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That Didn’t Age Well: 20 Rom-Com Movies That Are Problematic Today

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Ignacio Weil

Entertainment - January 17th 2026, 17:00 GMT+1

Cropped All About Steve 2009 — All About Steve (2009)

The whole “quirky destiny” angle plays very differently on a rewatch. *All About Steve* asks you to root for behavior that looks less like romantic persistence and more like boundary-free obsession, with Mary repeatedly ignoring clear signals to back off. The film keeps framing her fixation as cute and fated, which makes the comedy feel uneasy now that audiences are sharper about stalking-coded dynamics. Even when it tries for sweetness, it often turns discomfort into the joke and calls it love anyway. | © Fox 2000 Pictures

Cropped Wedding Crashers 2005 — Wedding Crashers (2005)

A lot of the laughs depend on deception being harmless as long as the guys are charismatic. In *Wedding Crashers*, crashing events, lying about who you are, and pushing past boundaries is framed as a sport – and the movie expects the audience to cheer. Some of its most infamous gags also treat coercion as comedy, which lands with a thud today. The result is a film that’s wildly quotable and still funny in moments, but also built on ideas about consent that feel hard to brush off. | © New Line Cinema

Cropped Hitch 2005 — Hitch (2005)

There’s an undeniable charm to the cast and the glossy New York vibe, but the premise hasn’t gotten kinder with time. *Hitch* treats dating like a system you can game, where the right script and body language can unlock someone’s heart. That “romance as strategy” approach leans on old stereotypes about men as operators and women as puzzles, and it brushes past how manipulative the setup can be. It’s still breezy, but the ethics feel shakier than the movie wants to admit. | © Columbia Pictures

Cropped 13 Going on 30 2004 — 13 Going on 30 (2004)

The fantasy is colorful and comforting, until you think about what the story is actually doing. *13 Going on 30* hinges on a 13-year-old mind navigating a 30-year-old life, which turns romantic beats and adult situations into a weird ethical blur. The movie keeps things light, but the body-swap innocence doesn’t fully protect it from uncomfortable implications around dating, agency, and power. Add the early-2000s makeover logic – status and appearance as the fix for everything – and some scenes feel more dated than dreamy. | © Revolution Studios

Cropped Love Actually 2003 — Love Actually (2003)

It’s a holiday favorite for a reason, but it’s also a bundle of romantic “rules” that don’t glide by anymore. *Love Actually* frames several boundary-pushing gestures as grand romance, including the famous cue-card confession that bulldozes a marriage for the sake of one man’s moment. Other threads lean into uneven power dynamics or casual mean-spirited jokes that stand out on a modern watch. The warmth is real, but so is the sense that the movie often asks women to absorb discomfort so the men can feel brave. | © Working Title Films

Cropped The Wedding Planner 2001 — The Wedding Planner (2001)

The movie wants you swept up in gowns, seating charts, and glittery coincidences, but the central conflict is basically built on crossed lines. In *The Wedding Planner*, Mary is hired to manage a client’s big day and still tumbles into a romance with the groom – played as irresistible fate instead of a professional and ethical disaster. The comedy smooths it over, yet the power dynamics and betrayal angle feel harder to shrug off today. Cute moments survive; the premise is the part that’s aged awkwardly. | © Columbia Pictures

Cropped Bridget Joness Diary 2001 — Bridget Jones’s Diary (2001)

Diary culture, self-deprecation, and “messy but lovable” heroines still have power, yet some jokes land with a sharper edge now than they did in 2001. *Bridget Jones’s Diary* leans hard on body-shaming as a running gag, and it treats workplace harassment as part of the flirtation package rather than a real problem. The love triangle is iconic, but the film often nudges you to accept disrespect as chemistry. It’s comfort-viewing with a side of “wait, we used to laugh at that?” | © Working Title Films

Cropped Shes All That 1999 — She’s All That (1999)

Take away the makeover montage glow and what’s left is a bet that treats a girl’s social value like a prank with a prom budget. *She’s All That* turns “unpopular” into a costume – glasses, paint-spattered overalls, a staircase reveal – then asks you to cheer when she’s deemed worthy after a superficial rebrand. The story also treats humiliation as romance fuel, with consent-adjacent moments played for laughs. It’s a sweet time capsule, but it’s built on a mean little premise. | © Tapestry Films

Cropped Cruel Intentions 1999 — Cruel Intentions (1999)

When a story treats cruelty as sophistication, it’s always going to age in complicated ways. *Cruel Intentions* is deliberately nasty – seduction as sport, manipulation as status – and that’s part of its appeal, but it also plays with consent and emotional harm in ways that can feel grim rather than thrilling now. The film’s “sexy scandal” posture sometimes tips into glamorizing abuse, especially when consequences land unevenly. It’s still stylish and sharp, yet the edge cuts deeper on a modern watch. | © Columbia Pictures

Cropped Never Been Kissed 1999 — Never Been Kissed (1999)

There’s something queasy about a rom-com that depends on an adult pretending to be a teenager and then flirting inside that world. *Never Been Kissed* tries to sell the setup as harmless undercover chaos, but it blurs boundaries in ways modern audiences are far less willing to excuse. The teacher-student tension is especially uncomfortable, not least because the film treats it like romantic destiny rather than a loud red flag. It’s earnest and nostalgic, but the concept carries baggage the script can’t outrun. | © Fox 2000 Pictures

Cropped Addicted to Love 1997 — Addicted to Love (1997)

Revenge is the engine, romance is the garnish, and that mix reads harsher now than it probably did in the late ’90s. *Addicted to Love* treats stalking-adjacent behavior as quirky payback, with characters surveilling exes, breaking into spaces, and escalating obsession under the guise of being “hurt.” The film wants you to enjoy the chaos as catharsis, but it also normalizes a level of fixation that feels less screwball and more unsettling today. Even when the story winks at how messy everyone is, it keeps turning boundary-crossing into entertainment, then hopes the chemistry makes it all feel charming. | © Warner Bros.

Cropped Clueless 1995 — Clueless (1995)

A lot of teen comedies from the era feel rougher with time, but this one’s complicated because it’s also unusually self-aware. *Clueless* is still sharp and funny, yet some of its “dating logic” is very ’90s: casual homophobia pops up, and the famous step-sibling romance is an idea many viewers now side-eye even if the film treats it as harmless. The makeover culture and popularity economics are part of the satire, but the movie also helped cement them as aspirational for a generation of viewers. It remains a classic, just one that shows how quickly social norms around language and relationships can shift. | © Paramount Pictures

Cropped While You Were Sleeping 1995 — While You Were Sleeping (1995)

The premise is cozy and the wintery vibe still works, yet the setup asks you to accept a lie that grows way past “awkward misunderstanding.” In *While You Were Sleeping*, Lucy is pulled into a family’s life while they believe she’s engaged to a man she barely knows, and she goes along with it long enough that it starts feeling ethically murky. The movie plays the situation as sweet wish-fulfillment – lonely woman finally seen – while glossing over how strange it is to build intimacy on mistaken identity. It’s a warm rom-com, but it also depends on deception being forgiven because everyone’s nice and the ending is heartfelt. | © Hollywood Pictures

Cropped Sleepless in Seattle 1993 — Sleepless in Seattle (1993)

There’s a dreamy softness to the radio voices and city skylines, but the romantic ideal here is basically long-distance obsession. *Sleepless in Seattle* hinges on a woman getting so invested in a stranger that she upends her life, and the story frames that fixation as fate rather than a warning sign. It’s not the darkest version of rom-com weirdness – it's gentle and sentimental – but it still treats emotional projection as proof of love. Modern audiences tend to want more mutuality and less destiny-by-audio-clip, which makes parts of the setup feel dated even when the charm holds. | © TriStar Pictures

Cropped Chances Are 1989 — Chances Are (1989)

The hook is bold, but it also drags romance into territory that gets uncomfortable fast. *Chances Are* involves reincarnation, age gaps, and a relationship that’s tangled up in family history in a way that can feel queasy rather than magical. The film wants you to buy the idea that true love can loop through lifetimes, yet it creates a dynamic where consent and appropriate boundaries are inherently messy because of who knows what... and when. It’s a fascinating late-’80s swing, just one that now plays like a thought experiment the genre has mostly learned to avoid. | © Columbia Pictures

Cropped Big 1988 — Big (1988)

The wish-fulfillment is undeniable, but the romance is where the movie starts to squirm under a modern lens. In *Big*, a child wakes up in an adult body and ends up in a sexual relationship with a grown woman who believes she’s dating a man – yet the film plays it as sweet, funny, and ultimately harmless. Rewatching now, it’s hard not to focus on the consent problem baked into the premise, because the emotional reality never matches the physical situation. The movie still has a lot of heart, but the storyline asks viewers to laugh past something that would be deeply alarming outside a fantasy comedy. | © 20th Century Fox

Cropped The Breakfast Club 1985 — The Breakfast Club (1985)

It’s still one of the most quoted teen movies ever, but it also carries the casual cruelty of its era like a badge. *The Breakfast Club* treats harassment and boundary-pushing as “boys being boys,” and it sometimes frames violation as a stepping stone to sincerity. The film’s gender politics can feel especially dated in scenes where a character’s pain is used for laughs or as social leverage, and the empathy doesn’t always extend evenly to everyone in the room. Even so, its emotional honesty about loneliness and identity still hits – just alongside moments that make you wince because the movie doesn’t realize they’re problems. | © Universal Pictures

Cropped Blame It on Rio 1984 — Blame It on Rio (1984)

The vibe is sun-drenched and supposedly sexy, yet the story’s idea of “forbidden romance” is soaked in power imbalance. In *Blame It on Rio*, an older man’s relationship with a much younger woman is treated as a cheeky escapade, with the comedy coming from lies, sneaking around, and everyone acting like it’s just awkward timing. Watching now, the age gap and the way the film leans into titillation make it feel less like naughty farce and more like a portrait of adults making selfish choices at a teenager’s expense. The movie keeps insisting it’s playful; the modern reaction is often closer to discomfort. | © 20th Century Fox

Cropped Sixteen Candles 1984 — Sixteen Candles (1984)

A lot of people remember the jokes and the dance, but the parts that linger now are the ones that shouldn’t have been jokes in the first place. *Sixteen Candles* includes racist caricature played for laughs, plus a storyline that treats sexual assault and intoxication as comic setup rather than a serious violation. The film also normalizes the idea that a girl’s humiliation is a fair trade for a guy’s big romantic moment, which can make the whole “birthday blues” plot feel meaner than nostalgic. It’s influential teen comedy history, but it’s also a clear example of how mainstream movies once waved off harm as harmless fun. | © Universal Pictures

Cropped Endless Love 1981 — Endless Love (1981)

What the film sells as all-consuming passion can read, today, like obsession with a glossy soundtrack. *Endless Love* romanticizes intensity – jealousy, fixation, escalation – without much interest in the emotional damage those behaviors cause. The central relationship is framed as fate, even as it veers into controlling territory and treats boundary-breaking as proof of devotion. In an era more attuned to toxic dynamics, the movie’s “love above everything” message can feel reckless, because it blurs the line between romance and danger until the consequences hit. | © Universal Pictures

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Rom-coms are supposed to be comfort food – easy chemistry, big gestures, happy endings. Rewatch enough favorites, though, and the sweetness can curdle: jokes hit differently, “romance” starts to look like pressure, and certain story beats feel oddly mean in hindsight.

It’s not about canceling an entire genre; it’s about noticing what time has made obvious. Some tropes now stand out like neon – casual sexism, persistence treated as destiny, punchlines built on queer stereotypes, and power dynamics the script waves away with a wink.

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Rom-coms are supposed to be comfort food – easy chemistry, big gestures, happy endings. Rewatch enough favorites, though, and the sweetness can curdle: jokes hit differently, “romance” starts to look like pressure, and certain story beats feel oddly mean in hindsight.

It’s not about canceling an entire genre; it’s about noticing what time has made obvious. Some tropes now stand out like neon – casual sexism, persistence treated as destiny, punchlines built on queer stereotypes, and power dynamics the script waves away with a wink.