Valentine’s Day is the time of year that stirs up an assortment of emotions. And like a box of chocolates, you’re never quite sure what the holiday will bring. If you’re coupled, it may be time to spend beyond your means on an extravagant gift you hope will be appreciated. If you’re single, it may be time to ignore the commercialism and be thankful you are alone. Maybe it’s finally time to declare your affection to that person you hope will accept it, or time to assess why your last relationship failed. Time to either celebrate or curse the gods of love. Whether you are spending this weekend by your happy self, with your supportive friends, or caked up with your boo, it’s always the right time for a double feature. Here are a few not-so-obvious movie pairings to add to your Valentine’s Day watchlist.
1. Generations of Excellence: The Pullmans
While You Were Sleeping (1995)
The elder, Bill Pullman, is simply charming in this modern-day rom-com classic starring himself and Sandra Bullock as the couple that we need to get together. But upon the first table read, the script was not up to standards for anyone, and Bill wanted to quit the film. Luckily for us, his reps convinced him to stay, and his role as the reliable brother, Jack, is now considered one of the most desirable romantic male leads of all time.
Press Play (2022)
The baby, Lewis Pullman, has proven to be as impressive an actor as his father, with many people only recently realizing the familial connection, even though he is the spitting image of his father. That resemblance is not only skin deep, as anyone who watches this sweet film, which is an interesting mixture of science fiction and romantic drama, can attest. There are so many moments where Lewis gestures or enunciates exactly like his father, and it is a very cool thing to witness.
2. Adultery Done Right: Yes, it’s bad. But here, it looks good.
Brief Encounter (1945)
This wartime British tearjerker classic, directed by the incomparable David Lean, is one of his quietest and most intimate films. The grand epic scale we are used to in his work is here, but it is expressed through the depth of the romance between the two married lovers. Of course, situations could only be implied in cinema back then, but that kiss in the subway station is sexier than the majority of love scenes we see today.
Falling In Love (1984)
When you think of 1980s infidelity in cinema, you immediately reference Fatal Attraction. Millions of wives dragged their husbands to see the cautionary tale that took the notion of even thinking about cheating right out of their man’s mind, but no one wanted their spouse to see a film about two married people who do what the title says they do! This film had no chance of success due to its subject matter, even though it starred Robert De Niro and Meryl Streep, who had strong on-screen chemistry.
3. On the Other Hand — Save That Marriage!
Woman of the Year (1942)
The first pairing of Spencer Tracy and Katharine Hepburn is an all-timer and widely considered their best film together. As two work colleagues who are unlikely to fall for each other (as all movie co-workers are supposed to do), they trade not just the expected quips and jabs, but also some very poignant and serious moments dealing with the backdrop of WWII. The final scene is still debated among cinephiles as to whether or not it rings true for the characters, but you cannot deny that it is acted with absolute hilarity.
La Notte (1961)
One of Michelangelo Antonioni’s undeniable masterpieces of Italian cinema, and a very realistic look at the deterioration of a mid-century European marriage. A day and night in the life of an upper-class couple, who spend almost the entire runtime away from each other and in the arms of others. It is not until the devastatingly beautiful ending when the titular “note” is revealed that the film teaches us the true meaning of marriage.
4. What Do You See in Them?
Ball of Fire (1941)
The fish-out-of-water trope is one of the oldest in cinema, and when done right, as in this screwball comedy classic, audiences cannot help but love it. Yes, it is based on a play that is basically just a rehash of Snow White and the Seven Dwarfs, but here our dwarfs are nerdy professors and our princess is a showgirl. Gary Cooper plays the youngest, therefore most age-appropriate of the scholars who falls in love with Barbara Stanwyck’s 1940s streetwise gal, aptly named Sugarpuss. Of course, she gets him involved in a hair-brained criminal scheme, which turns out to be the perfect way for them to find love.
Once Around (1991)
This little-seen and little-known rom-com stars Holly Hunter as a member of a close-knit family who falls in love with an older and very abrasive salesman played by Richard Dreyfuss. This is probably the most irritating character he has ever played, but also one of his best performances. It is easy to understand how Hunter’s character, Renata, can love Dreyfuss’s Sam, because he is charming and treats her like a queen, which is something her overbearing parents and siblings never do. It is not all humor, however, and some of the best scenes are those where our mismatched couple shares their heartfelt best.
5. You’re Never Too Old for Romance.
Cass Timberlane (1947)
The older man/younger woman trope is just as entrenched in film history as the aforementioned fish-out-of-water, but most of the time it comes across as unrealistic or downright cringeworthy. Modern romance films seem to have that problem more than films of the past because older male stars knew better than to be paired with an ingénue. This film is a bit different because it takes an organic approach to how the characters meet and connect despite the misgivings of his stuffy legal friends.
Last Chance Harvey (2008)
The epitome of a great modern romantic drama, and what a certain segment of the population would refer to as a “grown folks film.” Dustin Hoffman plays the titular Harvey, who meets Emma Thompson’s equally lonely, but much younger, Kate, at the airport on the way to his daughter’s wedding. For the next two days, our couple talks and talks and talks. But what they have to say to each other, and more importantly, to us, about relationships is what makes this film more realistic, and ultimately, more hopelessly romantic than this two-hander has any right to be.
6. Romance Should Be Fun… and Silly!
One Touch of Venus (1948)
The first of the “a statue comes to life” rom-coms, which in this case was based on a Broadway musical. As with all of these films, a timid store employee fantasizes about the statue, kisses it, it enjoys being human, and thus begins a wacky, romantic adventure. The statue in this case is played by Ava Gardner, who transforms into the Greek goddess of love. She instantly falls in love with her hapless suitor, played by Robert Walker, who made a career out of roles like these. It is not a great film by any means, but it is a whole lot of fun.
Paris When It Sizzles (1964)
If you love films about writing, then this ridiculous rom-com is right in your wheelhouse. A successful screenwriter has one weekend to write a script he has had months to work on. Too busy enjoying life in Paris, he hires an assistant to get the job done. The film has a wonderfully comedic approach to writing and the budding romance in the first half, but the second half is filled with impossible scenarios in which the characters imagine themselves in the scenes they are writing. It would all fall flat on its face if it were not for the fact that our duo is played by two of the most magnetic and watchable movie stars ever, William Holden and Audrey Hepburn.
7. A Great Cinematic Pair: Robert Redford and Jane Fonda
Barefoot In the Park (1967)
Though not the first pairing of Redford and Fonda, this is the first in which their characters have a palpable romantic attachment. Redford reprised his role from the Neil Simon Broadway hit, and Fonda was already a friend from their first two films together, so it was only natural that she be cast as his newlywed wife. The two legendary stars collaborated on film five times, but it was this rom-com that solidified them as one of the greatest pairings in romantic cinema. Having this film as an archive of them when they were both budding movie stars is a valuable treasure.
Our Souls At Night (2017)
Fifty years later, our stars are now undeniable legendary actors, tireless activists, and lifelong friends. Making a film about the epidemic of loneliness among the elderly is a testament to their commitment to producing mature material in their golden years and to each other. Playing widowed neighbors who decide to get to know one another after years of living across the street, the film handles the romance in a purposefully subtle, yet surprisingly affectionate manner. After his passing, Fonda admitted that she was always in love with her friend, and who can blame her? In fact, I’m quite sure that, in our own way, we were all in love with Robert Redford, too.
8. So Good, We Had to Remake it Twice
The Shop Around the Corner (1940)
The original film is the most faithful and most heartfelt adaptation of the Hungarian stage play about two feuding shop clerks, who unknowingly are each other’s lovestruck pen pals, until one of them discovers the truth. Directed by the godfather of all comedy sub-genres, Ernst Lubitsch, he mixes the romance with some slapstick humor, a daring adultery sub-plot, and a whole lot of heart. As is usually the case, the first is the best.
In the Good Old Summertime (1949)
Well, of course, there should be a musical adaptation! This version of Parfumerie doubles down on the musical element by making the shop a musical-instrument store rather than a gift shop as in the previous version. Vincente Minelli directs his then-wife, Judy Garland, and Van Johnson as the couple, and wisely drops the cheating scandal for romantic tunes like “Meet Me Tonight in Dreamland” and the title track. Our stars do not have the chemistry that James Stewart and Margaret Sullavan had (mainly because Stewart was secretly in love with his best friend’s, Henry Fonda’s, then-wife), but the film itself is known as a shining example of a classic Hollywood musical.
You’ve Got Mail (1998)
Nora Ephron now takes a crack at the timeless tale and updates our couple into independent children’s bookshop owner Meg Ryan and megastore corporate bookshop owner Tom Hanks. The love letters are now emails, and all the modern-day bells and whistles (well-meaning friends, conscious uncoupling, multi-generational family dynamics, etc.) make this version feel more relatable to our current collective consciousness. If you are not familiar with the story, it is a good place to start, and then definitely watch the others.
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