Valentine’s Day is the perfect time to cozy up with a feel-good romantic comedy, but instead of revisiting the same old classics, why not explore some underrated gems? There are countless romantic comedies that have flown under the radar, underappreciated while offering something fresh and unique to fans of the genre. I’ve compiled a list of my ten favorite underrated romantic comedies that deserve a watch this Valentine’s Day!
10. About Time (2013)
Written and directed by rom-com legend Richard Curtis, About Time follows Tim, a young man who discovers that the men in his family have the ability to travel through time. Rather than using this gift for personal gain, Tim decides to focus on improving his love life, especially after meeting the charming Mary. Rachel McAdams and Domhnall Gleeson are so charming to watch together. Their love story shapes the film, but Gleeson’s scenes with Bill Nighy, who plays his father, are the true heart and soul of About Time. Their bond remains a constant in Tim’s life, from his early years through his marriage and the birth of his children. It’s hard to extinguish, even when suffering from loss. While About Time is labeled a romantic comedy, it’s so much more than a romance and so much more than a comedy. It’s an insightful, sentimental look at time and how often we take it for granted. Life is so fleeting that we need to appreciate what we have while we have it.
9. It Should Happen to You (1954)
It Should Happen to You stars Judy Holliday as Gladys Glover, a woman who dreams of being famous but feels overlooked by society. After a series of disappointments, Gladys rents a billboard in New York City with just her name on it, a move that unexpectedly catapults her into the public eye. Gladys’s obsession with fame threatens a blossoming romance with her down-to-earth neighbor, Pete, who questions her motivations. The movie cleverly critiques celebrity culture with the message that love and self-worth are far more fulfilling than fame. With Holliday’s endearing performance and the film’s witty dialogue, It Should Happen to You remains a delightful, if often overlooked, classic of the rom-com genre.
8. Plus One (2019)
Ben (Jack Quaid) and Alice (Maya Erskine) are two college friends who, despite their vastly different views on love, agree to be each other’s dates to a series of weddings they’ve been invited to over the summer. I admit that this has some heavy ‘When Harry Met Sally’ (1989) vibes, and it totally works. I’m a sucker for the friends-to-lovers trope, and Plus One gives it some edge by offering a deeper look into Ben and Alice’s relationship. The happily ever after that we tend to get at the end of most rom-coms is traded in for realism, including the messy, flawed complications of falling in love and trying to stay there. Plus One’s journey is endearing, with plenty of laughs and a love that feels incredibly authentic and real.
7. Sliding Doors (1998)
Gwyneth Paltrow stars as Helen, a woman whose life takes two distinct paths after a chance event—whether or not she catches her train—sets her on divergent journeys. One timeline follows her as she pursues a new relationship and her career, while the other shows the consequences of a missed connection and a broken heart. Sliding Doors is a unique exploration of fate, choice, and how the smallest decisions can radically alter our lives. This is a movie for all the people who can’t help but wonder “what if” and yet it’s also a cautionary tale that the grass isn’t always greener on the other side. I was obsessed with this movie in my teen years and it holds up surprisingly well. And who can resist the charm of ‘90s John Hannah?
6. Definitely, Maybe (2008)
Amid a relatively amicable divorce, a former political consultant, Will Hayes (Ryan Reynolds), agrees to tell his daughter Maya (Abigail Breslin) the truth about his past, his relationships, and how he met and fell in love with her mother. He changes the names of the three women with whom he had meaningful relationships, including his soon-to-be ex-wife, while Maya attempts to piece together the truth to discover which woman became her mother. This is Ryan Reynolds before he became Ryan Reynolds and he’s a charming leading man who shares insanely good chemistry with all three leading ladies. If you’re looking for some hardcore ‘90s nostalgia amid rom-com intrigue, Definitely, Maybe is the right rom-com for you.
5. Man Up (2015)
I will forever shout from the rooftops about this movie. Nancy is traveling to her parents’ 40th-anniversary celebration when she is mistaken for a blind date by a man named Jack. Shenanigans ensue! Man Up is a romantic comedy that certainly flew under the radar back in 2015, which is a damn shame. Simon Pegg and Lake Bell exude chemistry and the movie balances the romance and humor in a way that so many modern rom-coms fail to do. Man Up is endearing and edgy and remains one of my favorite hidden gems.
4. Fire Island (2022)
This modern take on Jane Austen’s Pride and Prejudice finds a group of friends spending the week together on Fire Island in New York, an annual tradition that may soon end. The story revolves around Noah (Joel Kim Booster), the heart of the group who is determined to help his best friend Howie (Bowen Yang) get laid. However, Howie is a romantic who wants to connect with someone before they have sex. So when he meets Charlie (James Scully), he’ll finally get to live his rom-com fantasy. I think it’s safe to say Fire Island is one of the best romantic comedies released in 2022. It has everything you would want in a rom-com – a clever, romantic script, hot boys, a killer soundtrack, and meaningful characters who feel real instead of the typical rom-com stereotype.
3. Long Shot (2019)
I feel like Long Shot should have been a much bigger hit than it was. Released in 2019, it seemed to come and go with very little fanfare. And that’s a shame. Seth Rogan plays Fred Flarsky, a journalist who reunites with his childhood babysitter – and crush – Charlotte, who is now the Secretary of State. When he becomes her speech writer, sparks fly! Long Shot has plenty of romance, but it also more than delivers on the comedy. The humor is both raunchy and clever, and Theron especially delivers a dedicated, comedic performance, going toe to toe with Rogan in every scene and often outshining him. There are some wonderful throwbacks to the ’90s, including a couple of nods to Pretty Woman, and even though the movie may follow the tried and true rom-com formula, Long Shot still feels fresh thanks to the edgy political commentary, the engaging humor, and fantastic performances from Rogan and Theron.
2. Only You (1994)
After playing with an Ouija board with her brother, Faith is convinced her destiny is with a man named Damon Bradley. This is reiterated later at a carnival where a fortune teller mentions the same name. Years later, Faith is engaged to be married but receives a call from a friend of her fiancé, who is about to board a plane for Italy, but tells her his name is Damon Bradley. Only You is an “old school” romantic comedy, where the premise is whimsical and far-fetched, but still oh, so romantic. It’s utterly devoid of the cynical, unlucky-in-love traits that plague a lot of rom-coms these days and pushes together two people who just want to believe that love is written in the stars. Perfect for a cozy Valentine’s Day.
1. Palm Springs (2020)
Palm Springs is a refreshing take on the time-loop genre, blending sci-fi elements with romantic comedy. Nyles (Andy Samberg) and Sarah (Cristin Milioti), are two wedding guests who find themselves trapped in a never-ending loop of the same day at a desert resort. After Sarah accidentally gets caught in the loop with Nyles, they begin to navigate their repeated experiences with a mix of humor, frustration, and existential reflection. Produced by The Lonely Island, you may assume Palm Springs is just 90 minutes of silliness, but the film is actually a thought-provoking watch, carried by strong performances and sharp dialogue. Palm Springs was released by Hulu in the middle of the pandemic so I don’t think it got the widespread recognition it deserved. But this is a romantic comedy for any film fan, even if you’re not a big fan of the genre itself.
Do you have any Valentine’s Day movie recommendations? Share them with us in the comments!
