However, when a romantic comedy movie gets those heartbreaking scenes right, those moments can often be the most evocative. Sometimes, making the audience feel the opposite of how they thought they’d feel is a move that can bring a visceral edge that makes the rest of the film far more emotionally resonant. It turns a movie that may have initially appeared shallow into something much deeper. Which moments in the romantic comedy genre have had the hardest impact on viewers? Which movies successfully delivered crushing blows to the audience, despite their overall comedic tone? Here are our picks for the saddest scenes in romantic comedy movies throughout history and how they did it right.
8. Emily Is Sick (The Big Sick)
The Big Sick tells the true story of how comedian Kumail Nanjiani met his wife Emily. Far from the usual clichés, Emily ended up in the hospital—after they’d been dating for only a few months—due to an auto-immune disease that doctors didn’t know about. The scene where the aspiring comedian goes up in front of an audience and breaks down while explaining the fragile condition Emily is in? It’s one of the bravest and most heartbreaking sequences in romantic comedy, with Kumail not knowing what to do about the situation. Nanjiani and Emily wrote the script together, resulting in a delicate and smart story that uses his emotional turmoil to convey hopelessness to the audience while displaying the depth of his feelings for Emily.
7. Helen Leaves Jessica (Kissing Jessica Stein)
Seeing Jessica Stein’s journey from uptight young woman (who’s extraordinarily repressed) to confident gay woman in a relationship with Helen is the earnest heart of Kissing Jessica Stein. Jessica learns to accept the love she has for Helen, and that process dominates the narrative. When they finally end up together, we think the movie might fade out nicely—but it doesn’t last, and Helen leaves Jessica because Jessica is unable to express herself physically. Watching the pair break up is a moment we don’t expect, and the relationship crashes down to stark reality. Jessica sobs tears as Helen packs her things. They aren’t star-crossed lovers after all.
6. I Hate the Way… (10 Things I Hate About You)
As the indomitable Kat Stratford stands up in front of her class, Patrick Verona is sitting there too, unwilling to even look at Kat after the lies he’s told her. She begins reading out her poem. The poem is clearly meant for Patrick, who looks intently at her as she begins to cry while admitting she doesn’t hate him. She’s devastated that he hasn’t called to make things right with her. Kat leaves the room and Patrick is so ashamed of himself for not calling her when he knows he should’ve. The scene is a perfect blend of Kat’s hatred for people and the boy who saw through her icy demeanor. Him making her cry is a moment of fragility for the usually fiery Kat, and it leaves us in bits, too.
5. I’m Also Just a Girl (Notting Hill)
Will Thacker was utterly embarrassed by Anna Scott when he took a trip to see her filming on Hampstead Heath. Now that he’s back at his travel book store, he’s in a delicate mood. He’s saddened by what’s happened between him and Anna, yet also feeling foolish that he thought she could still be in love with him. Then, she appears. She’s holding a gift for him, standing in his doorway in casual attire, looking like any other person walking through Notting Hill. Our hearts share a collective jump as she stands there—but as they begin talking, it’s clear she hurt him. Anna’s picturesque face when he tells her that he can’t be with her is a painful reminder that she’s human. The global megastar is breaking inside because of his rejection, which is when she tells him that she’s “just a girl standing in front of a boy, asking him to love her.” It’s a line that brings us to tears as she loses the man she loves.
4. The Tramp Is Embarrassed (City Lights)
The final scene in City Lights was once described by a film critic as “the most beautiful ever put to celluloid.” That sentiment is hard to argue against, with the final sequence being Charlie Chaplin’s The Tramp finally meeting the blind flower girl who can now see. The ending finds him released from prison, poorer than ever, and walking the streets—when, suddenly, he sees that she’s been cured of her blindness and has even opened a flower store. She offers him a flower and some money, but he tries to leave out of shame for his own poverty. However, she brings him back and holds his hand, realizing that he was the one who cured her blindness. It’s a scene that leaves us elated and crying tears of joy, which are well-deserved after the topsy-turvy film we’ve just watched.
3. Joe Walks Away (Roman Holiday)
The tale of Joe Bradley and Princess Anne’s storied day of enjoying the sights of Rome has become an iconic romantic comedy narrative. The emotional impact of the final scene—as Joe meets Anne as a princess for the first time—is unrivaled by any modern film. When the two see one another again at the press conference for Anne’s visit to Rome, Anne realizes that Joe knew she was a princess all along. He gives her photos of their day together, which she accepts. Having previously expressed that she wouldn’t have returned to the palace if she wasn’t so aware of her duty to her country, Anne leaves Joe standing there as the press filter out. He watches her go—then turns and walks away from somebody he loves, with his dignity intact and head held high, knowing that he’s done the right thing… but it leaves us in tears at the heartbreaking end.
2. Tim Says Goodbye to His Dad (About Time)
About Time might be the romantic story of how Tim meets Mary during his travels through time, the real crux of the tale rests in the relationship that Tim shares with his dad James. Knowing that he can’t travel back in time before the birth of a child—as it could mess up his family life—Tim has to share a final goodbye with his departed dad, who he won’t be able to see once his new baby arrives. While playing one last game of table tennis, Tim lets his dad win. This alerts James to the fact that something is wrong. When Tim tells his dad that his baby is due any hour, James smiles, knowing that his son found happiness. They share a final trip back to when Tim was a boy. The scene is a powerful reminder of the love shared between a father and his son, making us sad that Tim has to say goodbye to his amazing dad.
1. Both Sides Now (Love Actually)
The iconic Christmas romantic comedy from Richard Curtis boasts an ensemble cast of characters who are all loosely connected to one another, with all of them trying to enjoy the festive holiday season. However, when Alan Rickman’s Harry has an affair with a younger woman at work, he leaves Emma Thompson’s Karen devastated when she finds out about her husband’s cheating. On Christmas Eve, she goes into her bedroom—leaving her husband and her children downstairs briefly—and cries while listening to Joni Mitchell’s “Both Sides Now.” The scene is a blow to us watching, as we all stand in that room with Karen and sharing in her feelings of betrayal. What makes it all worse is that she has to compose herself and go back downstairs, pretending nothing has happened so as not to ruin her family’s Christmas. Karen’s heartbreak is universal, but that need to compose herself and return to her family adds a dimension to the scene that gives it an emotional heft unusual for a romantic comedy. Read next: The best Valentine’s Day movies for couples
