Romance has a way of feeling personal, and People We Meet on Vacation taps into that magic perfectly. The story of Poppy and Alex, two friends whose connection spans years of shared vacations and quiet confessions, feels surprisingly close to home. Their chemistry, the bittersweet moments, and the small, seemingly ordinary interactions make it impossible not to root for them. For fans of this slow-burn romance with layers of humor, heartbreak, and hope, there’s a whole world of films that explore similar dynamics.
From charming love stories that start with a spark of serendipity to comedies where friendships turn into something more, this list dives into movies that capture the same emotional resonance, relatable characters, and immersive settings that make you feel like you’re part of the story. If Poppy and Alex’s journey stayed with you, these ten films are next on your watchlist.
1. Before Sunrise (1995)
Richard Linklater’s Before Sunrise is the kind of film that makes you believe in the possibility of instant connection. Jesse, an American, and Celine, a French student, meet by chance on a train and spontaneously decide to spend the night wandering Vienna together. Over the course of the evening, they talk, laugh, argue, and slowly open up to one another, revealing fears, dreams, and philosophies about life. Much like People We Meet on Vacation, the story relies less on dramatic plot points and more on the chemistry and authenticity of the characters. Poppy and Alex’s long-term friendship with underlying romantic tension is mirrored in Jesse and Celine’s fleeting but intensely personal encounter. The magic is in the little moments: a shared joke, a quiet pause, the vulnerability that comes with trusting someone new. Both films highlight how love can emerge from connection, understanding, and genuine attention to one another. Watching Before Sunrise feels like eavesdropping on a deeply intimate night, where every conversation feels loaded with meaning, much like the memorable interactions between Poppy and Alex across their vacations.
Must Check Out: 20 Great Travel Movies For Those Seeking Escapism
2. When Harry Met Sally (1989)
Rob Reiner’s When Harry Met Sally is a timeless exploration of friendship evolving into love, something fans of People We Meet on Vacation will instantly recognize. Harry and Sally meet by chance, clash over their differing views on relationships, and then reconnect repeatedly over the years, each encounter deepening their understanding of one another. Poppy and Alex’s dynamic is similar: years of friendship, shared experiences, and undeniable chemistry make their eventual romantic realization feel earned and deeply satisfying. What sets both films apart is their attention to the small, relatable moments—the banter, the arguments, the awkward yet charming conversations that reveal character and intimacy. The film’s humor is clever without being forced, and the emotional beats land with authenticity. Both stories explore the idea that love often grows slowly, nurtured by familiarity and timing. Watching Harry and Sally’s journey reminds viewers of the bittersweet beauty of long-term connection, the joy of discovering someone truly compatible, and the tension between desire and timing—elements that make Poppy and Alex’s story so relatable and heartwarming.
3. Always Be My Maybe (2019)
Ali Wong and Randall Park shine in Always Be My Maybe, a film that explores the enduring bond of childhood friendship blossoming into romance. Sasha and Marcus reconnect after years apart, confronting nostalgia, missed opportunities, and lingering feelings. The emotional resonance is similar to People We Meet on Vacation, where time and shared experiences create both tension and intimacy. Humor is central, yet the characters’ vulnerabilities make the romantic development believable and heartfelt. Poppy and Alex’s story thrives on the idea that a friend can also be the person you are most emotionally attuned to, a concept mirrored perfectly in Sasha and Marcus. Both films delve into the challenge of balancing past memories with present realities, showing how love can develop from deep-seated familiarity and trust. The witty dialogue, relatable awkwardness, and tender emotional beats in Always Be My Maybe make it feel like a modern counterpart to the nostalgic, vacation-centered, slow-burn romance of Poppy and Alex. For viewers seeking a charming, laugh-out-loud romance with heartfelt undertones, this film is a must-watch.
4. Plus One (2019)
Plus One is a contemporary romantic comedy that perfectly captures the playful, banter-filled dynamic seen in People We Meet on Vacation. Ben and Alice, friends navigating wedding season together, experience awkward social situations, unexpected chemistry, and slowly growing attraction. The film excels in showing how friendship can be a fertile ground for romance, with tension and humor arising naturally from shared history. Like Poppy and Alex, Ben and Alice navigate unspoken feelings and realize the depth of their connection over time. Both films emphasize that love can develop in the spaces between casual interactions, small gestures, and moments of vulnerability. The pacing allows the audience to settle into their relationship gradually, enjoying both the comedic mishaps and tender emotional moments. The relatability of their friendship, combined with slow-burn romance and witty exchanges, makes Plus One a perfect companion piece to People We Meet on Vacation, offering a blend of laughter, longing, and satisfying romantic payoff.
Read More: The 50 Best Films Of 2019
5. Drinking Buddies (2013)
Joe Swanberg’s Drinking Buddies explores the delicate boundaries between friendship and romance, making it a natural fit for fans of People We Meet on Vacation. Kate and Luke work together at a brewery, sharing casual drinks, flirtation, and deep conversations. The film emphasizes naturalistic dialogue and slow-developing tension, mirroring the comfort and subtle chemistry between Poppy and Alex. Both films highlight how emotional intimacy can exist independently of romance, yet also evolve into it over time. Watching the characters navigate the “what ifs” of love and friendship feels deeply familiar, as moments of connection are understated yet profoundly impactful. The charm lies in its realism: relationships are messy, nuanced, and emotionally honest. Fans of Poppy and Alex’s relationship will recognize that same mixture of comfort, humor, and longing in Kate and Luke, making Drinking Buddies a quietly affecting, emotionally rich watch that celebrates the complexity of close bonds and the allure of slow-burn romance.
6. What If (2013)
‘What If’ is a tender, witty exploration of friendship teetering on the edge of romance. Wallace and Chantry have a natural rapport, inside jokes, and shared history, similar to the dynamic between Poppy and Alex. Their story revolves around timing, emotional vulnerability, and the risk of jeopardizing a treasured friendship for love. Both films show that deep emotional connections can be just as compelling as traditional romantic setups, relying on nuanced performances and realistic dialogue. Humor, awkwardness, and genuine affection dominate the narrative, making every interaction feel relatable. Poppy and Alex’s vacations and Wallace and Chantry’s encounters share a sense of intimacy born from knowing someone well, and the tension between comfort and desire drives the emotional stakes. Watching What If evokes the same mixture of hope, nostalgia, and delight that makes People We Meet on Vacation resonate, providing a story where love emerges from friendship with heart and authenticity.
7. Red, White & Royal Blue (2023)
Red, White & Royal Blue tells the story of Alex Claremont-Diaz and Prince Henry, whose initial rivalry gradually transforms into genuine affection and romantic intimacy. The dynamic of witty banter, long-standing familiarity, and emotional vulnerability closely mirrors Poppy and Alex’s relationship. Both films highlight how love can evolve from connection, shared history, and mutual understanding. The stakes in Red, White & Royal Blue are higher due to political and public pressures, yet the emotional core is relatable: two people navigating attraction, trust, and timing. Humor and tenderness are balanced with moments of genuine vulnerability, echoing the playful yet heartfelt energy of People We Meet on Vacation. The film captures the thrill of slow-burning romance, the satisfaction of seeing chemistry develop, and the warmth of shared experience. Fans of stories where friendship evolves into love will find this modern romantic tale both charming and emotionally resonant.
More Movies Like ‘People We Meet on Vacation’: 6 Movies to Watch if you like ‘Red, White & Royal Blue’ on Prime Video
8. The Notebook (2004)
Nick Cassavetes’ The Notebook is an epic romance about enduring love that resonates with the emotional undertones of People We Meet on Vacation. Noah and Allie’s story spans years, exploring the push and pull of timing, choice, and personal growth. Poppy and Alex share similar themes: longing, missed opportunities, and the bond that persists despite distance and change. The film emphasizes that love is often built on small, intimate moments—shared conversations, letters, and unspoken understanding—just as the charm of Poppy and Alex’s vacations lies in subtle gestures. The intensity of The Notebook is grander, yet the emotional truths align: love is messy, deeply felt, and often shaped by friendship, trust, and patience. Watching it reminds viewers why slow, heartfelt romance grounded in genuine connection is so impactful, making it an essential watch for fans of Poppy and Alex’s story.
