36 Fascinating Facts About 'Serendipity' You Didn't Know

It was at their audition for the film — and that's all that was needed to confirm their undeniable chemistry. "I met Kate once before, but sometimes you meet people and feel like you've known them for ages," John told BBC. "That's what actors have to do. It's great, it's like an affair without the mess!"

When you really think about it, Jonathan and Sara rarely interact in the movie, despite being the two main characters. Since they only appear together in a few scenes, John and Kate didn't see each other much during production.

"It started out that Sara was American when I first met Peter [Chelsom]," Kate told The Telegraph. "I auditioned in American, and he said, 'Now we can try it in an English accent?,' and I was terribly offended! I think he decided it would be a hoot to have an English girl." Honestly, the film would have felt so different if Sara was American, don't you think?

In fact, she was days away from having her baby. "I was more pregnant than you can be: I was three days overdue," she told The Telegraphy. "But I told them I was pregnant, and I had these giant boobs and blonde hair, and then suddenly I didn't anymore. I think that was what Peter [Chelsom] actually liked."

Yep, the rom-com queen herself. "I distinctly remember Jennifer Aniston coming in to meet us. I remember when she came in, she said, 'I do a romantic comedy once a week,' her being on Friends at the time," director Peter Chelsom told Insider. "So, she clearly had other things on her plate, and it was her decision not to do it. She came in good faith without an offer, but we definitely would have made her an offer if she wanted to make it."

The Spy Kids actress made it all the way to the final stages of auditions. She made such a great impression on director Peter Chelsom, he casted her in his movie The Space Between Us years later.

Specifically, the hottest part of August. The layered costumes made for some sweaty actors, all of the snow was all fake, and 350 extras were relied on to make the backgrounds of the wintry scenes seem more realistic. "The biggest challenge was creating Christmas in its signature location, which is Wollman Rink, the skating rink in Central Park. It had to look and feel cold,” producer Simon Fields told cinema.com.

It's not easy to ice skate on, well, fake ice. "I used to have skating lessons when I was a kid, so at first I was all confident about it, but it was a whole different deal. It was pretty hard to skate on and much different than being on real ice," Kate told cinema.com. It wasn’t much better for John: "I'm not a skater and that was kind of nice because my character doesn't know how to skate. So I didn't have to take any lessons. I just strapped them on and went."

The warm weather came with challenges that went far beyond making the ice rink look realistic. "We had some bad weather and there was mosquito spraying in the park that actually forced us to shut down a few times," producer Peter Abrams told cinema.com. "So, that sort of threw us a monkey wrench. But, the crew was wonderful and we were able accomplish what we needed."

In fact, it wasn't filmed in New York City at all. Those now-iconic elevators are part of the Fairmont Royal York Hotel in Toronto.

When the actress found herself back at that very same hotel in 2019, she acted out the scene with an employee. "He was a real sport in the end. John Cusack should watch out because he crushed it," the actress told Jimmy Fallon.

Just two days after September 11, 2001, the first version of Serendipity — with images of the Twin Towers — debuted at the Toronto Film Festival to a very shocked crowd. The Chicago Tribune reported the skyline shots "caught some audience members off guard," so the studio digitally edited them out. "I don't think [the audience] wanted to see those images anymore," John told The Telegraph. "They just wanted to feel something else."

Not only were the actors sipping on Serendipity 3's (delicious!) signature Frozen Hot Chocolate, but they shot in the real restaurant. The famous location has since named their table the Star Table, turning it into a must-visit destination for tourists.

It was "challenging," director Peter Chelsom revealed to Insider. "John kept looking at me like, 'Oh God, what are we going to do?' Because Eugene was overplaying it. We took a break and I pulled him aside and I said: 'Relax, the laughs will come by virtue of the situation, don't push it.'" Clearly, the director's advice worked.

Speaking of Eugene Levy, he was getting ready for his big confrontation scene with John Cusack at Bloomingdale's, when he was told to say "chase me" and run behind the counter. "John Cusack then said, 'That is the most bizarre note any director has given any actor.' Eugene then said, 'Two hours ago you told me not to be over the top.' So they aren't into it and I said, 'Look, we'll get the crew in to watch the rehearsals if they laugh it's in the movie, if they don't laugh it's not in the movie,'" director Peter Chelsom revealed. Clearly, the crew laughed.

When filming in New York City, it's common to have curious onlookers watching from afar. That's why producers posted a note on their trailer with this message: "Yes, we are filming a movie. It is called Serendipity. It stars John Cusack and some girl from Britain that you wouldn't know – even if we told you her name. We will be shooting tonight until midmorning. Please don't ask the crew any questions. Even if they don't look like they are working, they are thinking."

The actors were inseparable as kids and grew up attending a theater school run by Piven's parents. Unfortunately, their close bond reportedly came to an end after Jeremy booked Entourage. In 2007, he hinted that his former friend became jealous, telling Best Life magazine: "It just says so much about a person if he has space for other people's success." John denied the allegations, arguing, "It's quite the contrary. I am very happy for Jeremy. I wish him the best and I always have." To this day, where they stand with their relationship remains unclear.

Listen carefully, and you might hear Jonathan call Dean "Gerald" without any context behind the choice. That's because Gerald was John Cusack's real-life nickname for Jeremy Piven. Whether it was done on purpose as a joke or producers just didn't notice it, the line was kept in the film.