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VOICE OVER: Kirsten Ria Squibb WRITTEN BY: B Stevenson
Man, why did these couples have to break up? For this list, we'll be looking at romantic pairings in films who experienced a truly regrettable split. Our countdown includes "Prime," "Becoming Jane," "Casablanca," and more!

#10: Raffaela “Rafi” Gardet & David Bloomberg “Prime” (2005)

In this romantic comedy-drama, Rafi, an ambitious woman in her late thirties, becomes involved with a naive but charming painter 14 years her junior. As Rafi’s therapist, Lisa hears of the relationship, but then learns that the boyfriend in question is Lisa’s own son. This conflict of interest stirs up its fair share of drama, but Lisa eventually comes around. In fact, although the painter, David, says he’s ready to have the child that Rafi wants, it’s the latter who decides that he shouldn’t make that big of a sacrifice. With no external obstacles in their way, it’s devastating to see the head-over-heels lovers part ways. When their eyes meet through a windowpane a year later, it isn’t hard to imagine them rekindling their romance.

#9: Elio Perlman & Oliver “Call Me by Your Name” (2017)

This acclaimed film follows a blissful summer in Northern Italy during which 17-year-old Elio falls for visiting graduate student Oliver. Although their flirtation is subtle at first, the pair begin a powerfully romantic fling that honestly ends too soon. After Oliver’s departure, Elio is devastated to hear of his engagement, but he gains a modicum of closure from an emotional phone call. Although this romantic drama thoughtfully examines first love and the heartbreak that it can bring, it’s disappointing that the lovers don’t plan another visit or maintain correspondence. With their intense chemistry, it’s fair to say that the star-crossed couple could have made it work.

#8: Sebastian Valmont & Annette Hargrove “Cruel Intentions” (1999)

A promising romantic pairing meets a truly tragic end in this teen romantic drama. Wealthy step-siblings Sebastian and Kathryn bet on whether the former can seduce Annette, the daughter of their school’s headmaster. But then Sebastian genuinely falls for Annette and wants to tell her the truth, only for Kathryn to persuade him to break up with her - which he reluctantly does. Unfortunately, Sebastian is only able to confess his true feelings at a time of tragedy, in his dying breaths after falling victim to a traffic accident. The couple’s story is hard to swallow, especially as it was only Kathryn’s machinations that caused their suffering. Although Sebastian’s journal acts as a memento for their relationship, it’s still heartbreaking to imagine what could have been.

#7: Gary Grobowski & Brooke Meyers “The Break-Up” (2006)

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Next, we follow a couple who separate but, in an unconventional twist, continue living together. Unfortunately for Gary and Brooke, they each have their gripes, and attempt to get back at one another in somewhat petty ways. But, it soon becomes clear that both parties regret the break-up that brought them to their current situation. Unfortunately, Gary snubs Brooke’s final peace offering, and by the time he gets his act together, his ex-girlfriend has moved on. It’s a painful result, as all that was needed was some more care and compassion. Although neither party bears ill will by the film’s end, we wish they had worked through their problems rather than calling it quits.

#6: Jane Austen & Thomas Lefroy “Becoming Jane” (2007)

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Sometimes, love just isn’t enough. This biographical film dramatizes the celebrated novelist’s youth and her relationship with Tom, an arrogant lawyer. Although they don’t get along at first, the pair eventually fall in love. However, trouble arises when Tom’s rich uncle refuses to give the couple his blessing. With Jane’s family lacking wealth and her lover needing to sustain his own relatives, it becomes clear that their romance just won’t work. It’s truly difficult to watch two people so smitten be separated by circumstance. Perhaps most tragically, Tom is willing to take a leap of faith, but it’s Jane who knows she must end things.

#5: Robert Kincaid & Francesca Johnson “The Bridges of Madison County” (1995)

In a flashback, this emotional romantic drama chronicles a four-day affair between an unhappy housewife in Iowa and a photojournalist covering local infrastructure. While her husband and children are away, Francesca helps the visitor find his photographic subject and, unwittingly, his artistic spark. In the present day, Francesca’s children are shocked to discover mementos of the brief relationship and the sacrifice their late mother made by staying with them. It certainly would have been devastating for Francesca to abandon her family. Even so, we were absolutely rooting for her and Robert.

#4: Rick Blaine & Ilsa Lund “Casablanca” (1942)

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It’s an iconic, World War II-set romance, and one of the most famous in all of cinema, but with a truly bittersweet ending. Rick and the widowed Ilsa began their relationship in France, but she disappeared after learning her husband was actually alive. Later, in the titular Moroccan city, the old flames still have plenty of chemistry —and feelings for eachother. But in the end, Rick ensures that Ilsa and her fugitive spouse can escape to safety in a war-torn world. It’s an honorable act and certainly the right thing to do, but we hate to see the lovers once again pulled apart. They’ll always have Paris… but couldn’t they have had a lasting relationship, too?

#3: Jack Twist & Ennis Del Mar “Brokeback Mountain” (2005)

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This couple doesn’t break up in the traditional sense, as they carry on with infrequent encounters after their initial separation. But, these reunions never reach the heights of the fateful summer they spent together. The pair first meet as cowboys herding sheep on the Wyoming peak and eventually fall in love. However, when the season ends, they split up as if nothing happened. It’s hard to see them hide their obvious longing, knowing the moment could have gone differently. Just as emotional is their reconnection four years later, when their love is out in the open but burdened by marriage and children. It wouldn’t have been easy to build a life together, but do we ever wish they’d given it a shot.

#2: Celeste Martin & Jesse Abrams “Celeste and Jesse Forever” (2012)

Now, this relationship really does have a downright unconventional trajectory. Celeste and Jesse are highschool sweethearts who eventually marry, but then embark on a shockingly amicable separation... attempting to remain friends all the while. Although Celeste initiates the split, she ends up regretting it after her husband moves on. By late in the film, Celeste has accepted that she could have done more to sustain the relationship in the first place. Her remorse over the decision she took is clear, and seeing the BFFs move on from their life-changing union just doesn’t seem to make sense. But sometimes, even truly one-of-a-kind chemistry can’t save a relationship that’s on the way out. Before we unveil our top pick, here are a few honorable mentions. Scott Pilgrim & Knives Chau, “Scott Pilgrim vs. the World” (2010) They’re In Sync — Literally Adèle & Emma, “Blue Is the Warmest Colour” (2013) One Moment of Infidelity Is the Nail in the Coffin For This Passionate Romance Joel Barish & Clementine Kruczynski, “Eternal Sunshine of the Spotless Mind” (2004) Splitting Up Teaches Them That They’ll Always Come Back Together

#1: Sebastian “Seb” Wilder & Mia Dolan “La La Land” (2016)

One’s a jazz pianist, the other is a Hollywood hopeful, and they meet in Los Angeles. As Seb and Mia work on realizing their dreams, the couple begin a life together. Unfortunately, they later break up. But when Seb notifies Mia of a promising audition, it seems like their relationship could be back on. And yet, their paths permanently diverge, seemingly so they can focus on their career aspirations. Was a separation really necessary for their success? One of the film’s final scenes, a montage depicting their hypothetical life together, makes the split even harder to accept. When it comes to imagining an alternate outcome for a beloved pairing, it doesn’t get much easier than this.

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