Top 10 Romance Movie Characters Who Picked the Wrong Guy
#10: Andy Sachs "The Devil Wears Prada" (2006)
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While romance isn’t the main focus of this fashion-oriented film, the romantic subplot about Andy’s relationship with her boyfriend, Nate, is a significant one. As Andy’s career takes over her life more and more, Nate seems intent on holding her back. At first, this is a fair move, considering the fact that she doesn’t exactly seem to be treated well in her workplace, but as the plot progresses, Andy’s job clearly becomes important to her. It’s not a good look to question your partner’s career aspirations when they’re committed to their work, and while Andy does eventually make the decision to leave that world behind, it should have been entirely hers to make.
#9: Erica Barry “Something’s Gotta Give” (2003)
Keanu Reeves has experienced a major resurgence in popularity in recent years, but he was still pretty desirable back in 2003 as well. So when Diane Keaton’s character, Erica, ends up choosing Harry (played by Jack Nicholson) instead, it’s baffling. Reeves portrays a young and attractive doctor who has a massive crush on Erica, while Harry is pretty much a vaguely misogynistic jerk. Of course, it’s clear where Erica’s true affections really stand, but we still think she could have lived happily ever after with a man who truly worshipped her and knew how to treat her from the get-go.
#8: Cher Horowitz "Clueless" (1995)
A trope present in so many romantic comedies is the dynamic of enemies eventually becoming lovers. Josh and Cher start off antagonistic towards one another in their roles as ex-step-siblings, which isn’t exactly the ideal circumstance for romance to bloom, right? So while their rapport ends up being a much sweeter one, we still feel like Cher probably could have done better if she’d looked a little further outside of her usual circle… or her own home, for that matter. Sure, Josh helps ground her, but it does seem that on some level he doesn’t truly understand who she is.
#7: Rachel “Something Borrowed” (2011)
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As far as rom-coms go, “Something Borrowed” is a pretty controversial story (and let us just say: it’s even more complicated in the book and its sequel). Anyway, the movie starts off with Rachel sleeping with her best friend’s fiance, so it would be easy to hate her from the beginning. But of course the plot is much more complex than that, and we find ourselves sympathizing with her instead. Regardless though, Dex isn’t the strong character we wish he was. In fact, we kind of prefer Rachel’s dynamic with her friend Ethan (played charmingly by John Krasinski) and could imagine the two of them entering into a more romantic relationship instead.
#6: Mary Fiore (FYORE-ay) “The Wedding Planner” (2001)
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Another rom-com that involves cheating is “The Wedding Planner”. Despite the fact that he’s engaged, Steve finds himself falling for his wedding planner, Mary. While Mary shares his feelings, she’s also in the process of being set up by her father with a man named Massimo (MASS-IH-moh). Though she’s not actually interested in him, Massimo clearly has a heart of gold and seems like he would treat her well. But she ends up leaving him at the altar in favor of running off with Steve.
#5: Mia Dolan “La La Land” (2016)
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Is there any modern romance movie that ends as lamentably as this one? “La La Land” is full of technicolor fun, but by its conclusion we learn that Mia and Sebastian have gone their separate ways in a tragic montage that shows us what could have been, and then gives us the reality of the situation. The two artists weren’t able to reconcile following their individual dreams with making their relationship work, but there was clearly so much love between them that we desperately wish they had tried a little harder. Mia ends up making a safe choice and succeeds in her career, but the audience knows what she could have had.
#4: Anastasia "Ana" Steele (anne-uh) “Fifty Shades of Grey” (2015)
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Much has been written about the more problematic aspects of the “Fifty Shades of Grey” franchise in reference to both the novels and the film series. While notions of BDSM relationships are certainly complex, there are many signs in this story that the arrangement that Ana enters into with Christian is borderline abusive. The biggest issues take place outside the bedroom (or red room in this case) where Christian is controlling and domineering. While we appreciate Ana exploring her sexuality, she could have done it with someone who regarded her as more of an equal.
#3: Andie Walsh “Pretty In Pink” (1986)
Throughout “Pretty in Pink,” a love triangle unfolds between Andie, pretty guy Blane, and Duckie, her best friend who, unbeknownst to her, has a big crush on her. Now, we’re going on record saying she’s better off with neither. Blane continually makes Andie feel ashamed of who she is, and like he cares more about how his friends will react than having the courage to like her. Duckie doesn’t acknowledge that all Andie’s ever wanted was to be friends - even if he did a noble thing by stepping in to take her to the prom when Blane bails. Sorry, dude, just because you tell people you’re the nice guy doesn’t mean Andie owes you a relationship.
#2: Lara Jean Covey “To All the Boys: P.S. I Still Love You” (2020)
In the first “To All the Boys” we (and the rest of the Internet) fell for Peter and Lara Jean’s romance. But although their chemistry is evident, the problems they faced in the sequel made us think that Lara Jean should have considered John Ambrose instead. Hear us out: we know that Peter and Lara Jean are clearly supposed to be endgame, but their communication problems seem to have gotten worse rather than better the longer they dated. John Ambrose is sweet and sensitive, but of course you can’t manufacture a feeling of affection and clearly Lara Jean always has someone else on her mind. Before we unveil our top pick, here are a few honorable mentions. Elle Evans; She Should Have Gone with Marco, Not Noah! “The Kissing Booth 2” (2020) Kathleen Kelly; Joe Essentially Catfishes Her the Whole Movie “You've Got Mail” (1998) Lelaina Pierce (luh-LANE-uh); Neither Michael or Troy Really “Got” Her “Reality Bites” (1994) Daisy Buchanan; Gatsby Was Obsessed with Her, Tom Wanted to Control Her “The Great Gatsby” (2013)
#1: Sandy Olsson “Grease” (1978)
Ok don’t get us wrong, we love “Grease”. It’s an iconic musical for good reason, but with some distance, we realize that Sandy probably shouldn’t have given Danny a second chance. He’s unwilling to be open about his feelings for her for fear of seeming uncool, and he even lies to his buddies about their time at the beach. He also makes a pass at her at the drive in when that’s clearly not the vibe she’s giving off. In the end they both decide to change in order to be together, but from a modern perspective, it’s tough to condone this relationship. Was Tom really so bad?
