New York is more than just a city - it is a symbol of the American Dream. People come to the sprawling metropolis from all corners of the world to seek new opportunities and find their version of success. Some seek fame, others fortune. The rest? They're looking for love in the Big Apple.
A considerable number of rom-coms on the market take place in New York City, and there's a good reason why. Besides its larger-than-life architecture (e.g., Grand Central Station, Times Square) and idyllic settings (e.g., Central Park, the top of the Empire State Building), the city is home to unique individuals coming from all walks of life.
In a city home to 8.3 million souls with different backgrounds, careers, and social statuses, there's an opportunity to explore complex romantic connections and create richer, more intimate stories. The result? A never-ending list of rom-coms set in New York City.
We've ranked the ten best rom-coms that take place in the City that Never Sleeps. Check out the list below.
10. New York, I Love You (2008)
New York, I Love You is an anthology film featuring ten short stories focusing on the romantic lives of different New Yorkers. From an aspiring artist searching for a muse, a wealthy guest curious about a mysterious bellhop, to a young high school prom date, the film showcases the diverse relationships you can expect in the city. Unlike movies like Love, Actually or New Year's Eve, the characters in each short don't intertwine. New York, I Love You features an ensemble cast with big names like Natalie Portman, Bradley Cooper, and Shia LaBeouf.
The movie is set in the city's five boroughs and is filmed in some of New York's iconic places, namely the Diamond District, Chinatown, Upper East Side, Central Park, the Village, and Tribeca. Each short film in this movie presents a portrait of New York City in its glorious authenticity. Since each short is only around 10 minutes in length, it can be pretty challenging to form an instant emotional connection with the characters as they're looking for love. But with ten directors, each with their distinct vision and idea of romance, you'll find this patchwork of a movie uniquely mesmerizing.
9. Set It Up (2018)
Set It Up takes on the classic matchmaking story arc with a modern twist. Two assistants, played by Zoey Deutch and Glen Powell, are highly overworked and underpaid, thanks to their overbearing bosses. Lucy Liu plays Kirsten Stevens, a former journalist and now demanding editor of an online sports publication. Meanwhile, Taye Diggs plays the insufferable venture capitalist Rick Otis. As a desperate means to get their bosses to go easier on them, the two assistants hatch a plan to set their bosses up with each other, hoping that some romance could soften their edges.
The film has an incredibly predictable plot, and more can be done in terms of character development. But we're not complaining. Set It Up is light-hearted and cheerful, meant to be enjoyed during casual date nights or a leisurely weekend afternoon. While it might not be super realistic, the movie gives a glimpse into New York's infamous workaholic culture and the eclectic individuals roaming amongst the city's tall skyscrapers. Even office people need some loving too once in a while.
8. Maid in Manhattan (2002)
In Maid in Manhattan. Jennifer Lopez plays Marisa Ventura, a hotel maid and single mother of her 10-year-old son, Ty (Tyler Posey). When her co-worker suggests that Marisa should try on their guest's $5,000 dress to know what it feels like to dress rich, she gets caught by high-profile politician and senatorial candidate Christopher "Chris" Marshall (Ralph Fiennes). Under the impression that Marisa is one of the hotel guests, he falls head over heels for her, not knowing that she is one of the hotel maids.
The film is a modern-day Cinderella story. We've seen the familiar rags-to-riches story arc repeat itself in different movies over the years, so plot-wise, it is very predictable. But what makes the film very New York City is its portrayal of a class divide. Even in real life, there is a significant distinction between the higher echelons and the working class. So while romances like the one in Maid in Manhattan are a mere fantasy to some, it's slightly gratifying to see that romance knows no boundaries, whether money or status.
7. Nick and Norah's Infinite Playlist (2008)
Nick and Norah's Infinite Playlist is the go-to rom-com if you want to see New York City after hours in all its chaotic, unhinged glory. The film stars Michael Cera as Nick, the straight bassist of his queercore band who was recently dumped by his unbelievably gorgeous now-ex-girlfriend Tris (Alexis Dziena). After performing with his band in New York City, Norah (Kat Dennings) asks him to pretend to be her boyfriend for five minutes, complete with a fake kiss. The two high school seniors then spend the rest of the wee hours searching for Norah's drunken best friend, all while trying to find their favorite band's secret show.
What makes this film charming is how it takes us through the streets of Manhattan and offers audiences a look into NYC's finest eccentricities (although some might be overly exaggerated for dramatic purposes). We're talking stripping nuns, sloppy make-out sessions in the back of a cab, and a man dressed up as Jesus smoking a cig. Plot-wise, the movie doesn't have the most substantial story arc. Instead, the film offers an atmosphere, a whiff of nostalgia that transports us to the once-exciting days of being a teenager. Nick and Norah's Infinite Playlist is a celebration of what it's like to be a young person looking for companionship in one of the most densely populated cities in the world.
6. Enchanted (2007)
I now banish thee to New York City! It sounds odd, but that's actually the baseline of Enchanted, a fairytale gone wrong when the lovely Princess Giselle (Amy Adams) is banished by the evil Queen Narissa (Susan Sarandon). Exiled from the magical and animated lands of her home, she is transported to the gritty streets of modern-day Manhattan. The confused princess, who's now found herself in a chaotic world, scrambles through the dirty streets in sheer panic. Shortly after, Robert Philip (Patrick Dempsey), a charmingly flawed divorce lawyer, stumbles upon her and reluctantly lends her a helping hand, leading to some real-world romance.
Enchanted is an entertaining choice for both kids and adults. It may have the pretext of Disney-esque princess movies, but in it are profound messages about the concept of "happily-ever-afters" and whether that truly exists or not. The film is also very well-known for its musical numbers, especially "That's How You Know" - a wholesome five-minute piece set in Central Park. While many scenes were filmed at Steiner Studios, the movie was also shot at Times Square, the Brooklyn Bridge, and The Paterno.
5. 13 Going on 30 (2004)
13 Going on 30 is a hilariously wholesome yet inspiring story of Jenna Rink (Jennifer Garner), a 13-year-old unpopular teen who tries hard to be part of the "it" crowd. After being humiliated by her classmates during her birthday party, Jenna recedes to her closet and wishes that she was 30 years old. Shortly after, Jenna suddenly wakes up as a stylish 30-year-old living in a Fifth Avenue apartment. With no memories of the past 17 years, Jenna must now navigate her new life as an editor of her favorite fashion magazine, Poise. The current life she has now is all glitter and sparkles, but as she finds out what kind of person she has become to her family and her best friend, Matt Flamhaff (Mark Ruffalo), Jenna reconsiders what she truly wants.
The film is highly praised for its whimsical humor accompanying its important message of self-empowerment. It takes inspiration from a sweet fantasy where a regular teenager wishes for a different life. However, when she has her wish granted, she realizes that it's not all it's cracked up to be. 13 Going on 30 gives you an inside scoop into New York's trademark (although highly dramatized) world of fashion, with Jenna working for Poise as a celebrated editor and getting herself into mishaps with rival magazine Sparkle.
4. You've Got Mail (1998)
Directed by Nora Ephron, You've Got Mail is a romantic comedy of errors starring Tom Hanks as Joe Fox and Meg Ryan as Kathleen Kelly. Fox is part of the Fox family that owns Fox Books, a popular chain of mega bookstores. Meanwhile, Kelly runs The Shop Around the Corner, a small independent bookstore. The two become business rivals as Kelly's store is threatened with closure to make room for one of Fox's bookstore franchises. However, it all changes when Kelly goes on an AOL chatroom under the name "Shopgirl" and forms an instant connection with "NY152", not realizing that "NY152" is Fox himself. Likewise, Fox has no idea that "Shopgirl" is Kelly and is fascinated by her online presence.
You've Got Mail is a cookie-cutter romance that takes advantage of the secret identity story arc. You can almost predict how the story will lead, but it is still a clever plot. Hanks and Ryan form a joyful and uptempo onscreen chemistry, ultimately leading to its sugar-coated ending. What's entertaining is how both of these characters interact offline and online. And it's also hilarious that Kelly continuously berates Fox and swoons about how much of a gentleman "NY152" is in front of him (at this point, Fox already discovers who "Shopgirl" is but decides to keep quiet). A bulk of its filming takes place in New York City's Upper West Side, so you have the chance to watch the city in all its hustle and bustle.
3. Serendipity (2001)
If it's meant to be, it's meant to be - or so they say. Serendipity (2001) is a film that brings a whole new meaning to the word. Starring John Cusack as Jonathan Trager and Kate Beckinsale as Sara Thomas, the two met as they were Christmas shopping for their respective lovers. Smitten by each other, Trager was curious to see if their connection could lead somewhere. Meanwhile, Thomas believes that love is only possible if it's destined to be. So the two decide to test fate by splitting up and seeing whether destiny will bring them back together as soulmates, even if they're engaged to other people.
This movie is one exhausting yet exhilarating trip. The word "serendipity" essentially means the occurrence of events by chance, and boy, were there a lot of serendipitous events in this movie! You'll find yourself growling in frustration during specific points of the film as the two of them are so close to meeting several times until fate decides to have the upper hand. It's a very classic Shakespearean confusion with its near-misses and the characters' unbelievable timing. Also, Serendipity works as a portrait of New York during the peak of the Christmas season, and also features some of its timeless spots, such as Bloomingdale's, the Waldorf Astoria, and of course, Serendipity 3, a charming little restaurant often featured in films like One Fine Day and Trust the Man.
2. Sleepless in Seattle (1993)
Another classic by Ephron, Sleepless in Seattle demonstrates her skillful expertise in the rom-com genre. The film features Tom Hanks playing Sam Baldwin, a widower who can't seem to escape the grief of his wife Maggie's (Carey Lowell) passing. Eighteen months later, Sam still has trouble getting over her death. On Christmas Eve, his son Jonah (Ross Malinger) phones in to a national radio talk show under Sam's name and talks about how perfect his marriage with Maggie was and how much he misses him. As it turns out, many women across the country sympathized with Sam's story. Among those is a Baltimore-based newspaper writer Annie Reed (Meg Ryan), who can't help but be captivated by Sam, despite being engaged to someone else.
Ephron had a masterful understanding of the human need for emotional connection and knew how to translate that into a beautiful piece of art. The movie shows that love is just as important as our basic needs, like water, air, or food. Without love, we are unable to function properly (e.g., Sam going through a concerningly long grieving process, Annie feeling like something is missing from her engagement). This emotional tone is further supported by the film's clever dialogue, talented cast, and the story's somber yet burning momentum. Despite the name, Sleeping in Seattle features one of the most romantic scenes set in the backdrop of New York City, where Sam, Annie, and Jonah finally meet on top of the Empire State Building, with the wind blowing their hair and a gorgeous view of the city at night.
1. When Harry Met Sally… (1989)
Can a man and a woman remain friends without sex getting in the way? This question of all ages finally gets its answer in the hit rom-com When Harry Met Sally…, a slow-burning rom-com masterpiece with a plot of over 12 years and three months. Sally Albright (Meg Ryan) shares a ride with Harry Burns (Billy Crystal) as they're heading from the University of Chicago to New York. Throughout the 18-hour trip, they both learn about each other, only to realize they have very differing views on friendships and love. The movie jumps forward to the numerous times they meet again in the future, as they continue to try and fail in their search for love until the pair realizes that what they have means something to both of them.
With its sharp writing, perfectly timed dialogue, and outstanding casting, When Harry Met Sally… has many priceless moments that make this movie incredibly memorable. The film feels less of a conventional rom-com with a straightforward plot and instead focuses more on how the characters navigate through love and life. Besides the famous car ride scene (e.g. the "men and women cannot be friends" conversation), there are also moments like Albright's elaborate order at the diner, and the heated argument at their best friends' wedding. A timeless classic, When Harry Met Sally… remains relevant even this decade.