Top 10 Darkest Moments in Rom-Coms

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Top 10 Darkest Moments in Rom-Coms

VOICE OVER: Samantha Clinch WRITTEN BY: Francesca LaMantia
Rom-Coms are usually lighthearted, but that doesn't mean they can't have dark moments. Our countdown includes "Never Been Kissed," "Sliding Doors," "Sex and the City," and more!
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Top 10 Darkest Moments in Rom-Coms


Welcome to MsMojo, and today we’re counting down our picks for the Top 10 Darkest Moments in Rom-Coms.

For this list, we’ll be looking at some of the saddest moments in otherwise happy romantic comedies. If you haven’t seen these movies, a spoiler alert is in effect.

Did we miss a particularly messed up rom-com moment? Let us know in the comments.

#10: Karen Finds Out
“Love Actually” (2003)


Most of the characters in this movie get happy endings, but, unfortunately, Karen’s story doesn’t have the same yuletide magic. Karen finds a necklace her husband Harry has hidden, which she naturally assumes is a Christmas present intended for her. But on Christmas Eve she gets another gift altogether, and she realizes that the necklace is actually for someone else: Harry’s secretary. The scene is heartbreaking as Karen goes from elation to subdued devastation. She cries alone in her room, and then pulls herself back together for the kids. Karen deserved better.

#9: Axe Fight
“So I Married an Axe Murderer” (1993)


This movie plays with heavy and lighthearted subject matter throughout. But when it reaches the climactic axe fight towards the end, things get real dark. It essentially goes from a quirky rom-com to a straight-up horror film, as Charlie’s fears about a serial killer are proven justified, even if it’s not whom he expected. Our hero runs away from the madwoman while his friend tries desperately to save him, resulting in a dramatic rooftop showdown. It might seem like a sharp turn, but thankfully the movie manages to temper the more disturbing elements with its macabre sense of humor.

#8: Steve Reveals He Cheated
“Sex and the City” (2008)


This isn’t the only shocking development of the first movie, but it definitely hits hard. Steve was always such a kind human being, and he really was good for Miranda. So when he reveals that he cheated on her it isn’t just shocking, it’s absolutely crushing. Due to her work schedule, Miranda and Steve had stopped having sex, but he never even tried to talk to her about it, at least not that we saw. He just went on and found someone else! For fans of the show, this was a completely out-of-character moment for Steve.

#7: Erin’s Dark Thoughts
“What Women Want” (2000)


Nick thought it was all fun and games being able to hear what women in his life were thinking. But things take an unexpectedly dark turn when he learns what’s truly going on in the mind of Erin, an overlooked coworker. Though any feeling person would be able to tell she’s in distress, it takes Nick’s power for him to realize just how close to the edge she is. Thankfully, Nick stops taking advantage of his newfound gift and uses it to do some good, rectifying his past mistreatment of her. We never figured anything too dark would actually happen, but the suggestion of it is definitely jarring.

#6: Ben’s Affair
“He’s Just Not That Into You” (2009)


Ben is just the worst. He lies to his wife Janine; he smokes behind her back; he constantly talks about how much he hates his marriage; and he cheats on her for no reason. And when she tries to make things better between them, he hides his girlfriend Anna in the closet while they “reconcile”. It’s pretty clear that in all these situations, he’s only really thinking about himself - and not what he’s putting everyone else through. In summation, he deserved to be dumped by both of them when they each came to their senses.

#5: Losing the Baby
“What to Expect When You’re Expecting” (2012)


Most of the baby-centric storylines in this movie are humorous, but they can only be so different from one another before one takes a not-so joyous turn. When Rosie has a one night stand with her high school crush, Marco, she ends up getting pregnant. At first neither of them wants this, but they ultimately make the most out of the unexpected situation. Just as they seem to be becoming a truly happy little family, however, Rosie has a miscarriage. We don’t actually hear the words in the scene, but it is somehow worse only seeing Rosie’s reaction in the hospital.

#4: Alternate Timeline
“Sliding Doors” (1998)


This movie is more than just your average rom-com to begin with. It shows two alternate timelines for the main character Helen. In one, things go pretty terribly, but all of those moments seem to be stepping stones toward true happiness. In the other, Helen misses all of those moments and though things seem to be going well, it ends in tragedy. Helen and James profess their love for each other when Helen turns around and is hit by a van. The moment is so sudden and unexpected that it hits you like...well, like a van. Watching Helen die with James by her side when they were just getting started is heart-rending.

#3: Fred’s Death
“Breakfast at Tiffany’s” (1961)


Holly is a pretty happy-go-lucky kind of character. Her name is Holly Golightly for crying out loud. She concerns herself with the excesses of life and dreams of marrying a rich man and taking care of her brother Fred upon his return from war. Suffice it to say, Holly generally has a chipper disposition. But things change when Holly suddenly learns Fred died. When Holly finds out, she breaks down and destroys her apartment out of anger and desperation. Seeing her go from such high highs to such low lows is enough to wrench your heart right out of your chest.

#2: Billy Prince’s Prank
“Never Been Kissed” (1999)


Copy editor Josie Geller gets a second chance at a proper high school experience when she goes undercover as a student to write an exposé. Though she can’t seem to escape her old identity as one of the unpopular kids, things do seem to go a bit better this time around. However, she still feels the sting of her worst adolescent experiences. A flashback shows her being humiliated in front of her crush, only for him to ask her to the prom. Her jubilation is so endearing but it all comes crashing down when he shows up with his real date and throws eggs at her. That kind of thing sticks with a person forever.

#1: Vivian’s Assault
“Pretty Woman” (1990)


This movie tells the playful story of a businessman, Edward, hiring a sex worker, Vivian, to pose as his girlfriend to help him land a major deal. Along the way, Vivian gets to see what it’s like to be a “proper lady.” However, while Edward sees past just her profession, his lawyer, Phillip, does not. While alone with Vivian, an angry Phillip tries to force himself on her, believing she’s available to whoever asks. Fortunately, Edward intervenes, but the bluntness of this scene is stark in its real-life horror.
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