Best Romantic Comedies to Watch on Valentine’s Day

The Princess Bride, Cary Elwes, Robin Wright

Valentine's Day is very nearly here. For some, that might mean a fancy dinner at an expensive steakhouse and swapping equally expensive personal gifts. For others, that might mean simply getting a nice takeout meal and some cheap wine and having a good time with your partner, no matter the cost.

For many, it likely entails watching a few lighthearted romantic comedy movies as a way to wrap up the special day.

There's really no end to the potential romantic comedy movies to watch on Valentine's Day when it comes down to it. Just look back to the days of Charlie Chaplin (City Light) or the Cary Grant screwball comedies of the 30s, and you’ll find that many (if not all) of them contained a comedic, romantic plotline of some kind.

Over the years, as you might've guessed, the number of rom-coms has only grown, taking on more unique premises to distinguish themselves from their contemporaries. Some incorporate elements of fantasy (The Princess Bride), some science fiction (Palm Springs). Some are raunchy (The 40-Year-Old Virgin), some are wholesome (You've Got Mail).

As different as these romantic comedy movies are, all of them remain immensely enjoyable,  making the perfect holiday viewing material this coming Valentine's Day. If you're thinking about spending some precious time with that special someone relaxing and watching a romantic movie, here are a few rom-coms we highly recommend.

1. When Harry Met Sally… (1989)

When Harry Met Sally
Image Credit: Columbia Pictures.

One of the most popular and critically acclaimed romantic comedies of all time, When Harry Met Sally… is a staple of the rom-com subgenre. It has an unconventional approach, an enjoyable premise, and plenty of comedy and emotion to entertain viewers throughout its relatively short runtime (it's only about an hour and a half).

When Harry Met Sally… tells the changing relationship between two fellow New Yorkers, Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan). Initially, the two meet on a long, cross-country trip from Chicago to New York shortly after college, though they part on less than amicable terms.

The film then jumps ahead several times over the course of Sally and Harry's lives, tracking their chance encounters as their feelings towards each other gradually change and become more romantic. Upon its release, When Harry Met Sally… won numerous positive reviews from critics, all of whom praised its unique, nonlinear approach to the romance genre, its comedic performances, and intelligent script from Nora Ephron.

It would earn several prestigious award nominations, including an Academy Award for Best Original Screenplay, and Golden Globe nominations for Best Motion Picture (Comedy or Musical), Best Director (Rob Reiner), Best Screenplay, Best Actor (Crystal), and Best Actress (Ryan).

2. The 40-Year-old Virgin (2005)

Scene from The Princess Bride
Image Credit: Universal Pictures/

If you're looking for a little less romantic and perhaps a little more on the funny side, you'd be hard-pressed to find a better rom-com than The 40-Year-Old Virgin. Andy (Steve Carrell) is a good-natured, mild-mannered 40-year-old working at an electronics store. When his coworkers (Paul Rudd, Seth Rogen, and Romany Malco) discover that he hasn't slept with a woman before, they try to help him lose his virginity.

Despite numerous false starts, Andy eventually meets a woman (Catherine Keener) with whom he develops a genuine emotional connection. However, his timidity and lack of experience threaten to undo their relationship.

The 40-Year-Old Virgin is essentially two movies in one. On the surface, it's a raunchy comedy that gave Carrell and director Judd Apatow their big break, boasting some hilarious scenes showcasing Andy's failed attempts to lose his virginity. On the flip side of the coin, it's a movie that focuses on an individual learning to accept who they are, the kind of person they want to be with, and overcoming their own insecurities for the sake of their relationship.

At the end of the day, if you truly meet someone you love and want to spend the rest of your life with, trivial matters like self-perceived flaws shouldn't matter. The right person will accept for who you are, regardless (as seen here).

3. Palm Springs (2020)

palm springs scaled
Image Credit: Hulu.

It feels weirdly sacrilegious to include Palm Springs on this list in place of Groundhog Day, especially considering Palm Springs is basically Groundhog Day with two people stuck in an infinite time loop instead of one.

However, it's for that very reason that Palm Springs earned a spot on this list, taking clever advantage of the time loop premise originated by Groundhog Day. When Sarah (Cristin Milioti) meets the mysterious Nyles (Andy Samberg) at her sister's wedding in Palm Springs, she is immediately charmed by his carefree attitude and laid-back personality.

After a strange encounter locks her into a permanent time loop with Nyles, with the same day repeating itself over and over again, they slowly begin to develop romantic feelings for one another as they try to escape. Palm Springs may be nearly identical in its general concept to Groundhog Dog. Still, its originality, relatable characters, and the performances from the main cast involved help set it apart despite the plot similarities.

Like Groundhog Day, Palm Springs would win extremely positive reviews from critics, earning Golden Globe nominations for Best Motion Picture (Musical or Comedy) and Best Actor (Samberg). It also won the Critics' Choice Award for Best Comedy.

4. His Girl Friday (1940)

His Girl Friday
Image Credit: Colombia Pictures.

When it comes to romantic comedies, sometimes it's worth going back to the beginning. From the mid-1930s until the 1940s, numerous romantic comedies were released, including several amazing screwball comedies that have aged phenomenally well (Bringing Up Baby, The Palm Beach Story, and The Awful Truth, among others).

A classic of the screwball genre, His Girl Friday tells the story of a no-nonsense newspaper editor, Walter Burns (Cary Grant), who's about to lose his best reporter and ex-wife, Hildy Johnson (Rosalind Russell), as she prepares to settle down and remarry. Pleading with her to take on one last assignment before she leaves, Burns tries everything he can to win Hildy back and keep her on at the newspaper.

Based on Ben Hecht's classic stage play, The Front Page, the genius of His Girl Friday was the decision to make Hildy (originally a man in the play) a woman, giving the story an element of romanticism and adding personal stakes for Burns instead of simply a professional desire to retain his best employee. Today, His Girl Friday is considered one of the best movies of its era and genre and contains Cary Grant's probably most famous role outside of his collaborations with Alfred Hitchcock.

Praised for its comedic elements, fast-paced story, and rapid-fire, overlapping dialogue (director Howard Hawks set out to break the record for the quickest dialogue delivery in film), it's a chaotic romp of a movie that never slows down.

5. Forgetting Sarah Marshall (2008)

forgetting sarah marshall 1
Image Credit: Universal Pictures.

So far, we've highlighted many movies about individuals meeting someone new in their lives and forging a romance with them. However, we haven't discussed in great detail the prospect of moving on with your life after failed romances and the idea of picking yourself up and looking for the truly right sort of person to spend your time with.

When Sarah (Kristen Bell) ends up breaking up unexpectedly with Peter (Jason Segel), he tries to take his mind off of it by vacationing at a Hawaiian resort, not realizing that Sarah and her new boyfriend, Aldous (Russell Brand), are staying there as well. While he initially avoids them at all costs, Peter eventually grows past the trauma of his breakup when he meets Rachel (Mila Kunis), a hotel employee with whom he becomes smitten.

There are really no two ways around it: break-ups absolutely suck. No matter how much preparation you have or how ready for the end you are, the heartache you feel losing someone you love always hurts.

However, as demonstrated in this movie, a breakup isn’t necessarily the end of the world, and in fact, you may even be better off for it in the end, making room in your life for the ideal partner who is truly perfect for you.

6. Amélie (2001)

Image Credit: Canal+.

One of the most original romantic comedy movies ever made, Amélie may also be one of the greatest French movies made in the last few decades. Set in the bustling Parisian district of Montmartre, Amélie (Audrey Tautou) is a young, shy waitress who decides to try and change others' lives for the better as a way to escape her own solitary lifestyle.

Eventually, she meets an eccentric young man (Mathieu Kassovitz) with whom she falls in love, though she struggles to overcome her quiet nature and express her feelings to him. Director Jean-Pierre Jeunet incorporates romantic elements into various genres you wouldn't altogether expect to feature romance (such as the love story at the center of his earlier, post-apocalyptic dark comedy, Delicatessen).

Here, Jeunet focuses on crafting an exclusively romantic story, depicting various Parisian residents who each have their own individual idiosyncrasies and fall in love with each other despite these quirks. (As seen in Amélie, we’re all different, and it’s the idea of accepting those differences that makes our love for one another so special and unique.)

As lighthearted in tone as the movie is, Amélie still has very moving emotional sequences as well, emphasizing the importance of how precious time is and how we should all spend doing things we truly care about with the people we love most.

7. You’ve Got Mail (1998)

Youve Got Mail scaled
Image Credit: Warner Bros.

As a general rule, pretty much any 1990s movie starring Tom Hanks opposite Meg Ryan is a romantic comedy worth seeing. Sleepless in Seattle is, of course, a classic; Joe Versus the Volcano is supremely underrated, but for our money, the best and likely most wholesome would be their final collaboration together, 1998's You've Got Mail.

Based on the Hungarian Parfumerie (which served as the inspiration for the classic Jimmy Stewart film, The Shop Around the Corner), Kathleen (Ryan) runs a small, independent bookstore in New York whose operations are threatened by an encroaching chain of competing bookstores.

To escape the frustrations of her personal and professional life, Kathleen regularly corresponds with an anonymous person in an online chatroom, not knowing the person is really her business rival, Joe (Hanks). It's always a delight to see two individuals with such chemistry as Hanks and Ryan in any movie, and here, their onscreen relationship couldn't be more perfect.

Like Ryan's on-screen relationship with Billy Crystal in When Harry Met Sally…, Ryan and Hanks can switch between mutual antagonism towards each other in one scene and seamlessly illustrate subtle signs of affection for one another in the next.

It's the performances that give this movie its charm, as well as the nostalgia of watching a movie from a simpler time (AKA the 90s, with its online chat rooms, independent bookstores, and AOL's “you've got mail” jingle).

8. The Princess Bride (1987)

Scene from The Princess Bride
Image Credit: 20th Century Fox.

Director Rob Reiner's other most-remembered and likely his most popular work is his 1987 cult classic, The Princess Bride, one of the most lighthearted, enjoyable, and romantic fantasy movies you'll ever see. Adapted from William Goldman's novel of the same name, Buttercup (Robin Wright) is a young woman betrothed to the power-hungry Prince Humperdinck (Chris Sarandon) in the fictional kingdom of Florin.

After three men with nefarious intentions kidnap her, Buttercup finds an unlikely savior in the form of a mysterious man in black (Cary Elwes) who goes to extreme lengths to rescue the young princess bride from harm. Looking at this list, it's hard to say whether everyone will enjoy something like When Harry Met Sally… or You've Got Mail. However, we can confidently say that pretty much everyone can enjoy a movie like The Princess Bride. It has action, romance, comedy, thrilling scenes involving terrifying, human-sized rats and shrieking eels, and even political intrigue.

Yet, despite it all, at its heart is perhaps the most feel-good story there is, built around Buttercup and her lover’s commitment to each other and the distances they go to protect one another from harm.

Additionally, the movie has perhaps the most iconic subplot of all time, featuring Mandy Patinkin's search for the six-fingered man who killed his father when he was a boy. (Even if you somehow haven't seen this film, virtually everyone knows his now-famous line: “Hello, my name is Inigo Montoya. You killed my father. Prepare to die.”)

9. The Big Sick (2017)

The Big Sick Movies on Amazon Prime
Image Credit: Prime Video.

Most of the movies detailed on this list do a fairly decent job portraying the ups and downs of a relationship. However, no movie better explores the complex emotions associated with romantic relationships than 2017's The Big Sick.

Loosely based on Emily V. Gordon and Kumail Nanjiani's past relationship, Kumail (Nanjiani) is an aspiring Pakistani comedian who meets the white psychology student, Emily (Zoe Kazan). They soon begin dating but agree to stop seeing one another due to their cultural differences. When Emily falls ill from a mysterious disease, Kumail decides to stay by her side, coming to terms with his own feelings towards her in the process.

The Big Sick earned incredibly positive reviews upon its release, with notable praise for its emotional script, performances, and ability to shift back and forth between light-hearted comedy to hard-hitting drama. Included on the AFI's top 10 movies of 2017, it would also earn an Oscar nomination for Best Original Screenplay.

As many of us likely know by now, love isn't always sunshine and rainbows. Often, it's our loyalty and commitment to each other even during the hardest times in our lives that illustrate our strong feelings for one another.

In the case of The Big Sick, you don't need to storm a castle or battle a dragon to win the heart of your beloved. Simply staying by their side and comforting them when things get difficult or uncertain is more than enough.

10. Something’s Gotta Give (2003)

somethings gotta give scaled
Image Credit: Warner Bros.

“It's never too late to find love” is essentially the main message behind 2003's romantic comedy, Something's Gotta Give, featuring the absolutely wonderful pairing of Hollywood heavyweights Jack Nicholson and Diane Keaton.

Harry Sanborn is a 60-year-old wealthy playboy record producer who exclusively dates women younger than him. After he and his current girlfriend (Amanda Peet) venture to the Hamptons to vacation at her mother's beach house, Harry meets and eventually falls for his girlfriend's mother, Erica (Diane Keaton), a 50-year-old successful playwright.

Something's Gotta Give is largely rooted in people's disappointment at being unable to find emotionally fulfilling relationships. To escape this heartache, both characters either invest in simple, superficial relationships that lead nowhere (in Harry's case) or focus exclusively on their work (in Erica's).

It's only when you stop and look around at the people in your life and actually acknowledge how you feel when you're around them that you begin to see how deeply you care for them. It's a simple, straightforward, but incredibly valuable lesson to learn at any stage in life, showing that even when you think it's too late to find true love, that special person you'd never thought you'd find could be waiting right around the corner.

Author: Richard Chachowski

Title: Journalist

Expertise: Classic Film, Contemporary Film and TV, Video Games, Comic Books


Richard Chachowski is an entertainment and travel writer who has written for such publications as Wealth of Geeks, Fangoria, Looper, Screen Rant, and MSN. He received a BA in Communication Studies and a BA in Journalism and Professional Writing from The College of New Jersey in 2021. He has been a professional writer since 2020. His geeky areas of interest include Star Wars, travel writing, horror, video games, comic books, literature, and animation.