Top 10 romance movie characters who picked the wrong guy

play article
Subscribers can listen to this article

This list looks at movie characters who didn't exactly make the best decisions when it comes to their significant others. 

10. Andy Sachs - The Devil Wears Prada (2006)

While romance isn't the main subject of this fashion-oriented film, the romantic sub-plot 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 could be considered a fair move because she doesn't seem to be treated well at her workplace but as the plot progresses Andy's job clearly becomes important to her. 

READ MORE: 8 women filmmakers who've given us stories and roles that have never been seen before 

It's not a good look to question your partner's career aspirations when they are committed to their work. While Andy does eventually make the decision to leave that world behind, it should've entirely been 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 pretty desirable is 2003 as well. So when Diane Keaton's character Erica end up choosing Harry played by Jack Nicholson it's baffling. Keanu 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've 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. Cher and Josh start off antagonistic towards one another in their roles as ex-step siblings - which isn't exactly the ideal circumstance for romance to bloom. While their rapport ends up being a much sweeter one, Cher probably could've done much better if she just 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 on some level he doesn't truly understand who she is. 

READ MORE: Black women in film: Chi Mhende talks to us about what representation means in the African context 

7. Rachel - Something Borrowed (2011)

As far as romcoms go, Something Borrowed is a pretty controversial story. Needles to say, it's even more controversial in the book and its sequel. The movie starts off with Rachel sleeping with her best friend's fiancé so it would be easy to dislike her from the beginning but of course the plot is much more complex than that and we find ourselves sympathising with her instead. Regardless though, Dex isn't the strong character we wish he was. In fact, her dynamic with her friend Ethan played charmingly by John Krasinski is much more preferable. 

6. Mary Fiore - The Wedding Planner (2001)

Another romcom 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 these feelings, she's also in the process of being set up by her father with a man named Massimo. 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 favour of running off with Steve. 

5. Mia Dolan - La La Land (2016)

Is there any modern romance movie that ends as lamentedly as this one? La La Land is full of technicolour fun but by its conclusion we learn that Mia and Sabastian 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 tried a little harder. Mia ends up making a safe choice and succeeds in her career but the audience knows what she could've had. 

READ MORE: Florence Pugh’s 14kg silk flower dress from Midsommar film auctioned for over R1 000 000 

4. Anastasia "Ana" Steele - Fifty Shades of Grey (2015)

Much has been written about the more problematic aspects of the Fifty Shades of Grey franchise in reference to both the novels and film series. While notions of BDSM relationships are certainly complex, there are many signs in this story that the arrangement that Ana enters to 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've 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 better off with neither. Blane continuously makes Andie feel ashamed of who she is and like her cared more about how his friends will react than having the courage to like her. Duckie doesn't acknowledge that all Andie ever wanted was to be friends, even if he did do 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 it doesn't mean Andie owes you a relationship. 

READ MORE: 5 types of women you'll see in The Kissing Booth 2 on Netflix this weekend 

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 Lara Jean and Peter's romance but although their chemistry is evident, problems they faced in the sequel made us thing Lara Jean should've considered John Ambrose instead. We knew that Lara Jean and Peter are supposed to be endgame but their communication problems seem to have gotten worse rather than better the longer they dated. John Ambrose is sweet of course you can't manufacture a feeling of affection and clearly Lara Jean always has someone else on her mind. 

1. Sandy Olsson - Grease (1978)

Grease is an iconic musical for good reason but with some distance we realise that probably should not have given Danny a second chance. He's unwilling to open up 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 in 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. 

Compiled by Phelokazi Mbude

Follow us on social media: FacebookTwitterInstagram

Sign up to W24’s newsletters so you don't miss out on any of our stories and giveaway.

We live in a world where facts and fiction get blurred
In times of uncertainty you need journalism you can trust. For 14 free days, you can have access to a world of in-depth analyses, investigative journalism, top opinions and a range of features. Journalism strengthens democracy. Invest in the future today. Thereafter you will be billed R75 per month. You can cancel anytime and if you cancel within 14 days you won't be billed. 
Subscribe to News24