Moonstruck (1987) is a quirky, fun rom-com that has made an impact on the genre in a myriad of ways. Not only did this romantic comedy earn Cher an Academy Award for Best Actress, but it also embedded her delivery of the line “snap out it!” (followed by a powerful slap to Nicolas Cage) deep into pop culture. Moonstruck follows Loretta Castorini (Cher) — a widow who begins to fall in love with her fiancé’s brother, Ronny (Cage).
This movie is as playfully chaotic as any movie about falling in love with your fiancé’s brother should be. It also has great acting, witty dialogue, and absurdly hilarious plots (re: Ronny’s wooden hand.) There’s nothing to dislike about this movie, and it’s perfect for a night where you just want to laugh (and maybe see Cage get slapped).
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24. Runaway Bride
Runaway Bride (1999) reunites Julia Roberts, Richard Gere, and director Garry Marshall for another romp around the rom-com genre — nine years after their success with Pretty Woman. Starkly different in tone and plot from Pretty Woman, Runaway Bride follows small town girl Maggie Carpenter (Roberts) as she’s profiled by journalist Ike Graham (Gere.) Maggie has run away from three separate weddings, and in the midst of her fourth engagement, Ike sets out to report on if she’ll make it down the aisle this time around.
Not every movie can be perfect, and this one definitely isn’t. However, it’s still deeply enjoyable, and a lighthearted watch. Not to mention, the chemistry between Roberts and Gere remains palpable — watching those two fall in love is never a bad time.
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23. Set It Up
Set It Up (2018) is a Netflix rom-com starring Zoey Deutch and Glen Powell. The two play Harper and Charlie, who are overworked and miserable at their jobs as assistants to corporate bosses. In hopes of making their lives easier, they devise a plan to matchmake their respective bosses — but fall for each other in the process.
Deutch and Powell have such excellent chemistry in this, it makes me hope they take the Adam Sandler/Drew Barrymore route and keep making rom-coms together for as long as they can. On top of that, this movie is a fun and fresh look at how two people can fall in love without even trying. In an era that doesn’t have too many new and exciting romantic comedies in theaters, this one embraces the fundamental parts of the genre that made it so popular to begin with and combines it with a fresh plot, up and coming actors, and great comedy.
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22. You’ve Got Mail
While Marvel has the MCU (Marvel Cinematic Universe), Nora Ephron has the MRCU (Meg Ryan Cinematic Universe.) You’ve Got Mail marks her third collaboration with Ryan, and second with Tom Hanks. Ryan plays Kathleen Kelly, a small bookshop owner at odds with Joe Fox. Fox is moving his chain bookstore, Fox Books, into her neighborhood. While the two clash in person, they unknowingly chat anonymously over AOL Messenger, and develop feelings for one another. This film truly embraces the fun that an enemies-to-lovers arc can be when done correctly. Ryan and Hanks have great chemistry, and watching them love to hate each other keeps the movie exciting!
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21. The Wedding Singer
The Wedding Singer is not just a fun and colorful time capsule of the 1980s, but it also marks the first movie that Drew Barrymore and Adam Sandler star in together. Sandler plays Robbie, a wedding singer who loses his belief in love after getting left at the altar. Desperate for something to do that will take him away from the wedding scene, he agrees to help his new friend, Julia (Barrymore), plan her wedding to her fiancé Glenn. As they bond, sparks fly, and they both must eventually address the newfound feelings they have for one another.
This film did well enough to set Barrymore and Sandler up to do two more successful films together, and it’s easy to figure out why. The film itself is a true embodiment of the 1980s — from the hairstyles, to the clothes, to the neon pink walls inside Julia’s home. This movie isn’t afraid to poke fun at itself, to say ‘hey, we look silly, but we’re having fun in the meantime’. It also has a truly heartwarming love story, as Julia and Robbie realize what they want from life, and from a partner through each other.
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20. Long Shot
Long Shot is a 2019 romantic comedy starring Charlize Theron and Seth Rogen. When journalist Fred (Rogen) finds himself suddenly unemployed, he has a chance encounter with Charlotte — the girl who used to babysit him, and who also happens to be running for President of the United States. On a whim, Charlotte hires Fred to be her campaign’s speech writer, and the two slowly but surely fall in love.
Although an unlikely duo, Theron and Rogen have excellent chemistry, both romantically and comedically. Rogen’s charm comes from his sense of humor, and Theron plays off it flawlessly — adding a sense of fun and lightheartedness to both their relationship and the tone of the movie. Another highlight of this film is June Diane Raphael’s role as Charlotte’s chief of staff, Maggie. Raphael’s strength as a comedic actor lay in her ability to deliver hilarious lines in a completely deadpan manner, and that skill shines in this film. Overall, this movie is hilarious and shares a unique love story — it’s not one to miss.
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19. Crazy, Stupid, Love
Crazy, Stupid, Love is a romantic comedy that tackles love from many angles. Following several different — but entangled — plots, this film looks at what love is like throughout different phases of life. As Cal Weaver, portrayed by Steve Carell, faces the end of his marriage, his grown up daughter (Emma Stone) begins falling in love with a new man, and his thirteen year old son learns what it’s like to develop an unrequited crush. This movie does a fantastic job of weaving together several separate plots without the details of everyone’s relationships becoming convoluted or confusing.
Carell’s performance stands out, as he plays a leading man struggling to find his charisma after spending his entire adulthood married to his high school sweetheart. Best-known for his role as the not so charming Michael Scott in The Office, it’s pleasantly surprising to see how well Carell can play a man struggling to find himself in the midst of painful heartbreak. At its core, this movie is truly funny, surprising, and heartwarming.
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18. Life As We Know It
Starring Josh Duhamel and Katherine Heigl, Life As We Know It takes a darker approach to romance than most movies in the rom-com genre. Heigl plays Holly, a type A chef who experiences a single bad date with aloof, rebellious Eric (Duhamel) after getting set up by their best friends. Despite vowing to hate each other forever, Holly and Eric have no choice but to join forces when their friends die in a car crash, and they are named the legal guardians of their daughter, Sophie.
Despite the morbid tone the film begins with, the rest of the movie becomes a celebration of what life can be while we are still here to live it. Holly and Eric serve as the perfect foils to one another, and it’s truly fun to watch their relationship — and their respect for one another — develop as they move from merely being co-parents, to friends, to something more. This movie serves as an example that, sometimes, opposites attract for a reason.
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17. Just Go With It
In my opinion, Adam Sandler movies are at their best when Sandler handpicks some of his best friends, finds an idyllic location to shoot at, and turns a movie shoot into a long, paid for vacation. It’s the formula he’s used for films like Grown Ups and 50 First Dates, and it’s the formula he used when developing Just Go With It — a romantic comedy starring him and Jennifer Aniston, taking place on the Hawaiian islands of Maui and Kauai. The best part of movies like these is how contagious the fun the actors are having through the screen becomes; you can sense that the actors are genuinely happy to be there.
Just Go With It is about Danny (Sandler), a plastic surgeon in Los Angeles who wears a wedding ring to convince women he has a neglectful wife, and can then have one night stands without any commitment. That plan works for him until he meets a woman he actually likes — who finds the wedding ring and is repulsed. That’s when he convinces his assistant (Aniston) to pretend to be his wife that he’s divorcing. As the lies spiral out of control, the whole cast of characters wind up on vacation in Hawaii together, and Danny begins to develop feelings for someone other than his new girlfriend.
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16. My Big Fat Greek Wedding
My Big Fat Greek Wedding, starring Nia Vardalos and John Corbett, has been charming its audiences since its debut in 2002. There is nothing inherently complex about the plot of this film. Rather, it’s a simple movie about a hardworking, ambitious young woman named Toula (Vardalos) who falls head over heels in love with a man she meets at work, Ian (Corbett.) There are no grand villains or evil exes scheming against them in this plot — the only trouble they face is her well-meaning, but often overbearing, big Greek family.
The beauty of this movie is that every aspect of it, from the character’s motivations to the conflicts that Toula and Ian face, to the plot itself, is driven by love. Whether it’s Toula’s love for the life she is building, her love for Ian, her love for her family, or her love for her culture, there is no part of this movie that isn’t imbued with an appreciation for life, and the human connections that drive us forward throughout our lives.
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15. The Big Sick
The Big Sick is a 2017 rom-com starring Kumail Nanjiani and Zoe Kazan. Nanjiani and his wife, Emily Gordon, co-wrote the screenplay together. The plot is based on the real life story of how the two met, and the complicated manner in which they fell in love. When Kumail (Najiani) meets Emily (Kazan) after a stand-up comedy show, the two begin a five-month long romance that gets cut short when Kumail refuses to introduce her to his Pakistani-American family, out of fear they’ll reject her for being white. After they break up, Emily falls extremely ill, and Kumail must act as her emergency contact — allowing the hospital to place her in a coma. As Emily remains in a coma throughout most of the movie, Kumail begins to see where he fits in amongst her family, and where he fits into her life.
The Big Sick is unique in the way it tells its love story. Audiences get to watch Kumail experience profound grief while still falling deeply in love with the woman he had just broken up with. The Big Sick doesn’t shy away from the inherent messiness of love, and its embracement of that messiness is what makes it stand out as one of the better rom-coms we’ve seen in recent years.
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14. Never Been Kissed
Out of all the movies on this list, Never Been Kissed has arguably aged the worst. Made in 1999, this film follows nerdy but lovable Josie Gellar (portrayed by Drew Barrymore), who is trying her hardest to prove that she can hack it in the tough world of journalism. After accepting a role as an undercover reporter at her old high school, she haphazardly attempts to fit in with high schoolers as a secret twenty-something — and finds herself clicking most with her English teacher.
Even though Mr. Coulson (Michael Barton) appears tormented by the fact that he’s developing feelings for a girl he believes to be a minor, he doesn’t stop himself from riding carnival rides with Josie; opening up to her about his own lackluster love life, and even asks her to slow dance at prom. The problem is, as a viewer in 2022, audiences can see how fundamentally flawed and inappropriate this relationship is. Yet, the chemistry between Barrymore and Barton is palpable, and somehow leaves you rooting for them as they grow closer and closer. Problematic romance aside, this film is buoyed by its hilarious cast of supporting actors (Molly Shannon, John C. Riley, David Arquette), its quirky representation of 90s fashion, and the fun soundtrack that keeps the movie feeling as lighthearted as its subject matter allows it to be.
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13. Four Weddings and a Funeral
Four Weddings and a Funeral has a unique take on the typical rom-com format. Instead of telling its story in a perfect linear timeline, it follows a group of friends as they attend various weddings — leaving viewers to fill in what’s happened off screen in the chunks of time between weddings, for the most part. Its uncommon method of storytelling makes this rom-com standout amongst its competitors.
Leading man Hugh Grant plays Charles, a man who is perpetually single, doomed to watch his friends marry off and leave him trying — and failing — to charm women at weddings he wishes he could avoid. That is, until he meets a mysterious American woman (Andie MacDowell) who he only seems to run into at the weddings he attends. However, his infatuation with her only partially drives the film forward. The most important relationships in this film exist between the friends who continue to show up for each other, who accompany one another to weddings they hate, and who love each other unconditionally. Their friendships remind viewers that the point of being alive is to love, whether or not it’s in a romantic fashion.
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12. 27 Dresses
27 Dresses, starring Katherine Heigl and James Marsden, examines the complexities of not just romantic love, but of familial love as well. When Jane’s (Heigl) little sister Tess (Malin Åkerman) comes into town and starts dating her boss — who she has been secretly in love with for a long time — Jane’s patience and affection for her sister is tested. Simultaneously, a reporter named Kevin (Marsden) becomes fascinated with Jane and the type of person she must be to have been a bridesmaid twenty–seven times.
While Jane addresses strains in her sibling relationship that she’s been ignoring for years, she also has to contend with the feelings she begins to develop for Kevin — even if he doesn’t act like the kind of guy she even pictured herself with. This movie is fun and poignant, as it tackles what the different kinds of loves in someone’s life can mean to them. If nothing else, 27 Dresses will leave you with a stronger appreciation for Elton John’s “Bennie and the Jets” than you went into the movie with — trust me on that one.
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11. 13 Going on 30
13 Going on 30 is a movie full of iconic moments and references. From the phrase “Thirty, flirty, and thriving”, to the rainbow dress that Jenna wears to her magazine’s party, to the Thriller dance mob, to the fictional Razzles that Jenna and Matty share — there isn’t a moment in this movie that hasn’t cemented itself into pop culture. This film explores what happens when 13-year-old Jenna Rink (Christa B. Allen) wakes up suddenly 30 years old (now portrayed by Jennifer Garner), having achieved all she thought she wanted out of life.
While inherently a very fun movie, this film simultaneously carries a significant amount of gravity. In between the comedic moments of watching a teenager explore life in a 30-year-old body, there is a profound sense of disappointment and fear that accompanies Jenna realizing what she always wanted from life inevitably put her on the wrong path. On that wrong path is the loss of her childhood best friend, Matty, whose adult self is played by Mark Ruffalo. It’s heart wrenching to watch Jenna mourn the consequences of actions she doesn’t remember making, and leaves you rooting for her to return to her teenage self and rectify the path she is about to embark on. While I won’t spoil the ending for you, I will say, this film knows how to tug at your heart strings: prepare some tissues.
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10. 10 Things I Hate About You
10 Things I Hate About You is the perfect rom-com for anyone looking to remember what it was like being an angsty teen. While it is based on Shakespeare’s play “The Taming of the Shrew”, this movie tackles romance in a way that is far less violent towards women, and doesn’t end with its female protagonists appearing tamed by the manipulation and abuse of their husbands. Instead, this movie follows Kat Stratford (Julia Stiles), a teenage girl with a lot of anger towards the patriarchy, and her sister Bianca (Larisa Oleynik), who is mortified by Kat’s reputation and wants to be seen as a traditionally feminine, popular high school girl. In order to meet her single goal of going to prom, Bianca convinces Cameron (Joseph Gordon-Levitt), a boy with a massive crush on her, to pay the school’s bad boy to take her out and convince her to go to prom, as well.
This movie is memorable for so many reasons, one of them being Heath Ledger’s performance as Patrick Varona — the bad boy with a secret heart of gold. Ledger is so charming in this, and reminds audiences of why he was so adored and revered. On top of that, this movie is a perfect teenage time capsule — flawlessly capturing how everything that happens to us as teenagers is felt with a heightened sense of emotions. This movie is the perfect lighthearted rom-com that’ll remind you of when love was a lot simpler.
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9. Forgetting Sarah Marshall
When Peter (Jason Segel) gets his heart shattered by Sarah Marshall (Kristen Bell), the only thing he can think to do is take a vacation to Hawaii in order to escape the memories of their relationship. It’s a great plan until he winds up at the same hotel as Sarah — who is on a trip with her new boyfriend, rock star Aldous Snow (Russel Brand.) Luckily, front desk receptionist Rachel (Mila Kunis) is quick to take pity on him, and befriends him during his time in Hawaii.
First and foremost, this movie is absolutely hilarious. Supporting actors like Russel Brand, Bill Hader, and Paul Rudd make the most of their time on screen, adding layers of humor to the movie that wouldn’t exist without them. Yet, the movie is still driven by its heart, as Rachel and Peter bond and do their best to help heal each other’s wounds. Plus, most of the movie was filmed on location in Hawaii, so the scenery for a majority of the film is gorgeous and vibrant enough to make you feel like you’re on a tropical vacation yourself. You know, minus the earth shattering heartbreak.
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8. 50 First Dates
50 First Dates arguably has one of the wildest concepts for a romantic comedy of the 21st century. After meeting Lucy (Drew Barrymore) at a local café, perpetual bachelor Henry (Adam Sandler) becomes enamored with her, but is warned against pursuing a relationship with Lucy. He learns that after a brutal car accident, Lucy’s short-term memory is permanently damaged, and she is incapable of remembering anything — or anyone — new. Her brain, essentially, is frozen on the date of the accident — meaning she’ll never remember Henry or any date they go on.
Undeterred, Henry dedicates himself to making Lucy fall in love with him every day. Although the plot has a lot of flaws and is deeply unrealistic, the movie still does what rom-coms do best: make you wonder where that kind of love and dedication exists in real life.
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7. Mamma Mia!
If you’re like me, you’ve probably been waiting for someone to discover a way to bottle up the feeling of joy, leaving it accessible to crack open in the midst of bad days. While I haven’t been able to find a vial of pure joy for sale quite yet, I have found Mamma Mia! — and I have to argue that it serves as a close second. Starring Meryl Streep and Amanda Seyfried, this movie musical follows Sophie, a young girl (Seyfried) who finds out through her mom’s old diary that her real dad could be one of three men her mom dated one summer. Determined to find out who her real dad is before her wedding, Sophie invites Bill, Sam, and Harry to the idyllic Greek island where she and her mother reside. But once Donna (her mother) finds the men staying at her inn, old feelings are reignited and chaos (and a lot of ABBA songs) break loose.
Between the shockingly beautiful views of Greece and its oceans, the palpable sense of fun and camaraderie that exists between Donna and her best friends, and the non-stop performances of ABBA’s biggest hits, there’s no way to get through watching this romantic comedy without smiling, and maybe even singing along.
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6. The Proposal
Starring Sandra Bullock and Ryan Reynolds, The Proposal is a masterclass in how to write the perfect combination of heartwarming romance and truly hilarious comedy. This film follows Margaret (Bullock), a publishing executive at the top of her game in New York City, who finds out she is getting deported back to Canada. Instead of accepting defeat, she blackmails her assistant Andrew (Reynolds) into marrying her for a visa. However, the two must sell their feigned love to the DEA agent assigned to their case, and as a result, wind up on a trip to Alaska to meet Andrew’s entire family.
Hilarity ensues as Margaret, an uptight city girl, tries to fit in with his down to earth, and sometimes hippie-ish, family. Yet, in the calm moments between the chaos, Margaret and Andrew begin to see new sides of each other, and their fake love starts to find ground in reality. Additionally, Betty White does a standout job as Andrew’s slightly outrageous, but well-meaning grandmother. Frankly, her performance alone makes the entire film worth it!
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5. When Harry Met Sally
Can men and women ever truly be platonic friends? When Harry Met Sally — arguably the most popular movie in Nora Ephron’s filmography — aims to answer that question by following Harry (Billy Crystal) and Sally’s (Meg Ryan) friendship over the course of twelve years. Despite butting heads when they first meet as fresh college graduates, Harry and Sally continuously cross paths over the course of the next decade, and eventually give in to becoming good friends.
The true magic of When Harry Met Sally comes from the film’s pacing. Instead of watching two people immediately fall in love, audiences get to watch Harry and Sally continuously fall in love with other people, yet still end up back in the company of the other when things inevitably end. Their friendship allows them to see the good, the bad, and the ugly in the other (just pay attention to how Sally orders food) and still choose to love each other. This film is renowned because it does an impeccable job of presenting the possibility that what we all want — someone who will see the dark sides of us, and stay anyway — is out there.
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4. Pretty Woman
Pretty Woman’s place on this list almost doesn’t need an explanation. Thoroughly cemented by viewers and critics alike as rom-com gold, this movie will forever be revered as the standard of what a romantic comedy can be. Julia Roberts plays Vivian, a prostitute in Hollywood who encounters Richard Genre’s Edward, a rich and emotionally closed off business man in desperate need of instructions to Beverly Hills. After Vivian’s guidance charms Edward enough to make him invite her inside, they strike a deal: she will be his pretend girlfriend at important business events for the next six days, and she’ll get $3,000 and a new wardrobe. Of course, their feigned romance elicits sparks of something real, and audience members get to watch the two fall in love.
An always winning rom-com formula is when person A is a loud, goofy, optimistic person, while person B is quiet, reserved, and can’t help but admire person A’s zest for life. Roberts and Gere perfectly embody this golden trope, showing audiences how people operating on two completely different levels can find a way to meet in the middle when they love each other enough. If none of that sounds enticing, just watch it for the shopping spree scene — you won’t think it’s a big mistake.
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3. Bridget Jones’s Diary
As soon as it hit theaters in 2001, Bridget Jones’s Diary became an instant rom-com classic, and for good reason. The film — which is based on a novel of the same title by Helen Fielding, which also happens to be a modern retelling of Jane Austen’s Pride and Prejudice –– follows the klutzy, awkward Bridget Jones as she stumbles through life at 32. Jones is single, lonely, and convinced she’ll die alone. Enter the charming, playboy-esque Daniel Cleaver (Hugh Grant) who shows a sudden and fervent interest in Bridget, alongside Mark Darcy (Colin Firth), a quiet lawyer whose path keeps crossing Bridget’s — and who happens to be better at pining from afar than speaking about his feelings. One Bridget Jones plus two charming, attractive men equals the perfect amount of chaos for viewers to enjoy as she tries to navigate the dating world.
While this film is primarily about romantic love, it also does a beautiful job at showing the necessity of Bridget learning to love herself along the way, just as she is. From the chemistry the entire cast has with one another, to the genuinely funny way Bridget relates to the world, to the brilliant one-liners that make you realize how you want to be loved, this movie is truly a perfect rom-com.
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2. Leap Year
Starring Amy Adams and Matthew Goode, Leap Year is a criminally underrated rom-com that effectively embraces all the tropes of its genre without feeling trite. The film follows Anna (Adams), a high maintenance New Yorker who decides to embrace a Celtic tradition that says women can propose to men on leap day, and ventures overseas to propose to her boyfriend — who just so happens to be in Ireland for a conference on February 29th. Naturally, her travel plans go awry and she finds herself stranded in Ireland — far from her original destination of Dublin — forcing her to rely on Declan — the brute, grumpy pub owner (Goode) she’s just met — to get her to Dublin on time for the leap year.
If you’re someone who loves the optimism and, let’s face it, cheesiness that rom-coms are known for embedding in their plots, this movie is for you. It’s not trying to be nuanced, and it’s not trying to introduce you to a way of thinking. No, its only goal is trying to get you to embrace the joy that comes from watching two polar opposite personalities find what they have in common, and fall in love with each other for it. And if that doesn’t sound appealing to you, maybe just check it out for the evergreen, ever gorgeous hills of Ireland that exist in the background of the whole movie. Trust me, you’ll be checking flight prices before the credits even roll.
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1. Notting Hill
Notting Hill is everything a rom-com should be, and more. It has a perfect meet-cute (after all, who wouldn’t want Hugh Grant to clumsily spill orange juice on them?), a cast of characters that are larger than life — Grant’s bumbling yet hilarious roommate, portrayed by Rhys Ifans, stands out as one of the best side characters in rom-com history — and an iconic scene that everyone has probably heard referenced, whether they’ve seen the film or not (she’s just a girl, standing in front of a boy, asking him to love her, you guys.)
Grant portrays William, an awkward bookshop owner who falls madly in love with Anna Scott (Julia Roberts), a world famous actress. While William’s life is small, revolving around his business and his core group of friends, Anna’s life is too big for her to manage alone — as she isn’t just a person, she’s an icon, a representation of Hollywood and all its glamor. When William becomes the only one to see through the haze of stardom and loves for Anna for who she truly is, Anna must choose what she values most in her life. Their love story, with all its ups and downs, is told beautifully. It will leave you with a little more hope for humanity than when you started.
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