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Who Was Right? Was It Wrong? Revisiting the Results of Iconic Rom-Coms

Did Tom actually have good reason to be upset in ‘500 Days of Summer’? Was Henry’s pursuit of Lucy in ‘50 First Dates’ ethical? Two Ringer staffers debate the merits of famous plot points—or entire relationships—while a third settles the case once and for all.

Tara Jacoby

When you find the theme week you want to spend the rest of your life with, you want the rest of your life to start as soon as possible. Thankfully, The Ringer hereby dubs this week Rom-Com Week, a celebration of one of the most delightful, captivating genres in film. Head to the top of the Empire State Building, order what she’s having, and join us as we dig into everything the rom-com has had to offer over the years.

So far during The Ringer’s Rom-Com Week, we’ve tackled a couple of contentious topics: What are the genre’s greatest movies? And who are its true icons? The answers can lead—and have led—to conflict, which makes sense. Conflict is a defining characteristic of rom-coms, and it often leads to great debate on the part of the audience. In some films, that debate kicks up from the first viewing. Other times, a discussion emerges much later, after people have had time to reflect on what happened.

500 Days of Summer is a perfect example of the latter (and it’s also the movie that inspired this piece). The film seemingly positions Tom (Joseph Gordon-Levitt) as the clear target of our sympathy, suggesting he was wronged by Summer’s (Zooey Deschanel) refusal to acknowledge their relationship. But in the years after the film’s 2009 release, a new critical consensus emerged: Summer had always been truthful about her intentions; Tom just refused to accept them. To this day, you can find 20-minute-long videos on YouTube debating the merits of both sides of the argument.

With that in mind, we decided to take a look back at several other famous rom-coms and debate which plot points—or entire relationships—have been potentially misunderstood. To examine the cases, I recruited my colleagues Claire McNear and Michael Baumann to argue over a few choice examples, and after careful consideration, I will judge once and for all how we should feel about each subject. Are you ready? Let’s begin with the granddaddy of them all. —Aric Jenkins

500 Days of Summer: Who Was Right, Tom or Summer?

Coworkers Tom and Summer begin dating. Tom, we’re told, is desperate to find “the one,” and he thinks he’s found that in Summer. Summer, meanwhile, insists she doesn’t want to be in a serious relationship, and ultimately dumps Tom.

McNear: Summer Was Right

The single funniest moment of 500 Days of Summer comes most of the way through, when a sad-sack, post-breakup Tom agrees to go on a date with a woman named Alison (Rachel Boston) to try to snap him out of his funk. Instead, Tom spends the evening sulking.

“There’s two options, really,” he slurs at Alison, already a few sheets to the wind. “Either she’s an evil, emotionless, miserable human being, or she’s a robot.”

“Can I ask you a question?” Alison eventually breaks in. “She never cheated on you? She ever steal or take advantage of you in any way? And she told you upfront that she didn’t want a boyfriend?”

No, no, and yes, Tom replies; check and mate. Summer was crystal clear about her wants and needs from the get-go, and when she sensed that they weren’t being met—and they profoundly weren’t, as Tom all but stated his intention to Elmyra her until they both dissolved into ash—she told Tom, kindly but firmly, that it was time for her to move on.

Baumann: Tom Was Right

Tom is fixated on getting Summer to open up and let her guard down, but his entire personality, such as it is, is a set of aesthetic preferences assembled to send a message to … somebody. He’s a millennial who wears sweater vests and Joy Division T-shirts and is into architecture but, like, Beaux-Arts architecture. What a weirdo. The point is, Tom is deeply, profoundly, overridingly insecure. Which doesn’t make his uncertainty and passive-aggressiveness righteous, of course, but at least understandable.

Summer, meanwhile, seems to have built her life around the phrase “I don’t want a serious relationship” while behaving in a fashion that bears only a passing resemblance to her stated values. Their fight after Tom decks the finance bro in the bar ends badly for Tom, who seems to be under the impression he can unilaterally declare them to be in a relationship. That’s too far. But up until he crosses that line, he’s right. Are Summer and Tom dating? Perhaps not, but they’re going on lots of dates. And having sex with each other, but no one else. Is monogamy not monogamy if you lie to yourself about it?

Jenkins: Oh, Tom. I feel for you. If there’s one thing to know while navigating adult dating, it’s that situationships almost never end well. It’s a flawed concept nearly on par with “friends with benefits” in terms of naivety. “We’ll go on actual dates and sleep together for consecutive months but resist genuine feelings because we’re just hanging out.” Yeah, OK.

I’m tempted to side with Tom because Summer inviting him to her party just to flaunt her engagement ring is straight up ridiculous behavior. The only rationalization I can think of for that decision is that showcasing the ring would finally make it clear to Tom that this relationship ain’t happening. And this is why I ultimately have to side with Claire.

Tom’s refusal to accept Summer’s terms by this point of the movie is hard to defend. And Summer technically did nothing wrong during her entanglement with Tom. Part of you thinks, Well, sure, I just wish she had communicated her stance a bit more. Shall we go over that conversation with Alison once again? To Baumann’s point, only the harshest critics could argue Tom wasn’t justified in his sense of uncertainty. But in this romantic comedy court of law, Summer broke no rules. Blame the state of modern dating, not Zooey Deschanel.

Clueless: Is the Romance in Clueless, uh, Romantic?

Cher Horowitz (Alicia Silverstone) is a California teen on a well-meaning but occasionally misguided quest to find love for others—her teachers, her friends, the new girl at school. But she isn’t necessarily looking for a relationship herself, until she finds the boy of her dreams: Josh (Paul Rudd), her ex-stepbrother, home from college and helping out at her dad’s law practice.

Baumann: It’s Not Romantic

You know how I know Paul Rudd is charming and likable? Because his character in Clueless—a college guy whose age is unspecified but advanced enough for him to be helping at his ex-stepfather’s law practice—is scamming on his 16-year-old ex-stepsister … and everyone’s basically OK with it. WHAT?

This isn’t medieval Spain or whatever, this is 1995 in Southern California. These people have computers. Just because nobody in the film freaks out when a high school girl—presumably a sophomore, based on her taking her driving test late in the film—takes up with a college guy she’s related to by marriage doesn’t mean alarm bells shouldn’t go off for us. When you were in high school and someone had a mysterious, much older boyfriend, didn’t that raise a ton of questions? Defend this, Claire. I dare you. I double-dog dare you.

McNear: It Is Romantic

We hold these truths to be self-evident: that Paul Rudd is ageless; that the Merriam-Webster definition of ageless is “not growing old or showing the effects of age”; that one who does not grow old is therefore never not young; that one who is not not-young can simply be deemed “young”; that thusly it is not for you or I or California Penal Code Section 261.5 PC to determine whether Paul Rudd was 16 or some objectively concerning and likely legally actionable age; and, finally, that if the pan-aged Paul Rudd is charming, well-received by his intended, and not led shrieking to jail by officers summoned by the horrified adults tasked with protecting the welfare of the literal child in their midst, that the romance cannot be proved false.

Jenkins: Every year Paul Rudd gets older, and every year we collectively ask, “How?” How is this man [checks notes] 53 years old and winning People Sexiest Man Alive awards? His anti-aging properties are matched only by those of Pharrell and Jennifer Lopez. It’s a sight to behold in the real world.

In the world of Clueless, though, it’s prompting us to make justifications for a romance that is frankly unsettling. And when you combine the age issue with the fact that Rudd’s and Silverstone’s characters are step-siblings, I start to get seriously weirded out. Sure, they might technically be ex-step-siblings, but they still have a familial bond. How do you alter that dynamic in your head? Unless you already thought about your step-sibling like that and … you know what, I’m not even going to get into that. The fact of the matter is that dudes in college who date high school girls are sus; I don’t care if you’re only a freshman—go date a college freshman like yourself. I’m not sure how we missed this when we were younger, but going forward I personally don’t want to see any “romances” like the one in Clueless.

How to Lose a Guy in 10 Days: Who Was More Wrong, Ben or Andie?

Ben (Matthew McConaughey) and Andie (Kate Hudson) begin dating shortly after agreeing to competing dares. Andie is trying to commit as many relationship faux pas as possible to ensure that she is dumped within 10 days. Ben has pledged to get a woman to fall in love with him over the same time period. Neither knows about the other’s ulterior motives.

McNear: Ben

I acknowledge that Andie, our plucky magazine columnist on a mission to get dumped, is very bad. She spends most of the movie actively antagonizing Ben, whereas he, for the most part, simply attempts to grin and bear her antics (in as condescending a way possible, but I digress). Ben does not, for example, pick a fight with a large, angry stranger in a movie theater for the sole purpose of getting said stranger to bequeath a shiner upon his date. Andie has a lot to apologize for.

But while accepting that both Andie and Ben are behaving reprehensibly by stunt-dating in the first place—each is under the belief that the other is an innocent party whose feelings and presumed heartbreak they wholly dismiss—let’s not forget their differing motives. Andie got into this mess to cover for a freshly dumped friend (poor Kathryn Hahn; thank goodness she’s no longer relegated to side plots) after their shared boss ordered the friend to turn her despair into content. Ben, meanwhile, agreed to the dare for the grand purpose of … stealing work from two of his ad agency colleagues, who were already trying to win over the client when he decided to steal the glory for himself. (Ben does this with the blessing of the agency’s older, male boss, who agreed to the gambit shortly after looking down the competing—and yes, female—colleagues’ cleavages, natch.)

And what happens when the stunt blows up in both Andie’s and Ben’s faces? Andie finds that the promotion her editor dangled was BS, forcing her to quit her job, while Ben is lauded for his genius, with his colleagues shoved to the side. Andie’s last column was a public mea culpa. Ben got a promotion.

Baumann: Andie

I mean, who hasn’t done ethically sketchy things to get ahead at work? Like, say, volunteering to defend the problematic protagonist of 500 Days of Summer in a rom-com debate construct.

So I’ll concede that if both our scheming lovebirds had stumbled upon unsuspecting marks, Ben would have been more wrong. Manipulating someone into falling in love is more harmful than being annoying for a week and a half. But they didn’t. So Ben doted and pampered, while Andie violated his boundaries, embarrassed him in public, and bought him a dog. I think the love fern was actually kind of cute, but coparenting a dog is a bigger relationship commitment than actually getting married. You can get divorced anytime, but that dog’s gonna live 10-plus years—what was Andie’s plan if she got her way, just leave Ben to care for Krull for the rest of Krull’s yippy life, and then let him suffer unfathomable heartbreak when Krull dies?

(I’ll be right back, I have to go hug my cat, which my then-girlfriend, now-wife acquired after consulting with me because she knew it would one day become our cat.)

Absolute sociopath behavior.

Jenkins: This much is clear: Both of these people are trash. In a way, this makes How to Lose a Guy in 10 Days a near-perfect rom-com: Andie and Ben are truly meant for each other. But in terms of ruling which of our antiheroes takes the crown as the trashest individual, you both make valid points. Andie is noticeably worse for much of the movie—the film is titled after her mishaps, after all—but she has a far less emotionally damaging motive than Ben does, as Claire points out.

What I’m trying to say is that Andie’s numerable actions just about even out with Ben’s one deeply flawed scheme. But ultimately, I have to side with Baumann: Andie was worse. I’ve reached this judgment by concluding that Andie works for a magazine run by an editor who made it pretty clear that they don’t cover politics. If Andie’s intention was to expand the scope of Composure and include more “serious issues,” then that’s admirable—but the movie doesn’t really portray that as the case. Andie simply wants to squeeze into a subject area that her publication has no defined history with. The whole conflict of this movie could’ve been avoided if she freelanced or pursued a journalism job that was more up her alley.

Crazy Rich Asians: Is Nick an Asshole?

Nick (Henry Golding) and Rachel (Constance Wu) have been happily dating for a year, but it’s not until the pair flies to Nick’s native Singapore for a wedding that he reveals the truth about his family: They’re not just rich, they’re everyone-in-Singapore-knows-them, parties-on-custom-container-ships, Rachel’s-friend-plays-chauffeur-just-to-get-a-glimpse-of-Grandma’s-mansion rich. Also unbeknownst to Rachel? That Nick’s entire family expects him to take over the family business in the near future—though he has so far declined in order to stay with Rachel in New York City.

Baumann: Yes

There’s nothing like bolt-from-the-blue-type irrational, emotional love, but having been an old married guy for some time now, I’ve come to understand that the foundation of a functional relationship is trust and honesty. Boring, mundane-sounding stuff to be sure, but without it, any lasting sense of emotional intimacy gets strangled in the cradle.

So let’s say you’re a hot young college professor, dating another hot young college professor, and he’s a nice guy and you’re thinking about settling down. You get a chance to meet his family, which he’s put off because they live overseas, and they’re not particularly close. Understandable. But it’s only en route that you discover that the Nick you think you love is a facade—that he’s the son of dynastic wealth who’s living out a sort of Greenwich Village “Common People” lie.

It’s only after he flies you halfway around the world and leaves you all alone in a new country in the company of a family you don’t know (Awkwafina only barely counts as emotional support), to be judged by prospective in-laws who are determined from the start not only to debase and criticize you, but to send you home in disgrace. Are these the actions of a trustworthy, honest man? No! Rachel should’ve used Nick’s Cathay Pacific platinum miles and booked the first flight back to New York.

McNear: No

OK, hear me out. Dishonesty does not a good relationship bedrock make, I agree. And dishonesty about something that is all but certain to determine the shape (not to mention geography) of Nick’s decades to come? Not great, Bob!

But also: Rachel kind of didn’t seem to mind? When she at long last got the lowdown on the riches from Nick, she reacted as if he’d confessed that his favorite color was actually green, not blue. She admittedly seems surprised once the full, outlandish scale of his family’s wealth comes to light, but she never, for instance, turns to her boyfriend and asks him any number of valid questions ending in “you lying fucking asshole.” Would I like to be in a romantic relationship with someone who spent a year grossly misleading me about their upbringing and future plans? No. But Rachel clearly doesn’t see this as the massive red flag that it is, so who’s to say that Nick didn’t just understand his lady love and what she would and would not consider assholery?

Where Nick does fail is in repeatedly abandoning Rachel to the pack of wolves roaming the Young family abode. Nearly every time he leaves her side, she gets knifed by some auntie or ex-girlfriend or mean-girl bridesmaid or, you know, the would-be mother-in-law from hell. And even though she tells him this is happening, he continues to leave his patient, doe-eyed, utterly unprepared babe in the woods at every turn. The proper response to “The gals broke into my hotel room, wrote ‘YOU GOLD DIGGING BITCH’ in fish blood over my bed, and left the mangled fish corpse on my pillow for good measure”—an actual plot point!—is not “You are so beautiful—and oh, by the way, my batshit sadist mother would like to see you in the other room alone.”

But! Dare I say that Nick seems willing to learn? And if Rachel doesn’t think Nick was an asshole for lying about his family—and she doesn’t—then perhaps he’s not that far off from the dreamboat he apparently was prior to their trip to Singapore.

Jenkins: It is true that trust and honesty are core foundations of a functional relationship, but we are missing a key factor of why Nick lied in the first place: his family, specifically his mother—the most important figure in many a man’s life—had no interest in welcoming Rachel into the family.

There are cultural elements in this story that none of us are qualified to speak to, but the film suggests that Rachel’s Americanness is a big component of her initial rejection. What was Nick supposed to do? Spend his time living in the U.S., completely isolated and devoid of emotional connection, refusing to engage with someone who, by all other accounts, seems to be a perfect match?

Yes, Nick could’ve done a better job of shielding Rachel from his eccentric relatives, but I’d argue that if he had, Rachel wouldn’t have experienced the true nature of Nick’s family—a reality she needed to be aware of if she were to eventually accept Nick’s proposal.

At the end of the day, Rachel, as Claire points out, took less issue with Nick’s (admittedly big) white lie and more with the fact that his mother had put someone she loves in a lose-lose scenario that would result in him either resenting his wife or his family. Nick could’ve handled things smoother, but calling him an asshole feels a biiiiit too harsh for me.

50 First Dates: Was Henry’s Pursuit of Lucy Ethical?

Henry (Adam Sandler) falls for Lucy (Drew Barrymore)—only to learn that a traumatic brain injury has made it so that Lucy’s memory resets to her pre-injury life every morning. This poses a significant hurdle to Henry’s courtship, given that Lucy thinks she’s meeting him anew every day.

McNear: Uh, No

Let’s set aside, for a moment, the great number of extremely serious implications of Henry’s romance with Lucy within the contours of her anterograde amnesia. What I want to talk about is the movie’s ostensibly joyful ending, when a confused Lucy awakens on a sailboat, alone. She spots a video cassette labeled “GOOD MORNING, LUCY,” pops it into the VCR (aw, 2004), and glimpses the years that have apparently passed since the film’s preceding scene. There’s Henry—a man she doesn’t know—and there he is marrying her at their wedding, explaining the diamond ring that sits upon her left hand in present day! Warily, Lucy leaves the cabin and walks to the ship’s deck, where she finds Henry, but he’s not alone: By his side is a young girl. “Would you like to meet your daughter?” Henry asks, and the girl runs into Lucy’s arms.

Excuse me, but what the fuck? Just to zoom in on one teeny, tiny portion of this horror, this suggests that Lucy spent nine months—280 days, give or take—waking up pregnant and having no idea how it happened or who the man with her was. What? What????????????? The VHS trick is cute, but I’m sorry, no amount of Israel Kamakawiwo’ole is going to stifle my screams if I wake up with diastasis recti and zero background intel. WHAT IF SHE WENT INTO LABOR OVERNIGHT? AAAAAAAAAAHHHHHHHHHHHHHH!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

Baumann: Yes

Yeahhh I was hoping you wouldn’t mention the surprise pregnancy body horror thing.

But whatever you’re expecting from a movie when Adam Sandler woos a woman with short-term memory loss, 50 First Dates isn’t it. Henry loves Lucy so much he’s willing to put his own dreams on hold to help her live as full a life as she can, to make her fall in love with him all over again every 24 hours. Rather than just stalling out and doing damage control, Henry helps her keep on living, and through her journals and the videos, Lucy manages to keep up in her own way. Plus there are the little things, like always bringing Lucy’s dad or brother along to let her know she’s safe, that convince me Henry’s heart is in the right place.

This isn’t Phil Connors from Groundhog Day, picking up details about Nancy’s life to convince her she knows him and he can get in her pants. This is basically The Notebook, with a supportive polyamorous walrus friend. It’s sweet.

Jenkins: Oh, God, the surprise pregnancy body horror thing.

Baumann, I admire your willingness to state a defense for such a nightmarish scenario. And not only is your defense admirable, it is accurate. Henry isn’t trying to manipulate Lucy; he’s signing himself up for a difficult life—think about it: would either of you willingly choose to be with someone who forgets who you are Every. Single. Day?—and cares for Lucy with dedication.

Consider the alternative options: Lucy either remains alone due to her condition, or grapples with the potential of sinister men taking advantage of her for god knows how many years. While certainly unconventional, and uncomfortable to a degree, this judge must rule that Henry’s relationship with Lucy is not only ethical, but a virtuous act of love.

Is Journalism One of the Sexiest, Most Romantic Professions?

Romantic comedies have long featured journalists—see: How to Lose a Guy in 10 Days, Runaway Bride, Long Shot, When Harry Met Sally, My Best Friend’s Wedding, Never Been Kissed, Knocked Up, A Christmas Prince, etc. Is the reason Hollywood keeps reimagining the fourth estate’s relationship foibles that the profession itself is inherently—and unusually—romantic?

McNear: You Betcha

Hear me out: Journalism, as it’s presented in the wider cinematic world, does not generally have much to do with journalism—which is to say, the profession that you and I share. With precious few exceptions, journalism in romantic comedies depicts the industry as it was in the mid- to late-20th century at, principally, the big glossy magazines in New York. Deadlines? More of a suggestion, really. Expense accounts? C’mon, do you think Andie Anderson was shelling out for Ben’s Chinese Crested? Salary? Yeah, you’ll be looking down on Central Park from your pied-à-terre. The reporting process? Tell your editor you’ve got a big one; vanish; violate every conceivable industry ethic; return to enormous praise; rinse; repeat. Meanwhile, in some distant fog, Craig Newmark sits down at a computer and begins to type, but let’s not worry about him.

What’s not to fall in love with?

Baumann: No

Claire, you’re making my point for me. Let’s look back on the famous rom-coms that involve a journalist falling in love. Roman Holiday. Sleepless in Seattle. How to Lose a Guy in 10 Days. Runaway Bride. Groundhog Day. In & Out. Never Been Kissed. The Truth About Cats & Dogs. (Bear with me I’m not done.) Knocked Up. 27 Dresses. The Ugly Truth. (Those are three consecutive entries on Katherine Heigl’s IMDb page, for those of you keeping score at home.)

Having a journalist in the story is a useful plot contrivance for a rom-com, because journalists have to travel to new places and meet new people and ask a lot of questions. But journalism is also one of those professions that gives off a particular vibe: curiosity and artistic creativity, but with the security and respectability of a corporate white-collar job. For this reason, you’ll find that the other great overrepresented rom-com profession is architect. (See: How I Met Your Mother, in which an architect falls in love with a journalist.)

You’ll even find journalists in rom-coms when the romantic leads’ professions do not matter in the slightest. There’s a throwaway line in Four Weddings and a Funeral about Carrie working for Vogue. The titular Sally of When Harry Met Sally is a journalist, but so is Jess, Harry’s best friend.

And what do those movies have in common? They were all conceived in a pre–Web 2.0 world, if not a pre-internet world altogether. In a land of glossy photo spreads, with “staff writer” jobs that amounted to one thinkpiece a quarter about how restaurants are to people in the ’80s what the theater was to people in the ’60s. (There is no bigger turn-on for a writer, by the way, than having something you wrote quoted back to you. This is also the premise of Reds.)

But now, after the Great Pivot to Video, those days are gone. We journalists are barely surviving. Look for a contemporary rom-com journalist and you’ll find Fred Flarsky of Long Shot. Fred’s a great guy on paper—he’s smart, funny, confident, kind … maybe he’s not hot, but he’s fairly tall, which I’m told is almost as good. And he gets treated like a joke because he’s a new media reporter in the age of the dismantlement of the news industry by private equity and big tech. Flarskys don’t get secretaries and expense accounts and fancy shoes. They get laid off, do drugs, shout at people, and ejaculate onto their own faces.

Look around. We’re an industry of Flarskys. If we were ever sexy, we aren’t anymore.

Jenkins: Journalists. Spend enough time on Twitter, and you’ll see there is nothing we enjoy more than talking about ourselves. Journalists definitely have some sexy aspects about them: They’re writers, and usually pretty romantic about being so—or romantic on the reporting side of things by “seeking truth” or whatever Tom Hanks says in The Post. There is a reason the plots of 13 Going on 30 and The Devil Wears Prada revolve around magazine editing. And did you see The French Dispatch? A “love letter to journalists,” the IMDb description says. For whatever reason, some people—including prospective romantic partners—seem to consider our professions respectable.

But to Baumann’s point, does that stereotype hold up today? Tell someone you’re a journalist in 2022 and you might get accused of spewing fake news and clickbait. Even on a personal level, you definitely aren’t being handed a company credit card to expense reporting trips to exotic locales unless you work for a select few media outlets. Baumann makes a compelling argument: The Flarskys of the world are vulnerable, and writing doesn’t hold the same prestige as it did in the 20th century.

That said, I believe it is my duty to remind Baumann that work for him today consisted of blogging about fictional rom-com scenarios. Could you make a living doing that in the ’80s?! The romance of journalism may be gone, but the right partner for all of us is one who thinks it is attractive to creatively express ourselves on things we are passionate about. On that level, I have a hard time believing people don’t consider journalists sexy—or maybe that’s just wishful thinking.