The Most Difficult Rom-Com Circumstances

Josh reading while Cher looking over his shoulder
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Some rom-com couples are just so totally clueless. Sure, at their core, rom-coms are all about the laughs and the romance. It's in the title, after all. Yet that doesn't mean the characters don't face intense challenges that would make any relationship difficult. Sometimes, these difficulties stem from the overall dynamic and circumstances of the couple-to-be and other times, they face challenges in their lives that cause more grimaces than grins. Either way, it's always nice to see some depth that distinguishes a rom-com from the typical formula. We're totally buggin' over these difficult rom-com situations.



There's nothing like dealing with an unplanned pregnancy before you start dating the baby's biological father. Juno takes audiences on the journey of a surprise pregnancy after a one-night stand. Though the love story between Juno (Elliot Page) and Paulie (Michael Cera) is both wholesome and a little awkward, the film's real love story is between Jennifer Garner's character Vanessa and her adopted baby. 

In addition to tackling teen pregnancy, the movie also shines a light on predatory behavior and marital problems — showcasing that not every seemingly picture-perfect relationship is as great as it seems. All in all, Juno is both goofy and hard-hitting, striking a balance between comedy and intensity. 



Hey, kids, don't date your ex-stepbrother — unless you're Alicia Silverstone and Paul Rudd. Clueless is undeniably one of the best rom-coms of all time, but the movie still gets flack for the dynamic between Cher and Josh decades after its release. Having a crush on your ex-step bro (and vice versa) isn't exactly the most traditional meet-cute, but even Cher's dad seems to ship his daughter and his ex-wife's son. However, there is that pesky quote from Cher's overworked yet doting father that makes things dicey: "You divorce wives, not children." 

Even though the film heavily implies that Cher and Josh were only step-siblings for a short time when they were younger, Mel still treats him like a family member — making Cher and Josh's eventual coupling a bit muddy. Of course, neither views the other as a sibling, and their parents weren't together long enough to form a genuine sibling bond. It's easy for fans to view their dynamic as sibling-like banter or a flirty repartee. But for the sake of the ending, we'll stick to the premise that they have more of a "friend of the family" romance vibe than a familial one. And there's no denying that they make each other better. Josh brings out Cher's empathetic side while Cher encourages Josh to get out of his shell and enjoy some spontaneity. 


The Proposal

Who doesn't want their relationship to begin with their boss basically extorting them to marry them for a green card? Yet fans can't help rooting for Margaret (Sandra Bullock) and Andrew (Ryan Reynolds) as they go from workplace enemies to lovers. Margaret is not only 12 years older than Andrew, but she's also in a power position over Andrew — and she uses that to her advantage when she promises him a better job in exchange for a quickie marriage. Naturally, it's a pretty shady way to begin what develops into a real relationship.

Margaret does redeem herself by coming clean when she realizes that she is, in fact, in love with Andrew. However, it's still a dicey situation that doesn't convey the best message. As a result, the characters have a lot to work through, and fans have to grapple with the real-life implications of this match. 


She's the Man

What could possibly go wrong in a Shakespearean comedy? Amanda Bynes' 2006 film She's the Man is loosely based on Shakespeare's Twelfth Night, which features the love story between a man and a woman who pretends to be a man to combat sexist bias. For those who need to brush up on their high school English class, think Mulan — but with soccer.

Bynes' character Viola takes on the identity of a boy and enrolls in a school with an elite soccer team to prove that women are just as athletic (and more so in some cases) as men. While undercover, she falls for a classmate named Duke (Channing Tatum), but Laura Ramsey's character Olivia falls for Viola. Of course, hijinks ensue. On top of being an intensely complicated premise for a meet-cute, the original play and the film are a wonderful depiction of the fluidity of attraction and gender identity. There's also the fascinating undertone of the fact that back in Shakespeare's day, men performed all acting roles in theatre. 


Palm Springs

Let's do the Time Warp again. Okay, so Palm Springs isn't the first film to take on a Groundhog Day premise. The fact that the trope is basically named after the '90s film is a testament to that. Yet many films that rely on this premise only have one character dealing with the endless repetition of a single day. Alternatively, Palm Springs features two characters — Nyles (Andy Samberg) and Sarah (Cristin Milioti) — embarking on their time loop journey together. 

Imagine going through the monotony of the same wedding every day for the foreseeable future. That's what Nyles and Sarah have to contend with. Even with the Palm Springs setting, that would get tiring fast. Like most time loop films, both characters have to learn lessons amidst their wild adventures stemming from the lack of consequences when you live the same day repeatedly. However, the film has a big twist that most of these movies lack, along with more than a few intense moments. 


Mr. and Mrs. Smith

Ah, the beginning of Brangelina (and corny ship names as a whole). Keeping your status as an assassin from your spouse is one thing. It's quite another for both parties of a marriage to keep their day jobs a secret — especially when they're working for rival assassin companies. It's pretty awkward to discover that your husband (and wife) is actually your workplace nemesis, but them's the breaks in the assassin game. 

Though their work and home life have a life-or-death component that sets the film apart from other rom-coms, there's still plenty of humor in the rather absurd situation that John and Jane (clearly named after unidentified bodies) find themselves in. If only their last name was Doe. While the movie borders on action, at its heart, the film is a rom-com masked as an action flick, offering something for everyone. 


13 Going on 30

Being 30 isn't all it's cracked up to be when you age nearly two decades in the span of a second. In 13 Going on 30, Jenna Rink is your average 13-year-old: desperate to grow up, finish puberty, and fit in with the popular girls. So, when she wishes to turn 30 after realizing that her BFF Matt is in her closet to play seven minutes in heaven instead of her crush, she's devastated. You'd think that wishing dust would be just that — a wish — but Matt's magical dust allows Jenna to skip nearly 20 years of her life to reach the coveted three-oh. 

Unfortunately for Jenna (Jennifer Garner), the aged-up teen doesn't realize that she's in love with Matt (Mark Ruffalo) until it's too late, and he's set to marry someone else. The age issue is a bit icky at times, and Matt's charm subsides a bit with the whole cheating thing, but the two manage to have some pretty heartfelt moments amidst their bizarre circumstances. 


Midnight in Paris

Okay, so we've had time jumps and time loops, but what about time travel? Midnight in Paris is a pretty bonkers ride from start to finish. Owen Wilson plays Gil: a down-on-his-luck writer with a materialistic fiancée who isn't keen on living the starving artist life. Naturally, he time travels to the 1920s by hanging out on the streets of Paris at midnight, when he gets carted off to various decades throughout time.

The mechanics of the movie's time travel component are never quite clear, though it appears to show up when someone needs it the most. On top of the challenging concept of falling in love with someone in a different time period, Midnight in Paris deep dives into the notion of unsatisfied people looking to the past as the "golden age" rather than living in the present. It's certainly fun to see a slew of onscreen depictions of famous artists, writers, and historical figures. But the film also focuses on multiple main love interests — and falling in love more than once — which is something we rarely see in romantic comedies. Sure, plenty feature several romantic possibilities, but there's usually a headliner that's the obvious winner from the start. As a result of the film's whimsy in relationships and time. Midnight in Paris takes fans on just as much of a journey as Gil. 

Looking for a rom-com? Love Again premieres in theatres on May 5! See it at Regal. 

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