The 2000s were a great time forromance movies. Well-known titles such asMamma Mia!,Love Actually,Pride & Prejudice, andThe Notebooksprang up at this time, and all became commercially successful at the worldwide box office while also being remembered fondly all these years later. Even smaller indie romances likeEternal Sunshine of the Spotless Mind,Juno, and(500) Days of Summerbroke out with mainstream audiences and are still fondly remembered.
However, not every romance film from the 2000s got the attention and recognition it deserved. Some failed to do well at the box office, others were treated unnecessarily harshly by critics, while others have been forgotten about as time has gone on. With Valentine’s Day on the horizon and love, once again, being in the air, here’s a look at the most underrated romance movies from the 2000s.
Update August 12, 2025: This article has been updated with even more great underrated romances from the 2000’s to check out for your Valentine’s Day viewing pleasure.
12Sidewalks of New York (2001)
Directed by, written by, and starringEdward Burns,Sidewalks of New Yorkis a romantic comedy-drama built around the notion of six degrees of separation. Featuring an ensemble cast that also includes Rosario Dawson, Brittany Murphy, Stanley Tucci, and Heather Graham, the film depicts the lives of six Manhattan residents whose lives intertwine in various different ways. Telling various different stories revolving around themes of love, romance, marriage, fidelity, and sex, the film acts as one big exploration of relationships and people’s desire to be in the right one. The whole movie was shot in just 17 days and cost an estimated $1 million to make.
What Makes It Underrated
Sidewalks of New Yorkgarnered generally mixed reviews from critics upon its release, and only earned around $3.5 million at the worldwide box office. As well as that, it’s not as though the film has gained any kind of traction in the years since its release. Which is a shame, because overall,Sidewalks of New Yorkis a creative and original look at modern love and sex. While it may not be as clever or insightful as it wants to be, the film is still a witty and humorous alternative rom-com that makes good use of its talented cast. Don’t listen to the reviews, this is a far better film than critics would have you believe.Rent on AppleTV+
11It’s Complicated (2009)
It’s Complicated
InIt’s Complicated, Meryl Streep plays Jane Adler, a bakery shop owner who begins an affair with her ex-husband, Jake (Alec Baldwin), ten years after their divorce. Things become even more complicated when Jane develops romantic feelings for her architect, Adam (Steve Martin). Zoe Kazan, Hunter Parrish, and Caitlin Fitzgerald play Jane and Jake’s mortified children, while the film’s supporting cast also includes Lake Bell, John Krasinski, Rita Wilson, and Mary Kay Place. Written and directed by Nancy Meyers,It’s Complicatedreceived mostly mixed reviews from critics but proved to be profitable at the box office.
WhileIt’s Complicatedmay be rather predictable (just like most rom-coms), its stellar cast and gag-heavy script means that there’s enough originality and screwball fun to make it more than worth a watch. Writer and director Nancy Meyers is on top form, delivering what is arguablyone of her best filmsto date. Meanwhile, Streep, Baldwin, and Martin look like they’re having the time of their lives, and each give hilarious and wonderfully charming performances. Furthermore, with a magnificent supporting cast and an upbeat score courtesy of Hans Zimmer,It’s Complicatedis a cheeky, carefree, and delightfully enjoyable rom-com that deserves more love.Stream on Starz
Related:The Best Movies About Finding Love in Old Age
10Serendipity (2001)
Serendipity
Serendipity is a romantic comedy that follows the chance meeting of two strangers who leave their future together up to fate. Years later, they are each engaged to others yet find themselves compelled to seek out one another, relying on signs and serendipitous moments to guide their paths. The film explores themes of destiny, love, and the impact of seemingly random encounters on life’s journey.
Few films from the 2000s are more romantic thanSerendipity. Directed by Peter Chelsom, the 2011 rom-com tells the story of Jonathan (John Cusack) and Sara (Kate Beckinsale), two people who meet by chance in New York City and decide to have dinner together. Curious to see whether it was fate that introduced them to one another and whether they are destined to be together, the pair decide to carry out little tests. When the signs show that they are not meant to be, they go their separate ways, only for fate to bring them back together once again. As well as Cusack and Beckinsale, the film also stars Molly Shannon, Jeremy Piven, and Eugene Levy, among others.
As the premise would suggest,Serendipityis contrived and more than just a little bit schmaltzy, but that’s exactly what rom-coms are supposed to be like. It’s also light, fun, and full of heart, making it perfect for background viewing. Moreover, its central theme of destiny and how much fate plays a part in our relationships, is intriguing and something that is beautifully explored in the film. On top of that, Cusack and Beckinsale are both incredibly likable and charming, and the script is filled with some great lines. On the whole,Serendipityis a sentimental and syrupy sweet love story that is far better than it has any right to be.Stream on Max
9A Lot Like Love (2005)
A Lot Like Love
2005 romantic comedy-dramaA Lot Like Lovecenters on the relationship between Oliver and Emily, who are played by Ashton Kutcher and Amanda Peet, respectively. After initially meeting on a flight from Los Angeles to New York, where they have a steamy encounter in the plane’s bathroom, the pair spend the day together before each going their own separate way. Over the years, however, they keep finding each other again and again but, unfortunately, the timing is never quite right. That is, until it is. The film was directed by Nigel Cole, whose other work includesCalendar Girlsand Made in Dagenham, while the movie’s supporting cast includes Kathryn Hahn, Kal Penn, and Taryn Manning.
A Lot Like Lovereceived a broadly mixed response from critics, who found that the film offered very little in the way of originality. Don’t let this put you off, however, because there’s a lot to like about this forgotten 00s romance movie. For a start, the chemistry between the two leads is electrifying. From the moment Kutcher and Peet appear onscreen together, as a viewer, you instantly buy into the idea that these two people share a big attraction, as well as a deep connection. Furthermore, the performances of both as individuals are fantastic, with Peet, particularly, givingone of best performances of her career. Throw in a catchy soundtrack, a great road trip sequence, some funny supporting characters, and an ending that will melt every viewer’s heart, and you have the recipe for a pleasing and poignant romance movie.Not Available to Stream
8Youth in Revolt (2009)
Youth in Revolt
Based on the novel of the same name by C.D. Payne, 2009’sYouth in Revoltstarts like many teenage romantic comedies: with a virgin guy (Michael Cera) liking a girl (Portia Doubleday) and hoping he will lose his virginity to her. But the movie becomes something much stranger and unique, and not only because the girl in question, Sheeni, has a boyfriend and lives in another state. But on top of that, Cera’s character, Nick, has an alter-ego with an absurd mustache, and both teenagers seem to be completely in their own world and totally unaffected by the adults around them. Jean Smart stars as Nick’s mother, Estelle, while Zach Galifianakis plays her younger boyfriend, Jerry. Steve Buscemi, Fred Willard, Justin Long, and Rooney Mara also star.
Youth in Revoltwas released at the time when Cera was a teenage lead character (he also didJuno, Nick, and Norah’s Infinite’s PlaylistandScott Pilgrim vs. the World), and there’s no denying thathe plays to typehere. However, that’s not necessarily a bad thing, and, in many ways, it’s kind of the point in this film. Additionally, Cera and Doubleday (who’s known mostly for their work onMr. Robot)have undeniable chemistry, and each gives charming and surprisingly layered performances. It’s a funny, quirky, and, at times, bonkers film that makes a nice departure from the standard romance movie formula. With lots of clever pieces of dialogue and some nifty direction by Miguel Arteta,Youth in Revoltis a wacky and smart romantic romp that’s easy to fall under the spell of.Stream on Pluto TV
7Imagine Me & You (2005)
Imagine Me & You
Directed by the man behindMamma Mia! Here We Go AgainandTicket to Paradise,Ol Parker,the 2005 rom-comImagine Me & You,tells the story of Rachel (Piper Perabo), who, while preparing for her wedding to Hector (Matthew Goode), falls in love with the florist, a woman named Luce (Lena Headey). While she has feelings for this woman she just met, she still gets married, and things start to get complicated for all three people involved. The film’s mostly British supporting cast consists of Anthony Head, Celia Imrie, Sharon Horgan, and Darren Boyd, among others. It only managed to make $2.6 million at the box office and garnered mostly mixed reviews.
There’s a certain British flavor toImagine Me & Youthat makes itreminiscent of other films in the genre, such asFour Weddings and a Funeral,Love Actually, andBend It Like Beckham.And, while its true that the film might not quite be able to compete with those, better known, rom-coms, it definitely deserves more recognition than what it’s got. Falling in love when you’re already in a relationship is complicated, and even more so if it’s the first time you fall for someone of your same sex. Both the script and the performances of the cast do a great job at conveying the mix of emotions involved in such a situation, and the film as a whole handles its subject matter with nuance and pathos.Imagine Me & Youis a sharp and hilarious noughties rom-com that offers something unique from other films of the era. Unfortunately, it remains a crowd-pleaser lacking a crowd.Rent on AppleTV+
Related:20 Underrated British Romance Movies
6My Blueberry Nights (2007)
My Blueberry Nightsis about a woman named Elizabeth (singer Norah Jones, in her first acting role) who travels across America, encountering all kinds of people and their vision of love. The film was Wong Kar-Wai’s first American feature, and is an adaptation of his own Chinese-language short film,In the Mood for Love 2001.Jude Law, Natalie Portman, Rachel Weisz, and David Strathairn portray some of the characters Elizabeth encounters on her journey, and the film, overall, was met with mixed reviews from critics.
In terms of structure,My Blueberry Nightsis far from a conventional romance film. It employs a picaresque story style that essentially sees its main character meandering from one encounter to another, with not much of a plot holding it all together. For many viewers, this could certainly be off-putting, but those who can buy into the movie’s unorthodox nature will find it a highly rewarding watch. It has a bucolic, poetic quality to it, showing how each of the characters perceives love and how their experiences in love, both good and bad, mark their point of view. With committed performances by the cast and some interesting direction,My Blueberry Nightsis a hidden gem of a romance movie that is long overdue for reevaluation.Stream on Hoopla
5Zack and Miri Make a Porno (2008)
Zack and Miri Make a Porno
From acclaimed cult icon Kevin Smith,Zack and Miri Make a Pornowas his biggest attempt at making a mainstream comedy, separated from the continuity of his other films likeClerks,Mallrats, andJay & Silent Bob Strike Back. Seth Rogen and Elizabeth Banks star as the titular Zack and Miri, respectively, two high school friends who, after they fall behind on their bills, decide to make a porno to raise money. They recruit a color cast of characters to make their movie, all while realizing they also have feelings for each other.
Zack and Miri Make a Pornogot a big promotional push in the press, partially due to the risque nature of the title and Seth Rogen having become the biggest comedy star in the world with hits like Knocked Up and Superbad the year prior, but sadly the film was as box office disappointment. Domestically, it grossed $31 million, more than its $24 million budget, and many expected the movie to be a bigger hit. Now, it is sadly forgotten about, which is a shame because despite what appears to be a vulgar subject matter, it is actually a sweet, touching romance. It combines great laugh-out-loud gags with genuine tenderness that makes it an unconventional romance. It might have been a movie released too early or one that was never going to have mainstream appeal, but it is certainly one of the most underrated romances that does not get enough credit.Stream on Tubi.
4Kissing Jessica Stein (2001)
The 2001 indie rom-comKissing Jessica Steinis among one ofthe best LGBTQ+ movies of the 2000s. Directed by Charles Herman-Wurmfeld and written by its two main stars, Jennifer Westfeldt, and Heather Juergensen, the film follows Jessica (Westfeldt), a woman feeling pressured to find a man and settle down, who instead starts to fall for a woman named Helen (Juergensen).Kissing Jessica Steinwas made on a budget of just $1 million and went on to make $10 million at the worldwide box office.
In the last decade or so, LGBTQ+ romantic comedies have become more and more popular, but back in 2001, when the film was released, they were largely non-existent. In many ways, then,Kissing Jessica Steinshould be regarded as a ground-breaking film that was ahead of its time.In fact, the movie’s approach to sexual fluidity is far more progressive than most other romance films of the era and, even better, is that it deals with its subject matter in a real, honest, and funny way. Bolstered by a sharp script and a pair of charismatic performances from the two leads,Kissing Jessica Steinis a sweet, rich, forward-thinking romantic comedy worthy of greater recognition.Rent on AppleTV+
3Definitely, Maybe (2008)
Definitely, Maybe
Definitely, Maybeis aHow I Met Your Motherkind of story in that it revolves around single father Will (Ryan Reynolds) telling his10-year-old daughter Maya(Abigail Breslin) all about his three most important relationships while she (and the audience) try to guess who of those three women (played by Rachel Weisz, Isla Fisher, and Elizabeth Banks) is her mother. Most of the film is told through flashbacks, while fun metaphors are used to avoid talking directly about sex. It was written and directed by Adam Brooks, whose other film credits includeWimbledonandBridget Jones: The Edge of Reason.
Despite featuring an all-star cast, having a broad appeal, and receiving generally positive reviews from critics,Definitely, Maybeonly managed to make $56 million at the worldwide box office. Which is unfortunate given that far worse films haven’t earned a lot more. The movie is the definition of feel-good: it’s light, fun, witty, and leaves you feeling all gooey inside. Even though some elements of the film’s script have been done before, the movie as a whole feels surprisingly refreshing and delightfully creative. Additionally, with a talented ensemble cast, all of whom fit their roles perfectly, and some clever editing and direction,Definitely, Maybeis an endearing and breezy romantic comedy with a wonderfully unique structure that has been overlooked for too long.Stream on Max
