Two Sex and the City Recurring Characters Get Duped Again in Serendipity

Rom Coms is a movie genre that I hate and love. Love for happy endings and hate for some horrible traits behind how they get together. Serendipity is one of many romantic comedies that I hate and love. Jonathan Trager (John Cusack) and Sara (Kate Beckinsale) reach for the same pair of black gloves in the New York department store and it was an initial great meet-cute. But we found out both were in relationships, and Jonathan forgot the gloves were for his girlfriend while having some sundaes with Sara at the Serendipity cafe—already a red flag. 

Re-watching Serendipity made me realize it wasn’t a movie on fate instead two people are playing games with each other and hurting the closest ones in their lives. Sara’s character assumes that fate doesn’t want them together when she gave her number to Jonathan and the wind blew it away. Then, she continues the fate train with selling Gabriel García Márquez's Love in the Time of Cholera book with her number, pressing the elevator to the 23th floor, and buying gum with his number on a five-dollar bill. Jonathan was interested in Sara, but she kept insisting fate will bring them back together with those items. 

A few years later, Jonathan and Sara are engaged to two different people—Halley and Lars. During the time of Jonathan and Halley’s wedding, more signs came up with Paul Newman’s Cool Hand Luke movie poster and Sara’s name mentioned by his hairstylist and a random cyclist. These supposed signs shouldn’t be taken as fate, but Jonathan getting cold-feet about the wedding while Sara’s not enthusiastic about her engagement. 

Jonathan and Sara confine these signs to their best friends, Dean (Jeremy Piven) and Eve (Molly Shannon), where they come from a realistic perspective with knowing that Halley and Lars care for them and marriage is work. Sara tricked Eve to fly to New York as a birthday present while Jonathan forces Dean to go around the city to track Sara down using the information they got from her receipt on the black gloves.

No one noticed their fiancés, Halley (Bridget Moynahan) and Lars (John Corbett), got cheated on Sex and the City by Mr. Big and Carrie Bradshaw—as Aidan and Natasha. Aidan was in a relationship with Carrie while Big married Natasha. Like their parallel characters in Sex and the City, Halley and Lars had no clue of Sara and Jonathan’s doubts. 

In Serendipity, I felt more emphatic towards Moynahan’s character because she’s invested more in the relationship—she even got Jonathan the Love in the Time of Cholera for his wedding gift knowing he looks at the book at stores and not purchasing it and Jonathan continues to chase Sara three days before their wedding. However, Lars followed Sara to New York, and he still focuses on his folk music career with the interrupted calls during the trip. I can’t help but wonder how much Halley and Jonathan’s wedding costs and Lars spent on Sara’s engagement ring. 

I think about how Sara and Jonathan’s relationship was a selfish act like Carrie and Mr. Big next to other romantic comedies’ ruined engagements and weddings. 


Katherine Abando is a lifestyle writer and her favorite romantic comedies are Hitch and Palm Springs. 

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Katherine Abando