genius picture and music editing.

Mona May (Costume Designer): [The dress] was something that I designed. She's really gone through this transformation of the ugly duckling, and then she started finding herself. She has to strip everything away... and this is really her moment of, "I am who I am." So all of those elements went into the pink chiffon dress. It's cut on a bias, it had that little ruffle that was very feminine. We did her hair a little more curly, so it really was like a vision in pink on the green stadium. She also popped quite beautifully. And you know, it was the romantic end of the movie. It had to be beautiful, she had to look like an angel.

Filming The Electric Scene

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Because the big kiss takes place at a baseball stadium, the scene involved dozens of extras sitting in the stands.

Jordan Ladd (Gibby): There were a ton of extras there and the night was sort of electric — we knew what was happening in the scene, but it just had this incredible energy to it, and people really got into it. In fact, when they were shooting our side of things [in the baseball stands], Drew and Michael Vartan went out and did the kiss for us, so our reactions were authentic.

Michael Vartan (Sam): The baseball players in the scene I had become friends with were constantly trying to trip me as I left the dugout on "Action" for that scene, rolling bats or throwing gloves at my feet. One of them spit sunflower seeds on my shoe, it was hilarious.

Watching Drew Barrymore Take Charge

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Not only did the then-24-year-old Barrymore star in Never Been Kissed, it was also her first time as a producer.

May: It's such a dear film to me because it was her first producing movie with her company Flower Films. We finished The Wedding Singer and she wrote me a note and said, "can you please do it? It's my first movie, I want you to help me create this crazy character."

Vartan: Drew was wonderful, and one of the least "actory" actors I've ever worked with.. I was so impressed by her talent, composure, and the way she treated cast and crew alike, and her kindness, and also her kindness. Did I mention her kindness?

Ladd: It was very much a team, and because it was Drew's first movie in her production company, she would be at the monitors cheering people on, and it was like she really created an environment like a family. We all felt like her family.

Ramos: The most memorable moment was being in a meeting at Fox Studios at a big conference table with 18 executives, and at the head of the table was 24-year-old Drew as the producer of the film, calling the shots and making sure they knew that above all, she wanted this film to project positivity. That image of her happy, youthful power in that room is strong in my memory.

Seeing Never Been Kissed Become A Classic

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20 years later, the rom-com continues to be beloved and draw in new generations of fans.

Ladd: I really didn't know it was going to resonate as much as it has. In fact, I was watching Season 3 of Queer Eye, and they were making over this young man who was kind of a homeward bound, antisocial guy, shy. And Jonathan Van Ness was asking him about his romantic life and his romantic past, and he revealed that he had no romances to speak of. And Jonathan said something to the effect of, "Oh, is this kind of a Never Been Kissed situation?" And I though, oh my gosh, it's really… it's in the lexicon. How incredible! It's relevant today.

Kohn: I can talk to my 82-year-old dad who can connect with it, as can my 12-year-old daughter. There's this universal feeling of that super important time in our adolescence where everyone, no matter who were you, felt like, "oh God, I did some weird stuff and I made some weird choices...." Adolescence is so universally imprinted on us, and the idea that you could go back and do it over is so appealing.

May: There was something very dear about Drew's character that people fell in love with. People can really understand the struggle of falling in love, of love and deceit, and finding yourself and becoming who you are. Even now it's such a subject du jour: who are we as women?

Ramos: Sure, it was the '90s... so there may be a few dated cultural moments — I don't know that a romantic comedy where a high school teacher falls for a student and they end on a "happily ever after" kiss could be greenlit today without some kind of dark twist — but the fact that so many people have chosen to watch this film again and again means it worked and achieved what Drew wanted it to. I'm so glad to have been a part of it.

It's been 20 years since Josie's first kiss, but fans are still swooning over her iconic moment on that baseball mound, because some things, like allowing yourself to be open to the possibility of love, never go out of style.