Movies Like When Harry Met Sally: Best Romantic Comedy Look

Embarking on a cinematic journey through movies like When Harry Met Sally can be a delightful dive into the world of romantic comedies, where love, laughter, and life lessons affect in the most enchanting ways. This iconic film has set a benchmark for the genre, blending clever thinking, unforgettable characters, and the timeless question of whether men and women can ever be just friends.

As we explore films that capture the same magic and warmth, we invite you to join us in rediscovering the charm of romantic comedies that resonate with the spirit of When Harry Met Sally. From tales of unexpected love to narratives of friendship blossoming into romance, this blog will guide you through a carefully curated selection of films.

Hopefully, you will find the real entertainment that promises to reignite your love for heartfelt storytelling and comedic brilliance. Get ready to fall in love all over again with movies that remind us of the joy and complexities of relationships, all while echoing the unforgettable essence of a true rom-com classic.

Movie NameWhen Harry Met Sally
ProducerRob Reiner
DirectorRob Reiner
First ReleaseJuly 14, 1989
Running time96 minutes
Budget$16 million
Box Office$92.8 million

When Harry Met Sally Plot

Dive into the heartwarming narrative of “When Harry Met Sally,” a deep romantic comedy that explores the evolving dynamics between two New Yorkers, Harry Burns and Sally Albright. Their journey begins with a chance encounter as they share a car ride from Chicago to New York, marking the start of a complex friendship. 

Over the years, through chance meetings and significant life changes, they debate whether men and women can maintain a nonsexual relationship without romance getting in the way. The movie charmingly navigates through their personal growth, humorous exchanges, and the deepening of their bond, leading to the realization that love often blossoms in the most unexpected circumstances. 

With its engaging plot and memorable dialogues, this timeless classic captures the essence of love, friendship, and the unexpected nature of true connections, making it a must-watch for rom-com enthusiasts.

When Harry Met Sally Plot

Box Office Collection

North America$92.8 million
Running Time96 minutes
Budget$16 million

20 Movies Like When Harry Met Sally

Embark on a delightful cinematic journey with 20 movies like “When Harry Met Sally,” each covering with the charm, attention of mind, and heartwarming romance that made the original a classic. These films capture the essence of unexpected love and the complexity of human relationships, much like our beloved Harry and Sally.

From the enchanting encounters in “Sleepless in Seattle” to the quirky love story of “You’ve Got Mail,” each movie offers a unique take on love, friendship, and the serendipitous moments that unite people.

Dive into the timeless appeal of “The Holiday” or enjoy the modern twists of “Love, Rosie.” When Harry Met Sally movies like stories include laughter, tears, and the irresistible thrill of rooting for love against all odds. Perfect for cozy nights in or weekend movie marathons, this curated list is your gateway to rediscovering the magic of romantic comedies.

The Princess Diaries (2001)

Movie NameThe Princess Diaries (2001)
DirectorGarry Marshall
ProducerWhitney Houston
Release DateJuly 29, 2001
Total Budget$26 million
Gross Profit$165.3 million

Dive into the enchanting world of “The Princess Diaries” (2001), a heartwarming tale that captures the transformation of Mia Thermopolis, a shy and awkward teenager, into a graceful princess. Living a low-profile life in San Francisco, Mia’s world turns upside down when the lady learns she is the sole heir to the throne of a European kingdom, Genovia.

Guided by her regal grandmother, Queen Clarisse Renaldi, Mia embarks on a remarkable journey of self-discovery and royal training. From navigating the risks of etiquette lessons to dealing with the sudden spotlight, Mia faces the daunting challenge of balancing her ordinary life with her newfound royal responsibilities.

This delightful story, filled with humor, romance, and life lessons, resonates with the dreamer in all of us. It showcases the journey to find one’s true self amidst the chaos of adolescence and royal duty. 

The Princess Diaries (2001)

Long Shot (2019)

Movie NameLong Shot (2019)
DirectorJonathan Levine
ProducerCharlize Theron
Release DateMarch 9, 2019
Total Budget$40 million
Gross Profit$53.9 million

Dive into the engaging and humorous world of “Long Shot” (2019), where the unlikely duo of Fred Flarsky, a free-spirited journalist, and Charlotte Field, the elegant and driven Secretary of State, come together in a whirlwind of politics, romance, and laughter. 

When Fred unexpectedly reunites with Charlotte, his childhood crush and babysitter, he finds himself swept up in her world of high-stakes diplomacy as she prepares to make a run for the Presidency. Despite their contrasting personalities and the initial skepticism of those around them, the chemistry between Fred and Charlotte ignites, leading to a series of comedic and heartfelt moments. 

“Long Shot” cleverly navigates the realms of political ambition and the unpredictability of love, proving that opposites can attract and that, sometimes, the most unexpected pairings make the best teams. This movie offers a refreshing take on the romantic comedy genre, blending humor with a touch of political contrast.

Long Shot (2019)

How to Lose a Guy in 10 Days (2003)

Movie NameHow to Lose a Guy in 10 Days (2003)
DirectorDonald Petrie
ProducerLynda Obst
Release DateFebruary 7, 2003
Total Budget$50 million
Gross Profit$177.5 million

The playful and engaging plot of “How to Lose a Guy in 10 Days” (2003) tells an entertaining story where the worlds of love and wagers collide in a comedic showdown. For her latest article, an aspiring journalist, Andie Anderson takes on a unique challenge: to start a relationship and commit to every possible dating to drive the man away within ten days. 

Enter Benjamin Barry, an advertising executive who bets he can make any woman fall in love with him in the same timeframe. Unknown to each other’s motives, Andie and Ben’s relationship becomes a battlefield of wits and wills, leading to unexpected romantic sparks amidst their cunning plans. This film masterfully combines humor, romance, and a touch of irony.

How To Lose A Guy In 10 Days Plot

How to Be Single (2016)

Movie NameHow to Be Single (2016)
DirectorChristian Ditter
ProducerJohn Rickard
Release DateFebruary 9, 2016
Total Budget$38 million
Gross Profit$112.3 million

Explore the vibrant and often comedic journey of self-discovery in “How to Be Single” (2016), where young New Yorkers navigate the complexities of relationships and the joys of single life in the city that never sleeps. 

Alice temporarily steps away from her long-term relationship to find herself but quickly learns that embracing singlehood in New York is a whirlwind of adventures, mishaps, and personal growth. Alongside her fiercely independent friend Robin, her sister Meg, and her co-worker Lucy, Alice embarks on their paths to understanding love, life, and happiness outside the confines of traditional relationships. 

This film cleverly blends multiple stories, showcasing the varying perspectives on single life, the importance of friendship, and the realization that fulfillment comes from within. “How to Be Single” offers a fresh take on the rom-com genre, celebrating the individual journey in the quest for love and identity.

How to Be Single (2016)

She’s the Man (2006)

Movie NameShe’s the Man (2006)
DirectorAndy Fickman
ProducerLauren Shuler Donner
Release DateMarch 17, 2006
Total Budget$20–25 million
Gross Profit$57.2 million

“She’s the Man” (2006) is a delightful twist on Shakespeare’s “Twelfth Night,” set in the contemporary world of high school soccer and teenage romance. Viola Hastings denied the chance to play on the boys’ soccer team, creates a bold plan to disguise herself as her twin brother, Sebastian, and take his place at his new boarding school to prove her soccer interest. 

The trick leads to a comedic flow of events, including unexpected romantic entanglements and misunderstandings. Viola navigates the complexities of high school life, from rivalry on the soccer field to navigating the involvement of love and friendship, all while maintaining her disguise. 

This energetic and heartwarming film combines humor, romance, and the timeless theme of pursuing one’s dreams against all odds, making it a memorable addition to the teen comedy genre.

She's the Man (2006)

The Lovebirds (2020)

Movie NameThe Lovebirds (2020)
DirectorMichael Showalter
ProducerTom Lassally
Release DateMay 22, 2020
Running time87 minutes
Total Budget$16 million

“The Lovebirds” (2020) unravels an action-packed romantic comedy where a couple on the brink of a breakup, Leilani and Jibran, find themselves involved in a strange murder mystery. When they attempt to clear their names, a wild and unpredictable night ensues, taking them from one risky situation to another across the city; that particular adventure forces them to work together, reigniting their fading spark and testing the strength of their relationship. 

Amidst the chaos of car chases, bizarre cult gatherings, and unexpected encounters with criminals, the duo discovers the true meaning of love and partnership. This film masterfully blends comedy, romance, and thriller elements, offering viewers an entertaining ride filled with laughter, suspense, and heartwarming moments. It showcases how sometimes the most challenging situations can bring people closer together.

The Lovebirds (2020)

Bringing Up Baby (1938)

Movie NameBringing Up Baby (1938)
DirectorHoward Hawks
ProducerCliff Reid
Release DateFebruary 16, 1938
Total Budget$1.1 million
Gross Profit$1.1 million

“Bringing Up Baby” (1938) is a classic eccentric comedy that stands the test of time with its delightful mix of chaos, romance, and humor. The story revolves around the unlikely duo of mild-mannered fossilist David Huxley and the free-spirited and eccentric heiress Susan Vance. Their worlds collide when Susan, in a series of misadventures, involves David in caring for a leopard named Baby. 

The plot thickens with a missing dinosaur bone, mistaken identities, and a series of comedic mishaps that lead them through a whirlwind of events. As they navigate through the chaos, David and Susan’s initial annoyance with each other blossoms into love. This film is celebrated for its witty dialogue, charming characters, and seamless blend of comedy and romance. It is a typical example of the genre and a timeless classic in cinematic history.

Bringing Up Baby (1938)

Palm Springs (2020)

Movie NamePalm Springs (2020)
DirectorMax Barbakow
ProducerAndy Samberg
Release DateJanuary 26, 2020
Total Budget$5 million
Gross Profit$1.5 million

“Palm Springs” (2020) presents a refreshing take on the romantic comedy genre with a unique twist. The story unfolds at a wedding in Palm Springs, where Nyles, a carefree wedding guest, meets Sarah, the reluctant maid of honor. Their chance encounter turns without expectations when they find themselves trapped in a time loop, repeatedly reliving the same day. 

As they navigate the coincidences of their endless time loop, Nyles and Sarah embark on a journey filled with hilarious thirst, heartfelt moments, and the exploration of life’s endless possibilities. Their shared experiences bring them closer, challenging their perceptions of life, love, and happiness. 

“Palm Springs” combines humor with a thought-provoking narrative, offering a clever and entertaining exploration of human connections and the search for meaning in the monotony of life. Palm Springs is one of the similar movies like When Harry Met Sally that provides charm.

Palm Springs (2020)

Crazy, Stupid, Love. (2011)

Movie NameCrazy, Stupid, Love. (2011)
DirectorGlenn Ficarra
ProducerSteve Carell
Release DateJuly 19, 2011
Total Budget$50 million
Gross Profit$145 million

“Crazy, Stupid, Love.” (2011) weaves a multifaceted story of love, heartbreak, and rediscovery. At the heart of the film is Cal Weaver, a middle-aged man whose life unravels when he learns of his wife Emily’s infidelity and subsequent request for a divorce. Thrust back into the dating world, Cal meets the suave and charismatic Jacob Palmer, who takes him under his wing to teach him the art of attracting women. 

As Cal navigates his new lifestyle, the plot thickens with bending love stories involving his children and close acquaintances, painting a complex picture of romantic and familial relationships. The film masterfully balances humor with emotional depth, showcasing love’s unpredictable and often messy nature. This leads to revelations that bring the characters closer to understanding true love and connection.

Crazy, Stupid, Love. (2011)

Marry Me (2022)

Movie NameMarry Me (2022)
DirectorKat Coiro
ProducerElaine Goldsmith-Thomas
Release DateFebruary 9, 2022
Total Budget$23 million
Gross Profit$50.5 million

“Marry Me” (2022) is a modern romantic comedy that captures the unexpected twists of love in the limelight. The story centers around Kat Valdez, a global pop superstar assured to marry her on-stage partner before a live audience of millions. 

However, moments before the ceremony, she discovers his betrayal. In a spontaneous act of disobedience, Kat chooses to marry Charlie, a math teacher, and a stranger in the crowd holding a “Marry Me” sign. What starts as a thoughtless reaction to a public scandal evolves into a genuine connection and discovery journey for Kat and Charlie. 

As their worlds collide, they navigate the challenges of their unconventional relationship under the watchful eyes of the public and media, learning about love, trust, and the courage to embrace the unexpected. “Marry Me” blends humor with heart, offering a fresh perspective on finding love in the most unexpected places.

Marry Me (2022)

This Is 40 (2012)

Movie NameThis Is 40 (2012)
DirectorJudd Apatow
ProducerJudd Apatow
Release DateDecember 21, 2012
Total Budget$35 million
Gross Profit$88.1 million

“This Is 40” (2012) delves into the humorous yet relatable complexities of family life and aging. The film serves as a “sort-of sequel” to “Knocked Up,” focusing on Pete and Debbie, a married couple grappling with the realities of reaching 40. 

Amidst the celebration and apprehension of entering mid-life, they confront the challenges of parenting, marriage, financial pressures, and pursuing personal dreams. The narrative humorously showcases their efforts to revive their relationship, manage a chaotic household, and balance their professional ambitions while maintaining a sense of self. 

“This Is 40” captures the essence of family dynamics, the struggles of adulting, and the quest for happiness. It is an emotional comedy that resonates with anyone navigating the ups and downs of life’s middle passage. Watch this similar movie to enjoy more movies like When Sally Met Harry.

This Is 40 (2012)

Monster-in-Law (2005)

Movie NameMonster-in-Law (2005)
DirectorRobert Luketic
ProducerChris Bender
Release DateMay 5, 2005
Total Budget$43 million
Gross Profit$154.7 million

“Monster-in-Law” (2005) is a comedic exploration of the complicated relationship between a future bride and her overbearing future mother-in-law. The film follows Charlotte ‘Charlie’ Cantilini, a carefree and kind-hearted woman who finally meets the man of her dreams, Kevin Fields.

However, her fairy-tale romance takes a turn when she encounters Kevin’s mother, Viola, a renowned news anchor recently replaced by a younger counterpart. This makes her cling to her son even more. Determined to protect her son at all costs, Viola sets out to make Charlie’s life a nightmare, initiating a series of comedic and outrageous attempts to sabotage the engagement.

The ultimate battle of mental sharpness between Charlie and Viola leads to a series of laugh-out-loud moments, ultimately exploring themes of love, family, and the lengths one will go to keep them together.

Monster-in-Law (2005)

There’s Something About Mary (1998)

Movie NameThere’s Something About Mary (1998)
DirectorPeter Farrelly
ProducerMichael Steinberg
Release DateJuly 15, 1998
Total Budget$23 million
Gross Profit$369.9 million

“There’s Something About Mary” (1998) is a standout romantic comedy that combines humor with a touch of heart. The story starts with a flashback to Ted’s awkward teenage years, when he experiences a humiliating incident during his walk-in night with his dream girl, Mary. Fast forward several years, and Ted is still hung up on what could have been. 

Determined to discover what happened to Mary, he hires a private detective, Pat Healy, to track her down. However, Healy becomes obsessed with Mary’s charm and decides to pursue herself, leading to multiple suitors’ comedic and competitive antics, all vying for Mary’s affection. 

The film masterfully blends slapstick humor with genuine moments of sensitivity, making it a memorable tale of unrequited love and the lengths one will go to win over the heart of one’s beloved. 

There's Something About Mary (1998)

Meet Cute (2022)

Movie NameMeet Cute (2022)
DirectorAlex Lehman
ProducerAkiva Goldsman
Release DateSeptember 21, 2022
Running time89 minutes
Original LanguageEnglish

“Meet Cute” (2022) presents a captivating twist on the classic romantic comedy genre, filling time travel into a tale of love and self-discovery. The plot centers around Sheila and Gary, who experience what appears to be the perfect first date, only to reveal a deeper, more complex layer to their encounter.

Sheila possesses a time machine, which she uses to repeatedly return to relive their first date, each time attempting to perfect their relationship and fix Gary’s flaws. However, as she manipulates time to create the ideal partner, Sheila confronts profound questions about love, acceptance, and the nature of true happiness. 

This inventive narrative combines humor, romance, and philosophical musings on the essence of connection, challenging the conventional boundaries of the meet-cute image and offering a fresh, thought-provoking take on the power of accepting loved ones as they are.

Meet Cute (2022)

Made of Honor (2008)

Movie NameMade of Honor (2008)
DirectorPaul Weiland
ProducerNeal H. Moritz
Release DateMay 2, 2008
Total Budget$40 million
Gross Profit$106.4 million

“Made of Honor” (2008) spins the traditional romantic comedy narrative with its unique premise and charming characters. The story revolves around Tom and Hannah, who have been best friends for years. Tom is a serial dater, while Hannah is searching for Mr. Right. 

When Hannah travels to Scotland and gets engaged, Tom realizes his feelings for her run deeper than friendship. In a twist of fate, Hannah asks Tom to be her ‘Maid of Honor,’ putting him in the perfect position to win her heart before she walks down the aisle. 

Tom must navigate wedding plans and bridal showers while plotting to confess his true feelings. This film cleverly plays with the roles of love and friendship, blending humor with heartfelt moments, making “Made of Honor” a delightful tale of unrequited love turning into a potential happily ever after.

Made of Honor (2008)

500 Days of Summer (2009)

Movie Name500 Days of Summer (2009)
DirectorMarc Webb
ProducerMason Novick
Release DateJanuary 17, 2009
Total Budget$7.5 million
Gross Profit$60.7 million

“500 Days of Summer” (2009) is a non-linear romantic dramedy that delves into the highs and lows of modern love through the eyes of Tom, a hopeless romantic who falls for the enigmatic Summer. Unlike typical love stories, this film elaborates on their relationship in a scattered timeline, highlighting the joyful beginnings and the eventual heartbreaks.

After his breakup, Tom’s journey of reflection and self-discovery redefines his understanding of love and fate. The movie’s innovative storytelling and relatable characters challenge the conventional notions of romantic narratives, making it an emotional exploration of love’s complexities and the importance of personal growth in the aftermath of a relationship.

500 Days of Summer (2009)

The Hating Game (2021)

Movie NameThe Hating Game (2021)
DirectorPeter Hutchings
ProducerClaude Dal Farra
Release DateDecember 10, 2021
Running Time102 minutes
Gross Profit$294,625

“The Hating Game” (2021) is a captivating romantic comedy exploring love and rivalry’s fiery dynamics. Lucy Hutton and Joshua Templeman are executive assistants with contrasting personalities who work for the co-CEOs of a publishing company. Their professional competition is unmatched, and they engage in a daily battle of wits and wills. 

However, their rivalry reaches new heights when a promotion is announced, forcing them to confront the thin line between love and hate. As they vie for the same job, their antagonistic interactions spark an unexpected attraction, leading them to reevaluate their feelings for each other. 

This film masterfully blends humor, tension, and romance, offering a fresh take on the enemies-to-lovers trope. It makes “The Hating Game” a delightful journey through the complexities of office romance and the unpredictable nature of the heart.

The Hating Game (2021)

Rosaline (2022)

Movie NameRosaline (2022)
DirectorKaren Maine
ProducerShawn Levy
Release DateOctober 6, 2022
Running Time96 minutes

“Rosaline” (2022) is a clever and engaging retelling of Shakespeare’s classic tale of “Romeo and Juliet,” but with a refreshing twist. The story is told from the perspective of Rosaline, Romeo’s ex-lover, who is determined to foil the infamous romance between Romeo and Juliet and win back her boyfriend. 

The movie is set against the backdrop of Renaissance Verona; Rosaline employs humor, schemes, and a touch of mischief to disrupt the budding love affair. Her journey is filled with humorous excitement, unexpected alliances, and insights into love’s complexities. 

This unique take on a timeless story combines comedy, romance, and historical drama, offering viewers a delightful and modern interpretation of Shakespeare’s work. “Rosaline” brilliantly showcases how perspective can transform a well-known tale into a new and enchanting narrative.

Rosaline (2022)

Two Weeks Notice (2002)

Movie NameTwo Weeks Notice (2002)
DirectorMarc Lawrence
ProducerSandra Bullock
Release DateDecember 20, 2002
Total Budget$60 million
Gross Profit$199 million

“Two Weeks Notice” (2002) is a charming romantic comedic entry. Its wit, romance, and heart blend evoke When Harry Met Sally-like movies. The film centers around Lucy Kelson, a brilliant but idealistic lawyer, and George Wade, a wealthy real estate powerful person who relies on Lucy for virtually every decision. 

Frustrated by her role as George’s de facto nanny rather than a legal mind, Lucy resigns, giving her two weeks’ notice. However, as they search for her replacement and navigate their final days working together, Lucy and George discover an unexpected bond, leading them to question their feelings for each other. This delightful comedy explores themes of love, career, and the importance of finding balance, making it a must-watch for fans of classic romantic comedies.

Two Weeks Notice (2002)

Just Go with It (2011)

Movie NameJust Go with It (2011)
DirectorDennis Dugan
ProducerAdam Sandler
Release DateFebruary 8, 2011
Total Budget$80 million
Gross Profit$215 million

“Just Go with It” (2011) is a lighthearted romantic comedy that captures the essence of unexpected love. It is a delightful addition to the list of movies like When Harry Met Sally. The film follows the story of Danny, who pretends to be an expert plastic surgeon and lives in unhappy marriages to attract women.

Upon encountering the enchanting Palmer, Danny’s scheme unravels, prompting him to recruit his devoted assistant, Katherine, to imitate his forthcoming former spouse to sustain the trick.

The situation spirals out of control when Katherine’s children become involved, leading to comedic and heartwarming misadventures on a Hawaiian vacation. As Danny and Katherine play their parts, they realize their true feelings for each other, showcasing the unpredictable nature of love and the beauty of finding it in the most unlikely places.

Just Go with It (2011)


In wrapping up our exploration of best movies like When Harry Met Sally, it’s clear that the charm of romantic comedies lies in their ability to blend humor with the complexities of love and relationships. Each film we’ve discussed offers a unique perspective on romance, echoing the presence of mind, emotional depth, and memorable moments, making “When Harry Met Sally” a genre-defining classic. 

For those seeking movies to watch if you like When Harry Met Sally, our selection provides a diverse array of narratives, from unexpected love stories to tales of friendship turning into romance, that capture the essence of what makes romantic comedies so enduringly appealing.

Whether you’re in the mood for laughter, tears, or a bit of both, these films are sure to deliver the perfect romantic comedy experience, reminding us of the joy and unpredictability of love.

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Jordan Counsel

Jordan Counsel is a passionate movie enthusiast with a keen eye for cinematic details. With years of experience in the film world, Jordan brings a unique perspective to the art of movie analysis and critique. Whether dissecting the latest blockbuster or delving into the nuances of independent cinema, Jordan's writing provides readers with insightful and engaging content. When not glued to the silver screen, Jordan enjoys exploring the world of cinema, attending film festivals, and sharing recommendations for movie lovers everywhere.