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Which Rom-Com Montages Would Make for Good Dates?

Sometimes Patrick Swayze teaches you how to dance. Other times you’re stuck in nightmarish traffic heading to the mall. We broke down 10 classic falling-in-love montages to determine which seem feasible—and which would be complete disasters.

Getty Images/Ringer illustration

As a genre, the romantic comedy rests on a bed of well-worn, time-honored tropes. The meet-cute. The gabby best friend. The split. The dramatic gesture. The happily ever after.

The fall-in-love montage is another of these tropes, wherein our couple goes on a date. Frequently, said date involves touring the local sights; almost always, it ends with a major romantic development—from a first kiss on, uh, down.

But are these montages realistic? That is—would anyone, up to and including extremely ambitious lovebirds, actually plan a date like that? And would our protagonists, you know, enjoy those dates? Or would they spend hours trapped in gridlocked traffic cursing their would-be beloved’s name?

Below, a dissection of 10 such montages from the rom-com genre’s efforts at manufacturing The Best Date Ever.

Totally Feasible

Pretty Woman

The date: Edward (Richard Gere), who had promised to provide Vivian (Julia Roberts) with a new wardrobe and $3,000 in exchange for her company, gives her his credit card in a luxury boutique and instructs the clerk to help her spend a “really offensive” amount of money.

The romantic result: Well, that’s one way to show affection.

Does the geography make sense? Definitely. She sticks to Rodeo Drive.

Total transit time: Negligible. Edward and Vivian’s hotel, the Beverly Wilshire, sits at the base of Rodeo Drive’s famous shopping strip.

Is this a good date? On the one hand, funding a shopping spree is a pretty weird—and frankly not very romantic—thing to do for someone, even if it’s in keeping with the massive power imbalance between high-powered (and moneyed) businessman Edward and sex worker Vivian that forms the premise of this entire movie. On the other hand, the shopping spree comes just after Vivian has her feelings hurt when she gets brushed off by snobby sales clerks at another boutique, and Edward makes a point of demanding that this store treat her with kindness and, moreover, respect. It feels like proof that our guy values her as more than a megawatt smile or a clotheshorse. Also? Vivian has a ball.

13 Going on 30

The date: Jenna (Jennifer Garner) tags along on a series of Matt’s (Mark Ruffalo) photography jobs over the course of a year: a photo shoot for a football team in Central Park, then for a couple on a rooftop overlooking the Empire State Building, and finally for a graduating class on the steps of the New York Public Library’s main branch.

The romantic result: Jenna finds that she likes adulting (and Matt) a lot.

Does the geography make sense? As one-off photo shoots, each is a reasonable destination.

Total transit time: Under an hour.

Is this a good date? Can doing your job—or helping the object of your affection with theirs—be a date? I’d wager that for most people who have had the misfortune of paying bills—that is, adults—the answer is no. But for a starry-eyed tween magically catapulted ahead to adulthood, it takes on the thrill of a middle-school dance (the fun kind from the movies, not the awkward, hormonal horror show from the real world). Matt is chasing his dreams; Jenna is chasing Matt; the snowflakes are falling softly in the big city; everyone wins.

Runaway Bride

The date: After boldly signing up to go where no man has gone before (down the aisle with Julia Roberts’s Maggie), Ike (Richard Gere) spends the couple of days before the nuptials getting cozy with his bride-to-be in her small town—the real-life Berlin, Maryland. He calls Maggie while she’s getting her hair done at the local hair salon; they play cards; he pushes her in a tire swing.

The romantic result: The lovebirds continue to look forward to marital bliss (dun dun dun).

Does the geography make sense? Sure—this small town is indeed small, and some of these scenes take place at chez Maggie.

Total transit time: Negligible.

Is this a good date? Personally, I think a better date might have involved Ike trying to get to know Maggie, instead of turning his troubling, sexism-tinged work assignment—go write about the maneater who keeps leaving men at the altar!—into an essentially spur-of-the-moment decision to tie the knot. It certainly would have made the days to come, when the titular runaway bride, er, runs away once more, easier, if not outright avoidable. But the two do get there in the end, so clearly there was something worthwhile about these moony early days together.

Dirty Dancing

The date: It’s not really a date—it’s just Johnny (Patrick Swayze) teaching Baby (Jennifer Grey) to dance.

The romantic result: A slow-motion side boob graze! An almost-kiss! Nobody puts pheromones in the corner.

Does the geography make sense? Yes. All of these locations are at or around Kellerman’s Mountain House in the Catskills.

Total transit time: Negligible.


You Could Do It

How to Lose a Guy in 10 Days

The date: Ben (Matthew McConaughey) takes Andie (Kate Hudson) to Staten Island, where he grew up (sure!), via the Staten Island Ferry. They travel on his motorcycle to his parents’ home near the Verrazzano-Narrows Bridge, where they proceed to play cards. Then Ben teaches Andie to ride his motorcycle on the Franklin D. Roosevelt Boardwalk before they get ice cream. They get splashed with mud by a passing truck, and return to Ben’s parents’ house to shower before taking the ferry back to Manhattan.

The romantic result: They begin to authentically have feelings for one another and—given they had bickered previously about not yet having slept together—let’s assume that the shower covered some new territory.

Does the geography make sense? It’s a transit-heavy day, and we see Ben turn west out of Staten Island’s St. George Ferry Terminal when his parents’ house is to the east, but it makes basic logistical sense. Says The Ringer’s Dan Devine, who spent his formative years on the island: “I would say that the general framework here—take the ferry to S.I., go see your parents for a little while, quickly get away from your parents, and stop back at the house before going back to your life—rings true.” (One caveat: “The idea that Matthew McConaughey is from Staten Island is one of the more on-its-face inconceivable impossibilities anyone has ever posited. Every Satanic possession/zombie apocalypse/multiverse of madness movie is more plausible than Matthew McConaughey being from Staten Island.”)

Total transit time: The Staten Island Ferry takes about 25 minutes each way. Tack on the motorcycle ride from Andie’s apartment to the terminal in Manhattan (18 minutes), from the ferry terminal to Ben’s parents’ house (which is seemingly in the Shore Acres neighborhood), from there to the boardwalk, and then back to his parents’ house, and that’s another 46 minutes. The journey back to Andie’s comes to a total of 132 minutes (traffic permitting).

Is this a good date? This outing comes about after Andie (on a quest to get Ben to dump her) and Ben (on a quest to get Andie to fall in love with him) go to see a couples counselor. The counselor—secretly Andie’s friend and coworker—proposes that Ben take Andie, who had already attempted to ratchet up the chaos by unilaterally establishing a relationship with Ben’s mom, to visit his family. This is, objectively, a horrendous plan by Ben: At this point in the film, he despises Andie, who’s made a show of becoming progressively more erratic and/or terrifying in an attempt to force Ben’s hand. Taking this person to meet his parents, brother, and young nieces and nephews makes the Bay of Pigs look thoughtful.

But while Ben had literally zero reason to think that this would be anything other than catastrophic, Andie finds—to her surprise—that she likes his family and drops her girlfriend-from-hell act on the spot, allowing the two to have an authentically nice time together. Still, though—while it might have worked out, I’m docking Ben for the sheer idiocy of bringing the person he thought Andie was into his family home (and committing to an all-day, multi-borough sojourn with her, to boot).

In any case, Devine has some tips for Andie’s future visits to in-laws. “If I was trying to plan a daytime date on the island in nice weather, taking the ferry, seeing family, and going out to the boardwalk or somewhere along South Beach would seem like a pretty strong plan,” he says. “There are some outdoorsy types of things to do—hiking in High Rock Park or at the Greenbelt Nature Center—and it’s hard to throw a rock without hitting a pretty good Italian restaurant. But if you’ve already crossed over into ‘meet the family’ territory”—improbably, and foolishly, they had—“this sounds perfectly sweet.”

27 Dresses

The date: Jane (Katherine Heigl) puts on a fashion show for Kevin (James Marsden), trying on each and every one of her 27 bridesmaid dresses and reflecting on the weddings in question.

The romantic result: Not much.

Does the geography make sense? They don’t leave her apartment.

Total transit time: Given the variety of styles and the differing hidden fashion requirements involved—pasties? Shapewear? Hollywood tape?—I think we can assume that executing 27 successive looks took a while.

Is this a good date? Unbeknownst to Jane, Kevin, a reporter, is on assignment at this point, having decided that Jane’s perennial bridesmaid status would make for a juicy story. But while he makes a show of enjoying Jane’s stories, the only thing worse than successively changing into 27 uncomfortable and largely hideous gowns might be having to watch the successive fashion show and feign interest in each new frock. No thanks.

Crazy Rich Asians

The date: Nick (Henry Golding) and Rachel (Constance Wu) land in Singapore. Nick’s friends meet them at the airport and then drive them past the sites—the Singapore Flyer, the Flower Dome, Marina Bay Sands, the Gardens by the Bay—en route to dinner at the Newton Food Centre. Then Nick and Rachel make their way to the Raffles Hotel.

The romantic result: We don’t see them head to bed, but let’s just say they’re reluctant to leave it in the morning—all the more impressive given the jet lag.

Does the geography make sense? In order for this drive-by sightseeing to happen, Nick and Rachel would have had to take a scenic route and do quite a bit of backtracking: We see them driving south past the Singapore Flyer and Flower Dome, then north past Marina Bay Sands—a feasible U-turn, except that immediately afterward they appear to drive east past the Gardens by the Bay, which is south of the first three. To then go to the Newton Food Centre would have them drive past Raffles, though that’s more understandable given the market’s allure.

Total transit time: 72 minutes.

Is this a good date? Presupposing that the pair have a superhuman resistance to jet lag—they flew first class from New York, so maybe those fold-out beds really are all that Big Airline promises—this seems like an excellent introduction to Singapore (and Nick’s friends) for foodie Rachel.

This Just Doesn’t Make Sense

10 Things I Hate About You

The date: Kat (Julia Stiles) and Patrick (Heath Ledger) go paddle boating on Seattle’s Lake Union, then play paintball in Gas Works Park.

The romantic result: They share a romantic, paint-covered kiss.

Does the geography make sense? Sort of. Gas Works Park sits on Lake Union’s north shore, so this would make sense—except that we see them rent the paddle boats from the Center for Wooden Boats, which sits on Lake Union’s south shore. In order to switch to paintball, they would have needed to drop off their boat—which is not exactly the swiftest maritime vessel—and then make their way back to the lake’s opposite end.

Total transit time: 9 minutes (or 53 minutes walking), plus paddling time.

Is this a good date? A scenic locale, good weather, and two novelty activities? Pretty good stuff. But a better date—and who knows, maybe the one taken by bad boy Patrick? Sail (OK, paddle) the boat directly to the paintball site without bothering with all that return-it-to-the-dock, loop-all-the-way-back-around-the-lake nonsense.

Valley Girl

The date: We see a montage of several different dates as Randy (Nicolas Cage) and Julie (Deborah Foreman) fall for each other. On one, they walk down Ventura Boulevard in Sherman Oaks, going past Encino Bowl and the Sherman Theater, among other sights. On another, they look out at the city lights at night—perhaps from the nearby Top of Topanga Overlook. On a third, they engage in that most sacred 1980s teenage ritual: They hang out in the food court at the mall (specifically, the Del Amo Fashion Center). Then he drops her off at her house.

The romantic result: Randy and Julie fall for each other.

Does the geography make sense? Sure. All the locations are reasonable drives from the real Sherman Oaks home that stood in for Julie’s.

Total transit time: While Julie makes several visits to the mall, the real Del Amo Fashion Center is a full hour’s drive south from her Sherman Oaks abode, and that’s if you get lucky with traffic. Surely there are other food courts out there.

Is this a good date? If you can put aside the preposterous mall commute, these make for some classic high school dates—and indeed, they’re enough to set in motion the culture clash of preppy Julie and punk Randy’s different worlds. Unfortunately, it is simply not possible to put aside said preposterous mall commute; it’s hard to imagine Randy not running for the hills when Julie first pitched driving an hour-plus to sup on Orange Julius and Hot Dog on a Stick.

500 Days of Summer

The date: Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel) sleep together for the first time. On his walk to work the next day, Tom stages a celebratory flash mob.

The romantic result: The first part certainly seems to have gone well, but it’s unlikely that commitment-phobe Summer would have enjoyed Tom’s postcoital festivities had she been there to see them.

Does the geography make sense? Nope. Ordinarily, Tom’s walk to the greeting-card company where he works would be a perfectly reasonable jaunt, but he decided to head in the other direction to dance in Grand Park.

Total transit time: His normal 11-minute commute balloons to 41 minutes. Plus dancing.

Is this a good date? Given that Summer ultimately dumps Tom in part for a public display of toxic possessiveness—he picks a fight with a man who attempts to pick up Summer in a bar—it’s hard to imagine her appreciating his extremely public suggestion that the previous evening had turned him into Joe DiMaggio. His ability to manifest cartoon bluebirds out of thin air, though? Tom, you’re wasting your talents.