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Valentine's Day may mean different things for everyone. Some may be spending it with a significant other, while others may be spending it with their friends, while others may just spend it alone, having a relaxing night in. Whatever the case may be, having a fresh movie to watch can get you in the Valentine's Day spirit. From time-loop comedies to gentle indie romances, these five overlooked movies explore love from every angle, and remind us that sometimes the most meaningful love stories are the ones we almost miss.
Palm Springs (2020)
Groundhog Day meets Eternal Sunshine of the Spotless Mind in this sci-fi romcom, a clever time-loop comedy blended with an unexpectedly tender, existential love story. Starring Andy Samberg and Cristin Milioti, two actors known predominantly for their roles in network television sitcoms Brooklyn 99 and How I Met Your Mother, this movie showcased a much broader acting range for both stars. Produced by comedy trio The Lonely Island, consisting of Andy Samberg, Akiva Schaffer, and Jorma Taccone, the humor is top-notch, but it has an emotional depth to it not seen in their other works.
In this movie, carefree Nyles (Andy Samberg) and reluctant maid of honor Sarah (Cristin Milioti) get stuck in a time loop at a wedding, forced to relive the same day over and over again. As they navigate the endless, existential loop together, they develop a deep bond while coming to terms with their brokenness as people.
Released during the height of COVID, this film did poorly at the box office, earning only $1.5 million against its $5 million budget. However, it has slowly gained a cult following since its release, spreading through online spaces and word of mouth, becoming known as a hidden gem romcom movie.
Runtime: 90 minutes
Down With Love (2003)
This is not your average rom-com. An early-2000s pastiche of early ’60s “no-sex comedies,” Down with Love blends the charm of classic Hollywood with postmodern sensibilities. It playfully engages with feminist ideas, creating an intriguing tension between its retro aesthetic and its overt discussions of sex, desire, and independence. While it lovingly mimics the conventions of mid-century Hollywood romance, it also subverts them, resulting in a movie that feels both nostalgic and surprisingly progressive.
The cast elevates the material even further, bringing charisma, wit, and impeccable comedic timing to the film (who doesn’t love Ewan McGregor and Renée Zellweger?). Visually, the film leans fully into its aesthetic, using bold colors and stylized sets that make it feel like you're watching a modern-day Technicolor masterpiece.
Set in 1962, the story follows feminist author Barbara Novak (Renée Zellweger), whose best-selling book encourages women to abandon traditional romance in favor of independence. Her massive success unsettles many men, including slick magazine writer Catcher Block (Ewan McGregor), who sets out to expose her as a fraud by making her fall in love with him, only to find out something shocking in the process.
Runtime: 101 minutes
The Ballad of Wallis Island (2025)
Released quietly last year, The Ballad of Wallis Island tells the story of Herb McGwyer (Tom Basden) and Nell Mortimer (Carey Mulligan), a former folk music duo who reunite to perform for Charles Heath (Tim Key), a wealthy superfan living alone on a remote British island. What begins as a simple private concert gradually unfolds into a tender meditation on love, regret, and the complicated emotions tied to revisiting the past.
Written by Tim Key and Tom Basden, the film originated as a short titled The One and Only Herb McGwyer Plays Wallis Island (2007), which received widespread acclaim, including a nomination for the 2008 BAFTA Award for Best Short Film. Expanding the story into a feature allowed its humor and emotional depth to fully breathe, creating a quietly affecting experience for audiences.
Funny, contemplative, and full of innocent charm, this small film packs an unexpected emotional punch. It explores the importance of letting go, finding contentment, and learning to slow down, which are lessons that resonate especially now, in a world that rarely seems to pause. With its limited release, it may have flown under the radar, but for anyone craving a reflective and cozy night in, The Ballad of Wallis Island is a hidden gem.
Runtime: 100 minutes
Hold Me Back (2020)
A Japanese film directed by Akiko Ohku, Hold Me Back is a visually imaginative and emotionally resonant exploration of anxiety, loneliness, and modern romance. Blending whimsy with introspection, the film uses playful visual flourishes to externalize its protagonist’s inner world, turning everyday uncertainty into something tender, funny, and deeply relatable. Poignant yet humorous, it ultimately becomes a gentle meditation on the importance of opening yourself up to change, even if it feels terrifying.
While the film remains a romantic comedy at heart, it explores the psychological condition of its protagonist in a deeply original way. By giving voice to Mitsuko’s inner thoughts, Hold Me Back allows us to understand her not as she presents herself to the world, but as she truly is. We see her quirks, insecurities, fleeting pettiness, and private hopes, which all make up the messy, unfiltered thoughts that shape everyday life. This intimate access makes her feel startlingly real, offering a refreshingly honest portrayal of womanhood, social pressure, and self-doubt. As a result, Mitsuko becomes an incredibly relatable figure that the viewer can easily see themselves in, because her emotional landscape feels so familiar.
Mitsuko Kuroda (Non) is 31, single, and content with her carefully curated everyday routine. Much of her comfort comes from her inner counselor, “A,” a manifestation of her conscience that offers guidance whenever she feels uncertain. But when she begins to fall for Tada, a younger salesman who lives in her neighborhood, Mitsuko is forced to confront her anxieties, loneliness, and fear of vulnerability, pushing her to step beyond the safety of her inner world and into the unpredictability of real connection.
Runtime: 133 minutes
Set It Up (2018)
The internet often credits Set It Up with sparking the modern romcom revival, and honestly, it’s hard to disagree. Everything aligned for this film: sharp writing, impeccable timing, and a cast bursting with star power, established and emerging alike. Glen Powell’s performance in this film cemented him as a romcom leading man (a trajectory that later led to hits like Anyone But You), while Zoey Deutch brought warmth, wit, and emotional depth. Meanwhile, Lucy Liu, already a romcom icon, added extra charm, building on her legacy from films like Watching the Detectives (2007).
What truly makes this movie shine is how confidently it embraces the classic romcom blueprint without feeling overly cheesy. It delivers enemies-to-friends-to-lovers, witty banter, workplace romance, and parallel A and B plots, all while knowing exactly how to cater to its audience. The humor lands especially well with millennials, capturing workplace burnout, dating fatigue, and career anxiety, yet it avoids becoming overly “cringe” or dated, allowing it to still resonate with younger viewers. The result is a film with just the right balance of humor, chemistry, and emotional sincerity.
The story follows Harper (Zoey Deutch) and Charlie (Glen Powell), two underpaid, overworked assistants whose lives revolve around catering to their demanding bosses. Hoping to reclaim some control, they hatch a scheme to set their bosses up with each other, only to discover in the process that they might have more chemistry with one another than they ever anticipated.
Runtime: 105 minutes
