Picking a movie everyone will enjoy is usually hard, but it can be particularly difficult on Valentine’s Day.
It’s tough to find good movies these days, as so many of them are overly sentimental or just plain cheesy.
Luckily, many romantic movies avoid being overly sentimental or cheesy, offering humor and appeal without being sickeningly sweet.
Looking for something that fits the bill, but don’t know where to start? Here are 14 different options to consider.
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1. What If
Okay, so picture this: Daniel Radcliffe, ditching the wizarding world for a surprisingly sweet romantic comedy. He plays Wallace, a guy completely smitten with Chantry, played by Zoe Kazan. The catch? She’s already seeing someone else. It’s a familiar story – Wallace is stuck desperately trying to escape the friend zone, and honestly, it’s a really charming watch. It’s not groundbreaking, but it’s definitely enjoyable.
This movie is charming and funny, and Adam Driver delivers the lines at a rapid pace. It’s so engaging, you won’t even notice any potential discomfort.
RT review
A star rating of 3 out of 5.
Daniel Radcliffe stars in a charming, low-budget romantic comedy that tries a little too hard to be smart. But his character is the opposite – he’s a former medical student who’s given up on love after a painful split.
He finds comfort in his friendship with a cartoon animator, played by Zoe Kazan (known for her quirky roles, and visually enhanced by animated doodles). However, it’s obvious he’s hoping for something more. The main challenge to this is Kazan’s boyfriend, played by Rafe Spall, who provides some of the film’s biggest laughs.
Director Michael Dowse (known for Goon) primarily uses the clever back-and-forth dialogue between the main actors to maintain the film’s fast pace, even though the plot itself is fairly predictable. While Daniel Radcliffe isn’t quite as natural with the comedic, fast-talking style as his co-star, he cleverly leans into his own British awkwardness, similar to Hugh Grant. Surprisingly, the actors have a stronger connection when they aren’t trying to romance each other. – Stella Papamichael
Where to watch: Available to rent/buy
2. (500) Days of Summer
Okay, so for Valentine’s Day, if you’re like me and sometimes prefer a little bittersweetness, you have to watch this movie! It’s about Tom, played by Joseph Gordon-Levitt, who’s a total romantic and writes greeting cards. He’s completely blindsided when his girlfriend unexpectedly breaks up with him. Zooey Deschanel is amazing in it too – it’s just a really relatable and charming story.
He spent just over an hour trying to understand what went wrong in the relationship, and also considered if there was more to life than just being in love.
RT review
A star rating of 3 out of 5.
Marc Webb’s first feature film is a lighthearted romantic comedy. Joseph Gordon-Levitt, known from the TV show Third Rock from the Sun, plays Tom, an aspiring architect who writes greeting cards. He begins a somewhat unpredictable relationship with Summer (Zooey Deschanel), who starts as his boss’s assistant.
The movie tells the story of Tom’s 500-day obsession with Summer, constantly shifting between different points in time. Summer, however, doesn’t believe in love, which complicates things. Joseph Gordon-Levitt gives a wonderfully sweet and lovestruck performance that’s both funny and genuinely sad, perfectly capturing the confusion of being in love.
While Webb’s unique approach is often creative, it sometimes feels fragmented, like a series of disconnected short films. Exploring a relationship at various moments is a compelling idea, but the film’s uneven pacing ultimately makes it feel overly precious and slight.
Where to watch: Disney+
3. Nick and Norah’s Infinite Play List
This charming movie, inspired by the novel by Rachel Cohn and David Levithan, centers on two teenagers, Nick and Norah. They meet when Norah impulsively asks Nick to pretend to be her boyfriend, and they end up spending the night together trying to find a secret concert and locate Norah’s friend who’s had a bit too much to drink.
The atmosphere is lovely – there’s moonlight, music, and a touch of enchantment, but it’s all very mild and won’t overwhelm you.
RT review
A star rating of 3 out of 5.
In New York City one memorable night, Nick, a straight bassist in a gay boy band, unexpectedly meets Nora, a unique high school student who is babysitting her very intoxicated friend, Caroline.
Three friends are on a chaotic mission to find the location of a secret concert by the band Where’s Fluffy. Along the way, they face a string of mishaps: Nick develops a crush on Nora, Caroline disappears after fainting, and Nick’s ex-girlfriend does everything she can to sabotage their budding relationship.
This movie feels more inspired by After Hours than Superbad. While it tries to be a clever take on the typical teen comedy, it doesn’t quite capture the special spark it needs. It mostly relies on the appealing dynamic between its main characters, a supportive cast that includes LGBTQ+ individuals, and references to bands like Vampire Weekend and Band of Horses. – Jamie Russell
Where to watch: Available to buy from Sky Store
4. Easy A
Emma Stone shines in this funny and charming movie, which also has a sweet romantic side. She plays Olive, an ordinary high school student who creates a rumor about losing her virginity to make her life more interesting. But the lie quickly gets out of control.
It’s not too soppy, never floppy, and jam-packed with references to your favourite 80s teen movies.
RT review
A star rating of 4 out of 5.
Emma Stone shines in this high school comedy, playing a typically overlooked student. When rumors about her supposed love life begin to spread, she’s surprisingly pleased with the sudden attention.
We all know those stories will only lead to more problems for her. What follows is a clever, funny, and understanding story about the challenges of being a teenager. It confidently brings up both Nathaniel Hawthorne’s The Scarlet Letter and classic 1980s teen movies, and it manages to do so successfully.
The film also boasts a fantastic supporting cast, including Stanley Tucci and Patricia Clarkson as the protagonist’s cool parents, and Malcolm McDowell and Lisa Kudrow as school staff. They all deliver Bert V. Royal’s exceptionally well-written dialogue brilliantly. While the plot gets a little ambitious at times, the movie is consistently hilarious and appeals to audiences of all ages. – Trevor Johnston
Where to watch: Available to rent or buy
5. 10 Things I Hate about You
This funny teen movie, featuring Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, and Larisa Oleynik, is a fresh take on Shakespeare’s classic play, The Taming of the Shrew. It centers on Patrick Verona (Ledger) trying to win over the tough-to-impress Kat Stratford (Stiles).
You know how movies can either totally blow you away or just leave you cold? Well, this one definitely falls into the ‘blow you away’ category. I walked out feeling genuinely impressed – it’s a film that delivers and then some. Forget being underwhelmed, this is one you won’t soon forget!
RT review
A star rating of 4 out of 5.
This fun and charming romantic comedy reimagines Shakespeare’s The Taming of the Shrew in a modern American high school setting, marking the directorial debut of Gil Junger. The story centers on Kat (Julia Stiles), a rebellious and withdrawn teenager who avoids connecting with others.
This creates a challenge for Bianca, her younger sister who’s eager to start dating. Their father has decreed that Bianca isn’t allowed to date anyone until Kat does.
Heath Ledger first gained attention in Hollywood with his role in 10 Things I Hate About You, a movie filled with attractive young actors. Joseph Gordon-Levitt also appears as a kind, but shy, character who is interested in one of the leads. The film is well-timed, entertaining, and appeals to both teens and adults. – Joanna Berry
Where to watch: Disney+
6. High Fidelity
John Cusack consistently delivers performances that blend heartwarming romance with relatable sadness. In “High Fidelity,” he plays Rob, a somewhat withdrawn record store owner who reflects on his five most significant breakups, including one that’s currently happening.
Stephen Frears’ charming and upbeat film is a delightful pick-me-up that might just boost the confidence of anyone feeling a little down.
RT review
A star rating of 4 out of 5.
It’s okay that Stephen Frears moved the setting of Nick Hornby’s book from north London to Chicago. This funny, well-written movie, filled with familiar faces, is good all on its own.
John Cusack plays the owner of a struggling record store who’s dealing with a breakup. He’s both aware of his own flaws and strangely convinced he’s doing the right thing as he tries to win back his ex-girlfriend, who’s now involved with their neighbor, by pursuing a relationship with a singer.
John Cusack, and the film itself, truly shine when he’s speaking directly to the audience or making those “top five” lists with his co-stars, Jack Black and Todd Louiso. – David Parkinson
Where to watch: Disney+
7. Forgetting Sarah Marshall
Forgetting Sarah Marshall is a surprisingly sweet romantic comedy about heartbreak. Jason Segel plays Peter, who travels to Hawaii after a painful breakup with his famous girlfriend, Sarah. He hopes to move on, and finds a connection with a local hotel worker (Mila Kunis). However, things get tricky when Sarah arrives with her new boyfriend (Russell Brand).
It’s outrageous, a bit rough around the edges, and genuinely hilarious – thankfully, it avoids the overly sentimental and cloying tropes of typical romantic comedies.
RT review
A star rating of 3 out of 5.
The creators of popular comedies like The 40 Year Old Virgin and Knocked Up bring you this funny and unconventional romantic comedy. When musician Peter (Jason Segel) gets dumped by his famous girlfriend, Sarah (Kristen Bell), he heads to Hawaii hoping to mend his broken heart.
When Peter gets to the resort, he’s surprised to find Sarah and her new boyfriend, British rock star Russell Brand, are staying there too – actually, in the same hotel! The three main actors are all charming and perfectly suited for their roles, and the Hawaiian landscapes are beautiful.
Similar to other films by producer Judd Apatow, this one feels a little too long, with some scenes included that don’t really need to be there. However, it makes up for this with genuinely hilarious moments and a wide-ranging humor that consistently delivers big laughs. – Dave Aldridge
Where to watch: Available to rent or buy
8. When Harry Met Sally
Can men and women truly be just friends? That’s the central question explored in the classic romantic comedy starring Meg Ryan and Billy Crystal. The film, directed by Nora Ephron, beautifully portrays their decades-long attempt to maintain a platonic relationship.
RT review
A star rating of 5 out of 5.
This romantic comedy follows two college friends over about ten years, exploring their evolving relationship through life’s ups and downs and romantic entanglements. It playfully asks whether men and women can truly be just friends, or if sex always complicates things.
Meg Ryan and Billy Crystal have fantastic chemistry, and the supporting cast, including Carrie Fisher and Bruno Kirby, are excellent, bringing a bit of playful attitude to the film. Set against the backdrop of glamorous New York City and featuring a charming soundtrack, the movie feels like a stylish take on the kind of story Woody Allen might tell. Ultimately, it’s a wonderfully entertaining and thoroughly enjoyable escape.
While the memorable deli scene helped launch Ryan’s career, Nora Ephron’s brilliant script and Rob Reiner’s skillful direction offer many other enjoyable moments in this Oscar-nominated film. – Robyn Karney
Where to watch: MGM+
9. The Princess Bride
If you haven’t seen the 80s favorite, The Princess Bride, you’re in for a treat! Based on the popular book, it’s a hilarious and clever story about a farmhand named Westley and the princess he loves, Buttercup, as they find themselves in one crazy situation after another.
Mandy Patinkin’s brilliant Inigo Montoya makes every single soppy kiss worth it.
RT review
A star rating of 4 out of 5.
Rob Reiner consistently worked to avoid being pigeonholed as a director. After the heartwarming success of Stand by Me, he chose to make this unusual, yet ultimately delightful, story.
Okay, so the movie starts with Peter Falk telling the story to Fred Savage – you might recognize him as the kid from ‘The Wonder Years’ – and that setup actually creates this really cool, slightly detached feeling that runs throughout the whole film. It’s got all the classic fairytale stuff – monsters, giants, sword fights – which keeps the kids happy, but director Rob Reiner also sneaks in a ton of clever humor that goes right over their heads and keeps us adults chuckling. It’s a perfect balance, really.
The show’s success is mainly due to a wonderfully diverse group of performers, featuring Mandy Patinkin, Wallace Shawn, Billy Crystal, Christopher Guest from ‘This Is Spinal Tap,’ and the comedic duo of Mel Smith and Peter Cook. It’s a surprisingly enjoyable experience for the whole family. – John Ferguson
Where to watch: Tubi
10. Silver Linings Playbook
This film blends drama and comedy, and its Oscar wins make it worth checking out. Bradley Cooper and Jennifer Lawrence – who became a major star thanks to this role – play two people struggling with their own issues who find an unexpected connection through a dance competition. It’s a solid drama at its core.
Not so much dirty as flirty dancing, it’s a slick little flick that any girl or boy can enjoy.
RT review
A star rating of 4 out of 5.
This charming and unusual love story comes from director David O. Russell (known for films like The Fighter and American Hustle), and is based on the first novel by Matthew Quick. Bradley Cooper delivers a standout performance as Pat, a man with bipolar disorder who returns home to his vibrant, close-knit family in the Philadelphia suburbs after spending time in a mental health facility.
After unexpectedly meeting, he teams up with Jennifer Lawrence’s character, Tiffany – a wonderfully portrayed woman also struggling with her own issues – to intensely train for a dance competition, hoping it will be a healing experience for them both.
A side plot about increasingly risky bets on the Philadelphia Eagles, fueled by the father of the main character (played by Robert De Niro in a surprisingly strong performance), builds tension towards a climactic ballroom dance competition. This finale is more unexpected than a typical Hollywood ending, even though it still hits some familiar beats.
This romance is both unique and touching, and features excellent dance sequences. – Andrew Collins
Where to watch: Available to rent or buy
11. Before Sunrise
Richard Linklater’s Before trilogy, with Ethan Hawke and Julie Delpy, is consistently enjoyable to watch all the way through, but the first film is the most straightforwardly romantic of the three.
In this charming film, an American man named Ethan and a French woman named Celine meet on a train and share a memorable evening together in Vienna, quickly discovering a strong connection. It’s full of wonderful, unforgettable scenes.
RT review
A star rating of 4 out of 5.
In Richard Linklater’s captivating film, American traveler Ethan Hawke and French student Julie Delpy share a memorable night together in Vienna, sparking a powerful connection.
After gaining recognition with Dazed and Confused, Linklater establishes himself as a gifted filmmaker with this film. It’s a fresh, funny, and heartwarming romance that feels both current and classic, enhanced by beautiful scenes of Vienna and a clever script.
Ethan Hawke and Julie Delpy have fantastic chemistry in this charming and modern story of a brief connection, making it a truly successful film. – Alan Jones
Where to watch: Available to rent or buy
12. Bringing Up Baby
As a total rom-com fanatic, I always feel like you have to include the classics, and that means diving into those amazing screwball comedies from Hollywood’s golden age. There are so many great ones – The Philadelphia Story and It Happened One Night are always solid choices – but if I want something truly wild and hilarious, Howard Hawks’ 1938 film is just unbeatable.
Katharine Hepburn and Cary Grant have incredible chemistry in this delightful film, packed with hilarious moments – think escaped leopards and crashing dinosaur bones! It’s pure fun from beginning to end.
RT Review
A star rating of 5 out of 5.
Though it wasn’t a hit when it first came out, this clever comedy is now considered a classic of the screwball genre. Cary Grant charmingly plays against his usual persona as a quiet scientist, and Katharine Hepburn is fantastic as a bubbly, eccentric heiress. Her new pet leopard unexpectedly sparks a series of hilarious situations and, of course, a blossoming romance.
Katharine Hepburn brings a surprising warmth to her role, falling quickly for Cary Grant even as she attempts to disrupt his engagement. Director Howard Hawks keeps the film moving at a lively pace, smoothly guiding viewers through each comedic scene. – Calum Baker
Where to watch: BBC iPlayer
13. The Apartment
This beloved classic, directed by Billy Wilder, is often considered the greatest romantic comedy ever made by Hollywood. Featuring Jack Lemmon, Shirley MacLaine, and Fred McMurray, the film remains powerfully moving even 65 years after its initial release.
RT Review
A star rating of 5 out of 5.
Billy Wilder’s beloved film features Jack Lemmon as CC Baxter, a downtrodden insurance employee who lets his bosses use his apartment for affairs. He hopes to get promoted in return, but the promotions never materialize, making Baxter a truly pathetic figure.
Wilder skillfully downplays the story’s more serious elements, presenting the film as a charming romantic comedy. Jack Lemmon’s talented performance immediately makes us care about his character, and he finds redemption when he helps Shirley MacLaine’s character, an elevator operator having an affair with her dishonest boss, Fred MacMurray, during a difficult situation.
Despite dealing with potentially controversial themes, Billy Wilder and IAL Diamond crafted a timeless and award-winning love story. The film earned five Academy Awards, including Best Picture, Best Director, and Best Screenplay, as noted by Andrew Collins.
Where to watch: MGM+
14. The Worst Person in the World
This film, the third in Joachim Trier’s interconnected Oslo series, is a beautifully crafted romantic drama with a touch of sadness. While it’s primarily a moving story, it also includes enough humor and lighter scenes to keep things balanced.
Renate Reinsve, the acclaimed actress now nominated for an Oscar, gives a fantastic performance in this delightful film. It cleverly avoids common romantic comedy clichés and features some wonderfully creative scenes, making it a truly memorable and instant classic.
RT Review
A star rating of 5 out of 5.
If you’ve ever felt like time is slipping away, Joachim Trier’s beautiful and moving film will deeply resonate with you. Set in Oslo, it follows Julie (played brilliantly by Renate Reinsve) throughout her twenties as she navigates the uncertainties of life and love, told in twelve distinct chapters.
Julie often makes choices that would typically make her seem like the bad guy, but thanks to Renate Reinsve’s charming and relatable performance, she’s surprisingly sympathetic and doesn’t fit the film’s cynical label.
Director and co-writer Trier brings a lively and playful energy to the film, showcasing moments ranging from sweetly romantic kisses to a surprisingly psychedelic dinner party. It’s a unique movie that doesn’t fit neatly into any single genre, blending elements of romantic comedy and coming-of-age stories, and culminating in a deeply moving and impactful final act. – Max Copeman
Where to watch: Mubi
Authors
Patrick Cremona writes about movies for TopMob, covering new releases in theaters and on streaming services. He’s been with the site since October 2019, and during that time has interviewed many famous actors and reviewed films of all types.
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