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Romantic Movie Characters Who Chose The Wrong Guy

Props to these characters for bravely and blindly following their hearts. With that said, they definitely missed (or dismissed) some major red flags along the way.
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Love is blind, as they say. So it’s not farfetched that movie characters can make foggy romantic decisions, sometimes mistaking the wrong one for “the one.”

Some put so much energy into the romanticized object of their affection that they overlook objectively better matches right in front of them. Others seem to think their practically perfect match is “too good to be true,” dumping them out of fear before giving things a fair chance. And of course, others go with the safest best.

The heart wants what it wants, I guess.

Still, just because these romantic movie characters threw caution to the wind in the name of love, that doesn’t mean they found their happily ever after. Think about it this way: if these fictional people are meant to be like real-life people in real-life relationships, they’re going to make real mistakes. But that’s all a part of the journey. In matters of the heart, it’s not always about choosing the “right” or “wrong” person, anyway. The real challenge is choosing the path (or person) that’s better for us rather than the worst. And if you ask me, these love-blind characters did not choose so wisely.

So let’s take off the rose-tinted glasses on their behalf, shall we?

Erica Barry in ‘Something’s Gotta Give’

To tell you the truth, I go back and forth with this one. As their relationship evolves from detesting one another to falling in love, the dynamic between Diane Keaton’s character and Jack Nicholson’s character becomes endearing. And I do believe the love they cultivate is real.

Erica and Harry having a dinner during a thunder storm in Something's Gotta Give
Warner Bros./Columbia Pictures

Still, it’s hard to overlook the potential partner perfection that is Keanu Reeves’ character in Something’s Gotta Give. But Erica couldn’t overlook their age difference before it even began. In this 2003 rom-com, Erica Barry goes with her gut in the end, choosing her twenty-something daughter’s boyfriend who is much closer to Erica’s age. Even the daughter sees what’s between them and lets her beau go.

After everything we witness, Erica choosing Harry is a bit mind-boggling. Harry is a guarded, misogynistic, womanizer, who doesn’t appreciate Erica until she practically saves his life. Keanu’s character is sweet, attentive, understanding, and sees how special she is from the start. They have a wonderful time together and gradually grow closer, but the age difference makes her hesitant and consistently unable to relax.

Warner Bros./Columbia Pictures

No matter who was really “the one” for her, when it comes to treating Erica the way she deserves to be treated, Nicholson’s character can’t hold a candle to Reeves’ charms for 90 percent of the movie.

Mia in ‘La La Land’

In La La Land, we learn that Mia and Sabastian have chosen to go their separate ways in a stunningly painful montage. They’re not the first two people to choose their careers over love. In the end, they achieved the things they set out to achieve, but we all really wanted them to end up together. And I think we all know that’s what they wanted too. I’ll never be over the moment we’re shown all the things that could’ve been. And I’m not convinced they had to lose each other to achieve their dreams.

Mia says "I'm always going to love you" in La La Land
Summit Entertainment/Black Label Media/Gilbert Films/Marc Platt Productions

I realize that no matter how much two people love each other, sometimes they just can’t work it out. La La Land highlights the sacrifices that dreams sometimes require, including ending a magical relationship when the going gets tough and the future is unknown. We will never stop wishing that these two would’ve found a way to reconcile and still pursue stardom.

Still, the audience knows what could’ve been. The ending montage is tinged with regret, and now we all have to live with it.

Summit Entertainment/Black Label Media/Gilbert Films

Andy Walsh in ‘Pretty in Pink’

This iconic Molly Ringwald flick has left audiences wondering if the leading lady made the right decision since 1986. Andy, dreamy-eyed Blane, and Andy’s best friend Duckie are all blind in different ways. Most obviously, Andy is fixated on Blane and seems completely oblivious to her BFF’s crush on her. With that said, we’re not saying Ducky was the better choice. But maybe he was. After all, Andy ended up with Duckie in the original ending before it was scrapped.

In Pretty in Pink, Blane often makes Andie feel lesser. She has to work for his affection much more than she arguably should, and he often seems ashamed to have those feelings at all. While Blane’s into her, he’s more into his image and concerned with what others think, which comes off as cowardly.

Andy and Blane fighting against lockers in Pretty in Pink
Paramount Pictures

Duckie seems unable to accept that all Andy sees him as is a friend. And being a nice guy doesn’t automatically make him the guy for her. The ending being changed suggests that things could’ve or should’ve gone differently. Ironically, if only the test audience hadn’t “booed” the idea of Andy and Duckie coupling up, they might’ve gotten together.

Andy and Duckie at prom
Paramount Pictures

Anastasia Steel in ’50 Shades of Grey’

From start to finish, it’s all about pleasing Christian. The interactions between Ana and Christian feel hollow, delusional, and strangely loveless. He’s the bossiest boss in their professional and personal relationship in the absolute worst ways.

At first, she refuses to sign their, um, their love contract, but later acquiesces in hopes of getting closer. They inevitably take their relationship to the next level (a.k.a. a glamourized form of borderline abuse and ongoing emotional distance). And for what? There are plenty of people Ana could’ve explored her sexuality with. Would they have been handsome, troubled billionaires? I don’t know. But the majority of them wouldn’t have made her sign paperwork and then whipped her, I’m sure. So maybe she didn’t think things through.

Anastasia tells Christan she needs time to think in 50 Shades of Grey
Focus Features/Trigger Street Productions

Since the 50 Shades franchise blew up, there continues to be an ongoing discussion about the more problematic aspects of Christian and Ana’s relationships. Love might’ve been present, but there’s no denying that Christian is controlling and does not view or treat Anastasia as his equal. Sadly, Ana is eternally desperate to please and understand him, even if it means going against everything she actually wants or needs in return.

Focus Features/Trigger Street Productions

Lelaina “Leiny” Pierce in ‘Reality Bites’

The love triangle in Reality Bites is another case of everyone potentially being better off alone. Winona Ryder’s character didn’t necessarily make a mistake by dating Ben Stiller’s yuppie character over brooding Ethan Hawke’s character. But Michael (Stiller) clearly wasn’t the guy for her. As things got complicated, it seemed Lelaina was torn. If she really didn’t know who to choose, maybe her best course of action was to choose neither of them.

Regardless, going with the guy that confesses he’s in love with her for the first time… then cruelly follows it up with “is that what you want to hear? Don’t flatter yourself, sweetheart,” might not be the guy. Just sayin’.

Troy holding Leilana's face in Reality Bites
Jersey Films

Leiny and Troy have undeniable chemistry, but their relationship isn’t the healthiest. Arguably, it borders on toxic. The 90s cult classic has that “will they or won’t they” energy, but their push and pull mostly exists because they’re consistently at each other’s throats, playing mind games, and hesitating to act on their feelings. Over the years, we’ve decided it was sexual tension and longing. Any alternatives would make their feuding much less romantic. But pay close attention the next time you watch this one and you’ll likely see what I mean.

Being challenged is not a bad thing, but they were wise to be hesitant here. Yes, Troy and Leilaina needed their moment (even though she was cheating on her BF to have it). After they give in to their feelings, she doesn’t immediately end things with her boyfriend. So what gives? As I see it, Lelaina was always looking for something (or someone) else, and maybe she was too caught up in both relationships to realize it.

Jersey Films

Sandy Olsson in ‘Grease’

Grease will always be my favorite musical movie about how completely changing who you are overnight can save your relationship. To be honest, I don’t think Danny and Sandy chose the “wrong” person. But there were better ways to go about choosing each other.

Do I root for them? Obviously. Would I prefer their bond to be like it was on those summer nights? Who wouldn’t? The problem is, they both let what others think influence their relationship too heavily. If they were destined to fly into the sky in a hotrod fueled by love, why wasn’t it possible to get there by being true to themselves?

Sandy at pep rally in Grease asking "what happened to the Danny Zuko I met at the beach"
Paramount Pictures

To win over the one she’s hopelessly devoted to, Sandy chooses to become socially acceptable by his cool circle’s standards. Seemingly overnight, Sandy evolves from the modest, sweet, yet spunky “Sandra D.” into a breathy, smoking hot (and cigarette smoking) sexpot donning black leather pants so tight they actually had to be sewn on. Suddenly a woman that could give any man multiplying chills, Sandy’s “transformed” and Danny’s psyched. But didn’t he always love her? Prior to the big reveal, he not so discreetly downplayed his feelings for the sake of his reputation.

In Danny’s defense, he took up sports and earned his letterman jacket to show her how he changed. But the second he laid eyes on the new and “improved” Sandy, he took that thing off, twirled it around, and threw it in the dirt. Progress, schmogress! After months of being true to herself, Sandy evolved entirely in Danny’s direction so he didn’t have to budge. I won’t lie, it was a fun ride. But it definitely could’ve been a more honest one.

Paramount Pictures