Unexpected Journeys: Catching Up with the ‘Serendipity’ Cast - Kate Beckinsale, John Cusack, and Beyond!

In 2001, fans of romantic comedy witnessed the captivating journey of Kate Beckinsale and John Cusack's characters in the heartwarming film "Serendipity." The story revolves around Jonathan Trager and Sara Thomas, who, after meeting, falling in love, and parting ways, embark on a long search for each other in the bustling city of New York. Despite the heartbreak of their separation, they firmly believe that their initial encounter was destined to be.

"There was a central issue with the female character's believability, which we discussed extensively in meetings. I wanted to avoid portraying her as a foolish and ethereal figure, despite her strong fascination with fate," Beckinsale shared in an interview with Vulture in April 2020. "Being interested in fate doesn't automatically make someone supernatural and dreadful. In fact, she's a therapist. It was important for her to be a competent and respectable therapist, while also maintaining her obsession with serendipity and destiny. Balancing these aspects of her character was crucial to avoid making her appear completely implausible. It's possible to be whimsical, positive, and intelligent at the same time."

Beckinsale affectionately reminisced about her experience filming in Manhattan as a native of England.

"We found ourselves in New York City in the midst of August, wrapped in scarves and overcoats, sweltering under the heat and feigning ice-skating on linoleum instead of real ice," she shared with the media outlet. "I recall feeling unbearably hot throughout the entire experience. It was like being in a quintessential Christmas movie, only with everyone drenched in sweat."

This beloved actress, known for her role in "Pearl Harbor," has embraced the opportunity to revisit and recreate iconic scenes from the film, including the memorable elevator moment, despite the reluctant participation of a hotel staff member.

"I immediately recognized the elevators in the hotel where I was staying," she wrote in the caption of her Instagram clip in September 2018. In the clip, she recited a nostalgic dialogue from the film "Serendipity." She revealed that the hotel was the same location where the film was shot. However, she expressed disappointment in not being able to convince her leading man to participate in this nostalgic moment. "@fairmontroyalyork." The film's director, Peter Chelsom, also reflected on the filmmaking process, sharing insights nearly two decades after the movie's release.

"We envisioned a world in our film, a world we yearned to see become a reality," Chelsom shared with Insider in October 2021. "It is devoid of time constraints and devoid of starry night skies. All these facets contribute to its ability to transport you, allowing for ultimate escapism. It centers around the delicate balance between a man and a woman, both facing similar challenges: the pursuit of an ideal partner that ultimately proves unattainable. In the early 2000s, many films, which I had criticized at that time, tended to exhibit sexist tropes. The plot formula often revolved around a misbehaving 'frat boy' who hits a breaking point in the second act, only to spend the entirety of the third act apologizing to a beautiful blonde. This formulaic laziness of romantic comedies culminated in Serendipity."

Keep scrolling to discover what the cast of Serendipity has been up to since the beloved holiday romantic comedy premiered in 2001:

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‘Serendipity’ Cast: Where Are They Now? Kate Beckinsale, John Cusack and More

Is it meant to be? In 2001, romantic comedy fans followed the would-or-wouldn’t-they romance of Kate Beckinsale and John Cusack's lovestruck characters in Serendipity.

The film follows the story of two characters, Jonathan Trager and Sara Thomas, who meet, fall in love, and then go their separate ways in New York City. Despite their heartbreaking separation, both characters remain convinced that their initial encounter was meant to be.

During an interview in April 2020, Kate Beckinsale, who played Sara Thomas, discussed the challenge of making her character believable. Beckinsale wanted to avoid portraying Sara as a wispy fool, despite her strong belief in fate. She wanted to depict Sara as a therapist who is both interested in serendipity and fate, without making her seem completely implausible. Beckinsale aimed to create a character who is whimsical, positive, open, and intelligent, while also being a competent therapist.

The native of England nostalgically reminisced about her time filming in Manhattan.

"We found ourselves in New York in August, wearing scarves and overcoats, drenched in sweat and pretending to ice-skate on linoleum because it was too hot for real ice," she recalled in her conversation with the outlet. "I can vividly remember how hot it was all the time. It was like a typical Christmas movie, except we were all sweating profusely."

The actress from Pearl Harbor has a familiar connection to a particular scene in the movie. In September 2018, she shared a video on Instagram where she reenacted the memorable elevator scene. She mentioned staying at a hotel that had the same elevators as in the film, lamenting that her leading man was not willing to participate this time around.

The film's director, Peter Chelsom, discussed the filmmaking journey nearly two decades after the movie's release. In an interview with Insider in October 2021, Chelsom shared his perspective on creating a world that he hoped could exist. Despite the absence of a clock and the inability to see stars, he believed that these elements allowed for a more immersive experience, enabling viewers to escape. Chelsom emphasized the importance of the balance between the male and female protagonists, both of whom faced similar issues related to choosing a supposedly perfect partner and later realizing its impossibility. He criticized the romantic comedies of the early 2000s for their sexist portrayal of frat boys behaving badly, followed by them apologizing to beautiful blondes in the third act. Chelsom considered "Serendipity" to be the pinnacle of romantic comedies during that era.

Scroll below to see what the Serendipity cast has been up to since the 2001 holiday rom-com premiered:

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John Cusack

The character of Jonathan Trager in the movie Say Anything was brilliantly portrayed by the actor known for his notable roles in films such as Sixteen Candles, Stand By Me, True Colors, Bullets Over Broadway, Cradle Will Rock, High Fidelity, America’s Sweethearts, 2012, The Paperboy, Lee Daniels’ The Butler, Blood Money, and Utopia.

The Illinois native, whose sister is actress Joan Cusack, has previously been linked to Minnie Driver, Britney Spears and Neve Campbell throughout his lengthy Hollywood career.

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Kate Beckinsale

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Playing the role of Sara Thomas, Beckinsale portrayed the leading lady in the film. Since then, she has appeared in various film and TV projects, such as Much Ado About Nothing, Pearl Harbor, Laurel Canyon, Underworld, Van Helsing, The Aviator, Love & Friendship, The Only Living Boy in New York, The Widow, and Guilty Party.

Prior to her relationship with Pete Davidson in 2019, Beckinsale had previously dated Michael Sheen from 1992 to 2002, and they have a daughter named Lily together. She was also married to director Len Wiseman for 11 years before they split in November 2015.

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Jeremy Piven

Dean Kansky, Jonathan’s close friend, was portrayed by Piven. Besides his role in Entourage, he also appeared in popular films like Say Anything, Judgment Night, and Music From Another Room. In addition to that, Piven showcased his talent in TV shows such as The Larry Sanders Show and Ellen. He was also a part of movies like Old School, Chasing Liberty, Keeping Up with the Steins, Spy Kids 4-D: All the Time in the World, and American Night.

The Emmy winner has been linked to Kelly Brook, model Sophie Turner, January Jones, Dita Von Teese and Vanessa Marcil.

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Bridget Moynahan

Playing the role of Halley Buchanan, Jonathan's fiancée, Moynahan, a native of New York, appeared in several films including Coyote Ugly, Sex and the City, The Recruit, Six Degrees, Ramona and Beezus, John Wick, and Blue Bloods. She will also be reprising her character as Natasha, Big's ex-wife, in the Sex and the City revival titled And Just Like That, scheduled to premiere on HBO Max in December 2021.

Prior to their split in December 2006, Moynahan dated NFL star Tom Brady, with whom she has a son named Jack. In October 2015, she tied the knot with businessman Andrew Frankel.

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Eugene Levy

Levy played the role of a Bloomingdale’s salesman in the production, alongside his co-creation of Schitt’s Creek. In addition to his work on Schitt’s Creek, Levy has also appeared in Double Negative, SCTV, Splash, Father of the Bride, The Secret Life of Girls, American Pie, Bringing Down the House, New York Minute, Cheaper by the Dozen 2, Madea’s Witness Protection, Finding Dory, and Star-Crossed: The Film.

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The Canada native got married to Deborah Divine in 1977. They went on to have two children, son Dan Levy and daughter Sarah Levy. Eugene had the opportunity to work alongside both of his children on the Pop TV series, Schitt’s Creek.

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John Corbett

Content: The actor from West Virginia portrayed Sara's second romantic interest. Corbett has also acted in popular shows like Northern Exposure and films like My Big Fat Greek Wedding, Sex and the City, Raising Helen, Raise Your Voice, The Messengers, United States of Tara, Parenthood, Sex & Drugs & Rock & Roll, To All the Boys I've Loved Before, 47 Meters Down: Uncaged, and Rebel. In 2020, this actor, known for their role in And Just Like That, secretly married Bo Derek, their partner of almost two decades.

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Molly Shannon

Sara's BFF, Eve, was portrayed by the SNL alum. Following that role, she went on to star in various films including The Phantom of the Opera, Never Been Kissed, Wet Hot American Summer, American Splendor, The Music Man, My Boss's Daughter, Marie Antoinette, Talladega Nights: The Ballad of Ricky Bobby, Kath & Kim, Promising Young Woman, and The Other Two.

The Ohio native has been married to Fritz Chesnut since 2004, with whom she shares children Stella and Nolan.