Written by: Marc Klein
Starring: John Cusack, Kate Beckinsale, Molly Shannon, Jeremy Piven, Bridget Moynahan
Rating: [2/5]
Signs and omens create this belief of something larger navigating our lives almost like a higher being or universe trying to tell us something. Pretty much everyone has encountered some level of this idea where they see something and they believe it means something for their lives, but the extremes it takes in Serendipity to the point of meanness allows for a romantic comedy with all of the makings for something great resort to some middling fare.
After reaching for the same pair of gloves at Bloomingdales, Sara (Kate Beckinsale) and Jonathan (John Cusack) spend an evening getting to know each other and striking up a connection, unlike anything they have experienced before. With Sara believing in the idea of serendipity she sets the table for them being meant to be if some extremely set of circumstances take place.
The level of ridiculousness this feature has to offer comes in at quite a high level considering the events that need to occur in order for this romance to blossom. While yes it makes for some hilarious hijinks in the process, the area where Serendipity loses its way comes from crafting protagonists worth caring for and a circumstance where they become the least interesting characters within the story. This mostly occurs with John Cusack’s Jonathan. He falls head over heels for Sara in their initial interaction, which would be cute if he already did not have a girlfriend, which makes his particular desperation to get with Sara that very night awfully suspicious and it only gets worse later in the film when the man’s engaged and continues these shenanigans. At the very least Sara believe in the mysticism of serendipity and what it means. Jonathan is simply looking for a way to cheat on his poor fiancee Halley (Bridget Monahan).
As a result, the film becomes just a big disrespect of Halley and how she does nothing wrong that we see except love this guy, but she’s not the one meant to be with him because he wants to continually chase after Sara and cannot ignore the signs set before him. Everything feels genuine with the other characters but none of it does for Jonathan leaving for more than one judgemental glance at him throughout the film.
One area where the film certainly shines comes from the way it captures the magic of New York City during the Christmas season even if not all scenes were shot in the metropole. There’s simply nothing like it when the slightest bit of snow falls with the city as the backdrop. Even the classic look of a department store like Bloomingdales during the season brings this air of comfort of something special, which evidently sets off Sara and Jonathan on this journey of destiny where they cannot avoid each other.
On a philosophical level, this feature gets at an interesting idea at its core where if these two were meant to be then even the most unlikely scenario would occur to bring them together. It gets to the point in the movie where Sara asks Jonathan to write his name and number on five dollar bill, spends it, and states if they are meant to be she will miraculously get it back through another transaction. If not for the title of this movie and the character Sara proves to be that sounds like a classic line of how to get a guy to leave you alone due to the sheer unlikelihood of getting that exact same bill back. It allows for this sense of destiny of something as wholly unlikely to occur in order to justify all of the actions of these characters in the name of something larger than themselves pulling them together. Something that could be deemed as romantic but just comes off silly throughout the film, especially as it ventures on with its plot.
However, something about the film stops me from wholly disliking it and when distilling it all down it solely comes down to Kate Beckinsale. Her performance as Sara comes with this level of earnestness that while questioning her decision-making it leaves no doubt that she believes in the nonsense she does wholeheartedly. Something worth admiring even if skeptically and it allows us to turn off cynicism and go on this ride for her; it’s just a shame the other half of this tale does nothing to support it.
Serendipity certainly draws you in with its concept and idea but struggles to fully deliver something worthwhile and characters who draw you into this fantasy. We would have been better off with Sara having this romance with Eugene Levy’s salesman character who was insistent on respecting the counter. I say this in jest but it would have made for a more interesting film than what we received here.
Films with Josh 
