Uptown Girl

""On the right side of the tracks she was born and raised. In a great big ol' house full of butlers and maids.""

- Stevie Wonder

You know the story. True love overcomes all obstacles, including little things like money and caste in the tale of the peasant falling in love with the princess, or the poor Unlucky Everydude falling for the daughter of the wealthy family. This can start in a few ways. Maybe it was Love At First Sight. Maybe she's sneaking out for a night on the town and they run into each other. Maybe they've been friends their whole lives, and the difference in wealth never really mattered.

In any case, this is usually played out in one of three ways:
 * The poor guy and rich girl mutually fall in love, and neither one cares about their differences in wealth. People around them, however, do, and conspire to interfere with True Love.
 * The poor guy falls for the rich girl, even though he knows that she's out of his league. Undaunted, our hero engages in some Zany Scheme to get her to notice him or be impressed by him. This usually ends with the girl revealing that she doesn't care if he's rich or poor, and that she loves him for who he is.
 * The poor guy and the rich girl fall for one another, but he doesn't know she's rich at first. When he finds out, he's either intimidated by her wealth once he finds out, or else doesn't think he's good enough for her. As before, she doesn't care about such things, and has to convince him that he's the one she wants.

When the rich girl wants nothing to do with the poor guy, but slowly warms up to him, it's a different Trope entirely.

Note that the roles aren't locked into the rich one in the relationship always being the girl, while the guy is the Unlucky Everydude. It is entirely possible for the roles to be reversed, or for both persons to be the same gender.

A relationship variant of the Odd Couple and quite often a subtrope of Nobody Thinks It Will Work. Also often leads to cases of I Can't Believe a Guy Like You Would Notice Me, either with severe case of insecurity (like the third type above), or simply the poor guy being constantly feeling lucky and appreciative that someone so rich could fall for him. Compare with All Girls Want Bad Boys, which often follows the same socioeconomic groups. Can overlap with Single Woman Seeks Good Man as it is the guy's personality that wins her heart (as is the case mentioned above).

Not to be confused with the Brittany Murphy film Uptown Girls which doesn't use this trope. Not to be confused with City Mouse either.

This is transitioning into Dead Horse Trope territory, since interclass marriage is no longer shocking, and the expectation that men should be the breadwinner in the family is much weaker today than it used to be. On the other hand, it may become an Undead Horse Trope with the emergence of culture wars and new waves of social stratification in recent years.

Anime and Manga

 * Hayate the Combat Butler. A little one-sided, at least at the start, as Nagi (the rich girl) has become infatuated with the extremely-poor Hayate after he saves her from kidnappers. She saves him from his (parents') debt, and he ends up serving her as a Battle Butler to pay her back. For her, it seems to be mostly just an excuse to keep him around.
 * Hana Yori Dango (although it's a bit more complicated than that, obviously).
 * To elaborate: Tsukasa Domiyouji is a rich bully who falls in love with the poor-as-dirt Tsukushi Makino. Depending on where you are in the series, she either loves his rich friend Rui Hanazawa, and it's difficult to tell what goes on in his head. Later in the series it revolves around the problems associated with Tsukasa and Tsukushi being together since he's the heir to a super-rich corporation and she's just a Japanese commoner.
 * The Beta Couple of Soujiro and Yuuki also counts, still with the guy as the Uptown Girl and the girl as the pauper.
 * Lina from Heroman comes from a rich-looking family while Joey looks really poor, although this fact isn't brought up at all, although it was hinted at by Lina's dad.
 * Mobile Suit Gundam 00 has Saji Crossroad, a poor Unlucky Everydude, fall for Louise Halevy, a Spoiled Sweet Tsundere, whose family is implied to be extremely wealthy and influential. The series seems to subvert the expectation that Louise's family would be hostile to Saji, as Louise's mother quickly takes to him, especially after hearing that he's an orphan, and basically treats him like a second child (which actually makes Louise jealous, a reaction played for comedy). Unfortunately, the series has a large dose of Break the Cutie for both of them.
 * In Victorian Romance Emma is an example where the gender is switched. Emma, an orphan maid, is pursued by, and falls in mutual love with, William Jones, a wealthy member of the upper-class gentry. In this case it's a matter of the third version of this trope, with Emma thinking that her lack of refinement and rank will only hurt William's station and cause trouble for him if they were to marry. The Parental Marriage Veto doesn't help matters.
 * Nogizaka Haruka no Himitsu centers around this. The titular Nogizaka Haruka is the daughter of a ludicrous wealthy and powerful family, and the lower-middle-class Ayase Yuuto initially winds up as her confidant when he accidentally discovers her deep, dark secret... that she's an anime & manga otaku! As they spend time together, however, a relationship blooms - initially a type-1, but as Yuuto realizes just HOW wealthy her family is, and what kind of powerful people she usually rubs elbows with (not to mention what kind of men are actively pursuing marriage with her), he slips into a type-3 as he starts to feel 'unworthy' of her. Her father agrees, but who knows? Maybe there's a way for him to gain their respect...
 * From Umineko no Naku Koro ni, George, a member of the obscenely wealthy Ushiromiya family falling in love with Shannon, one of the servants at the main house.
 * Tsubasa Reservoir Chronicle: Sakura (princess) and Syaoran (middle class).
 * Howl's Moving Castle: Sophie (middle-class) and Howl (famous wizard).
 * In Shinshi Doumei Cross, Haine is poor and Shizumasa is rich. Slightly inverted in that Haine is not poor in any real sense; she's just significantly less wealthy than Shizumasa. Still, it plays just as the trope is described.
 * The Secret Agreement contains examples of both wealth and class differences, with Iori being the only male heir to an increasingly poor but noble family and set to marry into a wealthier but less respectable family for their mutual benefit. Meanwhile his actual lover is a former Street Urchin and fears if Iori marries he'll never see Iori again because the family won't need him to quietly sell off their possessions anymore (the only reason their friendship was tolerated in the first place).
 * Zigzagged in Maiden Rose. Taki is second-in-line to the throne in his own country. When Taki and Klaus first meet Klaus is of the nobility. Eventually Klaus' family lose that status because the monarchy is dissolved when the country falls to the Western Alliance, placing him in the wealthy middle class. Later, when Klaus becomes Taki's knight, he has to renounce his country, his name and status and becomes the lowest of the low in Taki's country. Their romance has been developing through all of this, but really comes into force after Klaus has lost his upper-class status.
 * Subverted in Hana Wa Junai Ni Junjiru, where Tsubaki (presumably lower class himself) is being trained to be a high-class prostitute serving only the nobility and Daniel is a gardener at the manor. Daniel works to be knighted just so he can be with Tsubaki, but his fixation on class causes even more tension because Tsubaki doesn't want to be associated with the noblility's prostitute system and would rather Daniel had run away with him when they were kids.
 * In Hanakage No Kioku, Laurent is a butler who has been with Arthur's family since childhood, and initially rejects Arthur because of his status. Arthur's friend from school also tries to romance Laurent.
 * "Rich sheik abducts Japanese everyman" is a stock plot in Boys Love manga/light novels, with Eternal Love, Kyokutou No Hanamuko, Sabaku No Oujisama, Ouji To Kotori and Sarou No Ryoshuu being but a few examples.
 * Subverted in Flaming Ieraishan where a reporter falls in love with the heir to a viscount, who ends up running away and becoming a prostitute when his family is ruined. It then turns out the viscount was impotent and Saki's actually the son of a prostitute who he sheltered in order to appear to have an heir.
 * Mr Kayashimas Graceful Life features an emotionally stunted Upper Class Twit whose only real interest in life is his relationship with his gardener.
 * Due to their supernatural connection, after Mikhail forces Kiri to become his servant, they begin a physical relationship which eventually evolves into a romantic one in Wild Rose.
 * In Tsukigasa, Azuma's family is loaded, whereas Kuroe is of a slightly more modest background.
 * Nadeshiko Amamiya and Fujitaka Kinomoto in Cardcaptor Sakura. Resulted in Nadeshiko being disowned by her wealthy family; she doesn't mind that much as Fujitaka was no Gold Digger, and she works as a model while he continues teaching and they live in a tiny but cozy apartment with their children.
 * Claudine de Montesse found himself as an Uptown Boy in regards to his first love Maura, a Country Mouse who worked as a maid in his family's Big Fancy House. Made even more complicated by Claudine being transsexual.

Comic Books

 * Peter Parker and Liz Allan are played this way in The Spectacular Spider-Man, though Peter eventually becomes something of a cool nerd.
 * Legion of Super-Heroes. Tinya Wazzo is (Phantom Girl) is the daughter of a rich, high-society family. Jo Nah (Ultra Boy) is a former gang member who lived on the streets.
 * Archie and Veronica from Archie comics. (But not Archie and Betty, because Betty is a Girl Next Door).
 * Inverted in Nikolai Dante - Galya is a poor peasant girl, while Viktor is a member of the aristocratic Romanov family. Dmitri doesn't take it well.
 * In Maus, Vladimir Speigleman was working class, albeit very resourceful. He ended up marrying Anya, the daughter of a millionaire.

Fanfic

 * Almost any fanfic pairing the aristocratic Inspector Lynley and his working-class partner Sergeant Havers will inevitably have to deal in some fashion with their wide social disparity.
 * Xiaolin Showdown: Raimundo and Kimiko.

Fairy Tales

 * The tale of "Aladdin": it's firmly in the Zany Scheme category, with Aladdin going to enormous lengths to get the rich princess.
 * The Disney version is a mixture of the second and third, "insecure about his poverty," variety, as well as having the Princess desire to leave the palace and live on her own.
 * There are quite a few fairy tales of the poor nobody youngest son winning the hand of the princess. Sometimes it lasts, sometimes it ends badly. In general, if it's gender-reversed (as in "The Goose Girl") the girl is a really a princess herself, who has been driven to a life of poverty, usually by a wicked stepmother.
 * "Cinderella" and all its clones.
 * "The Valiant Little Tailor".
 * From The Brothers Grimm: "Die Kluge Bauerntochter" ("The Peasant's Wise Daughter").

Film - Animation

 * Disney's Tangled fits the trope, with Rapunzel and bandit Flynn Rider.
 * Though in this case their differences in wealth and status are never addressed.
 * Disney's Sleeping Beauty is set up to be this, but it turns out that the beautiful peasant girl Philip sees in the forest is the princess he's betrothed to.
 * Lady and the Tramp: She's the pedigreed pet of a well-to-do family, he's a streetwise stray mutt.
 * The Aristocats has pampered pet cat Duchess and laid-back alley cat Thomas O'Malley.
 * Antz has a lowly worker ant pretending to be a soldier to impress a princess.
 * A Bugs Life features a similar plot.
 * The Princess and the Frog has rich (but cut off) Naveen and poor Tiana. Interestingly enough, the usual story is Inverted by the fact that, in the end, the prince gives up his claim to the throne to live a commoner's life with his new wife.
 * Gaston tries to invoke a gender-reversed version of this in Disney's Beauty and the Beast by wooing Belle, "the inventor's daughter". She doesn't go with it. Played with in the case of Belle and the Beast. While the Beast is actually a prince and, as stated before, Belle is a poor girl, the Beast also starts out pretty much as an animal with Belle being much more civilized and graceful than him.
 * In Disney's Tarzan, Jane is a London girl. Tarzan literally lives with gorillas. She ends up loving life in the jungle far more than life in the city.
 * Cinderella (a servant girl-turned princess) and Prince Charming (guess).
 * Aladdin (a "street rat") and Princess Jasmine (the daughter of the local Sultan).
 * The Hunchback of Notre Dame has the wealthy knight Phoebus and the poor Gypsy Esmeralda.
 * "An outlaw for an in-law!"
 * Atlantis the Lost Empire has Milo Thatch, a definitely lower-middle class academic and "Kida" Kidagakash, a beautiful Atlantean princess. However, given that Atlantis is in something like a low-level After the End situation it's anyone's guess who's the wealthy one.
 * The Emperors New School has Kuzco, a cocky young South American emperor, and Malina, a beautiful peasant girl.
 * The Lion King, Simba's Pride, has Simba's daughter Kiara, a lioness princess, and Kovu, a renegade lion.
 * The Nightmare Before Christmas has Pumpkin King Jack Skellington and Mad Scientist's Beautiful Daughter Sally.
 * Shrek and Fiona. He's an ogre, she's a princess.

Film - Live Action
"William: Where will we live? In my hovel, with the pigs inside during the winter so they won't freeze? Jocelyn: [crying] Yes, William...with the pigs."
 * Pretty in Pink is another gender-reversed example.
 * Claire and Bender from The Breakfast Club play it straight.
 * In Some Kind of Wonderful, the poor guy pursues the rich girl,.
 * The first three Pirates of the Caribbean films have Elizabeth Swann (the Governor's daughter) and Will Turner (blacksmith's apprentice).
 * Titanic's Rose DeWitt Bukater hated the uptown life so much that she contemplated suicide though it took a few scenes before she sums up the nerve to leave Cal.
 * Crazy/Beautiful
 * Wild at Heart has Lula Fortune, with her lover Sailor Ripley being from a much poorer background and recently released from jail as the film begins.
 * Say Anything. The image of Lloyd Dobbler standing across the street from Diane Court's house, holding a boom-box over his head has pretty much become a romantic icon.
 * Gender-reversed in Drag Me to Hell. Christine is clearly from humbler roots than wealthy Clay and the whole plot is caused in part because she wants a promotion to measure up to his family.
 * In The Notebook Allie's parents think that Noah isn't good enough for her because he works at the lumber mill.
 * In Daddy Long-Legs, the orphan Jerusha "Judy" Abbott ends up with her rich benefactor.
 * Pretty Woman has a rich man and a sex worker fall in love.
 * In A Knight's Tale, William tries to get his Blue Blooded love interest to face the realities of life with him, a destitute fugitive from the law.


 * In The King and the Clown the King's fixation with a male street clown is a major point of contention in the court and used to help justify their coup. The King's Hot Consort Nok-su is implied to also have caused friction for being lower class, but Nok-su is better at court intrigue than Gong-gil is.
 * In ATL, poor aspiring artist Rashad meets mysterious girl New-New at a skating rink. He doesn't know much about her background, but eventually finds out that New-New is filthy rich and her real name is Erin.
 * In Nanny Mc Phee Returns, we see that the mother was from a wealthy family and ended up being Happily Married to a farmer. When her brother describes her as having made an "unfortunate marriage", her son is not pleased.
 * In the Iron Man series, while Pepper Potts is not exactly poor, she is nowhere near the social circles her multi-millionaire playboy boss Tony Stark is in. By the end of the second movie, they're going steady.
 * In Jumping the Broom, while Jason is not poor, he came from a poor background and made his money by himself. His fiance Sabrina comes from old money, however, and this is the basis of the plot.
 * The Lover (or L'Amant) is a 1992 French film based on the novel of the same name by Marguerite Duras. Set in French Indo-China in 1929, it depicts the illicit affair between a fifteen-year old French girl from an impoverished family and her wealthy Chinese lover—as a result the trope applies to both parties due to the racial/social divide.
 * Love Story is another gender-swapped example.

Literature
""From what I have seen of the lady, she seems, indeed, to be on a very different level to Your Majesty," said Holmes, coldly."
 * Pride and Prejudice. Lady Catherine throws a hissy fit over someone as (relatively) low-class as Elizabeth marrying Mr. Darcy. Elizabeth wins this by exposing Lady Catherine not as a snob, but an idiot: "He is a gentleman. I am the daughter of a gentleman. Therefore, I am his equal." Which is absolutely true. Mr. Bennett is a landowner, an esquire, just like Darcy (he just owns less, or less profitable land); they are of exactly the same social class. That some modern readers fail to understand that 'class' in the 1790s was defined by where your money came from, not how much you made, is understandable, but for Lady Catherine to forget it (or at least expect Elizabeth not to realize it) makes her a complete ass as well as a bully.
 * Lady Catherine's opinion on Lizzy's class was not, at the time, uncommon. While technically Darcy and Mr Bennett are of the same social class, the former is descended from a very old and wealthy landowning family on one said and straight-out nobility on the other. Mr Bennett is a landowner, if a rather small one; but his and his wife's relatives are merchants and lawyers. To Lady Catherine, a peer both by birth and marriage, the idea of having Darcy bring a niece of merchants and lawyers into her family would be utterly repugnant. It helps that she already has plans for him to marry a noblewoman and keep all the wealth in the family.
 * This is a subplot in the Robert Westall book Fathom Five.
 * Yukio Mishima's The Sound of Waves has a poor boy falling in love with a rich girl, and her father doesn't approve and there's Malicious Gossip and all that. The boy eventually gains the father's approval by going out on one of his fishing boats and saving it from being wrecked in a storm.
 * Gatsby and Daisy in The Great Gatsby.
 * Captain Sam Vimes and Lady Sybil Ramkin (subsequently Sir Samuel and Lady Sybil Vimes) in Discworld, although older than the usual examples of the trope. The resultant class dynamics lead to Vimes being seen as "a jumped-up copper to the nobs, and a nob to the rest".
 * Hinted at/set up for next book in Scott Westerfeld's Leviathan - Alek (rich) and Deryn (poor).
 * Unfortunately, it's a little more complicated than that. Alek is a prince, and Deryn is "as common as barking dirt." And he's already told Deryn (unaware that she's in love with him) that if he ever loved a commoner, he'd immediately put as much distance between them as possible. He grew up feeling like he never should have been born due to the... difficulties of his parents' interclass marriage, and he refuses to do that to his own children.
 * Tennyson's The Beggar Maid: "Cophetua sware a royal oath: 'This beggar maid shall be my queen'" (This was itself based on an old ballad, The King and the Beggar-maiden.)
 * The same author's The Lord of Burleigh.
 * Little Women: One of the March sisters is expected to marry their rich neighbor Laurie. Eventually Amy does.
 * Twilight. Bella's strictly working class. The Cullens are wealthy (its easy to make money if you're immortal and a smart investor).
 * Debateable. Bella is probably middle class (such as being given a second hand truck on arrival) but in comparison to the Cullens who are ridiculously and impossibly rich she is poor.
 * The Sherlock Holmes story A Scandal in Bohemia has the "rich guy, common girl" romance with the Prince of Bohemia and Miss Irene Adler. Used to show how superior the resourceful and clever Miss Adler is to her 'superior':


 * This is the major source of dramatic conflict in Lady Chatterley's Lover, where the well-bred lady of the gentry takes up with the gardener. Played with and doubled in that she was a Rags to Riches story herself, having been working-class before marrying her rich husband Lord Chatterley.
 * In The Princess Bride. Buttercup gets made princess of a tiny area in order that Prince Humperdinck can marry her. This also puts her socially above Westley who used work as her farmhand before becoming a pirate.
 * In Maurice, after a failed platonic romance with Clive, Maurice has sex with the under-gamekeeper at Clive's estate. Their class difference even more than their homosexuality is what nearly stops them from pursuing a real relationship.
 * Sarah Biddle, the orphaned housekeeper and David Braddock, the wealthy Philadelphia businessman, during the late 1800s in Stephanie Grace Whitson's Sarah's Patchwork, the first book in her Keepsake Legacies series.
 * In The Premature Burial by Edgar Allan Poe, there is a story about a young French woman named Victorine who came from a wealthy family and had a relationship with a poor journalist named Julienne.
 * In Harry Potter, Harry isn't obscenely upper class, but he's very well-off and, by his sixth year, is pretty popular. He ends up dating and later marrying Ginny Weasley, who is from a poor "blood traitor" family.
 * Simone Elkeles' Perfect Chemistry is this, with Brittany Ellis (rich, privileged white girl) and Alejandro "Alex" Fuentes (poverty-class, Latino, in a gang). The town they live in heavily segregates between the north side (upper class) and the south side (lower class).
 * One Day reverses the genders with wealthy upper-class Dexter and the more modestly brought-up Emma in a Will They or Won't They? situation.
 * Sweet Valley High had a few examples of this, such as one book where a visiting European prince falls for blue-collar Dana. There's also the spin-off Elizabeth series where Elizabeth goes to London and falls in love with an aristocrat while working as a servant at his manor house.
 * Working-class Adrian Mole and his aristocratic first wife Jo Jo.
 * In Spy High, wealthy Ben is initially drawn to the equally privileged Lori; but his true love turns out to be wrong-side-of-the-tracks Cally.
 * The Noughts and Crosses series is based on this, though the books have their own class system where the dark-skinned Crosses dominate the fair-skinned Noughts.
 * Ship Breaker seems to be setting this up between light crew ship breaker, Nailer, and Nita, whose father is one of the richest men in the world. Nothing's happened yet, but there's been lots of Ship Tease and one kiss so we'll see...
 * Although most adaptations gloss over or ignore the fact, the aristocratic Raoul pursuing a marriage with opera singer Christine in The Phantom of the Opera is rather unorthodox and a source of major contention between Raoul and his older brother Philippe. The public, unaware that there's a criminally insane Stalker with a Crush in the mix, assume the mystery surrounding the young couple's fate has something to do with the brothers' falling out.
 * PG Wodehouse liked to parody this trope. The in-universe romance novels by "Rosie M. Banks" were entirely centered around romances of this kind, and brimming with Stylistic Suck.

Live Action TV
"H: Can it be possibly true? Surely love has never crossed such boundaries of class? (clutches Amy's hand) A: But what about you and Mum? H: Well, yes I grant thee when I first met her I was the farmer's son and she was just the lass who ate the dung, but that was an exception. A: And Aunty Dot and Uncle Ted. H: Yes, yes alright, he was a pig poker and she was the Duchess of Argyle, but- A: And Aunty Ruth and Uncle Isaiah, she was a milkmaid and he was- H: The Pope! Yes, yes, all right."
 * Cheers. The relationship between Woody the bartender and the millionaire's daughter Kelly Gaines.
 * Sam and Diane were the series's first example, despite the fact that Diane only acts like an uptown girl. Rebecca, both as the corporate Iron Lady, and then later as the simpering Yuppie Butt Monkey, managed to subvert this trope.
 * Dwayne Wayne and Whitley Gilbert in A Different World definitely fits here, Dwayne being the college nerd Everyman and Whitley the upper crust snob. Dwayne didn't start pursuing her until Season 3, but from there it was pretty much your average sitcom relationship, starting with Type 2 and progressing to Type 1 and eventually marriage through a course of break-ups and 'desperately in love with you' revelations.
 * Dharma and Greg has a lot of similarity to the poor-guy rich-girl story type, but is actually an aversion in that, though Dharma's parents live the hippy lifestyle, they aren't doing that badly for themselves financially.
 * Malcolm in the Middle. Hal comes from a very rich family than openly hate Lois.
 * Desmond and Penny, on Lost. Also Jin and Sun.
 * Ryan and Marissa. This is the primary storyline for the first half of The OC.
 * There's Double Secret Subversion in Dirty Sexy Money. Ultra-rich Jeremey Darling meets a beautiful woman named Sofia while temporarily working as a valet in one of his family's business. He falls in love with her, then pretends to be a starving artist to prove to himself he can win her over without disclosing his real identity as (essentially) an Upper Class Twit. The story doubles up on this trope because Jeremy was the poor boy going after the rich girl, when it was the girl who was the poor (well, okay, comparatively poorer) one all along.
 * Episode 2 of the third season of Ashes to Ashes specifically references this trope via a Non Sequitur Scene which doubles as a Crowning Moment of Funny. Rich girl Alex and downtown boy Gene replace Billy Joel and Christie Brinkley in the music video for "Uptown Girl" itself (with Ray, Chris, and Background Cop #3 filling in as backup singers).
 * Not to mention Gene's favourite nickname for Alex: "Bolls/Bolly/Bollinger Knickers". Bollinger is a type of champagne.
 * Also emphasised in 3.2 with the dating agency forms, when Alex's favourite meal is "roast foie gras with gooseberry, braised konbu and crab biscuit" which she had whilst on holiday in northern France, whereas Gene's is steak and chips.
 * In an episode of The Suite Life of Zack and Cody, Maddie falls for a rich guy and attempts to look and act rich so he will like her.
 * Gender flipped with Gwen and Arthur in the BBC show Merlin.
 * Not to mention he is royalty and she is a servant.
 * Mallory and Nick from Family Ties.
 * Virtually all Latin American soap operas are built around the rich guy, poor girl dynamic.
 * Jeeves and Wooster plays around with the trope. One of Bertie's friends wants to marry a waitress. To convince his uncle that it's a good idea, he makes him read romance novels where chambermaids end up marrying their masters.
 * From the Blackadder episode "Amy and Amiability":


 * Hyde and Jackie from That '70s Show (while they were a couple). Jackie is a rich girl and cheerleader, Hyde is a poor delinquent with a messed up family who lives with Eric's family because he has nowhere else to go. Initially Hyde stated their differences in social status as a reason they shouldn't go out, as they had nothing in common.
 * In Downton Abbey, this seems to be developing between Lady Sybil, the earl's youngest daughter, and Branson, the family's Irish socialist chauffeur
 * Super Sentai has some examples:
 * Yukito and Emiri in Bakuryuu Sentai Abaranger
 * Engine Sentai Go-onger hinted at a romance between impoverished Sousuke and wealthy Defrosting Ice Queen Miu. Would also apply to the popular fan-pairing of Saki with Miu's brother Hiroto.
 * Hikaru and Urara in Mahou Sentai Magiranger would count, since Urara is a middle-class human girl whereas Hikaru is the future ruler of Magitopia.
 * Although not canon, a lot of Samurai Sentai Shinkenger fans were rooting for the pairing of samurai princess Kaoru with poor sushi seller Genta.
 * Robin and Kate in series three of Robin Hood
 * Working-class Rodney and well-heeled Cassandra in Only Fools and Horses. Before meeting Cassandra, Rodney also dated earl's daughter Lady Victoria.

Music

 * The Trope Namer is Billy Joel's "Uptown Girl", about a low-class street kid who falls for, and pursues the affections of, a rich "uptown girl".
 * Uptight (Everything Is Alright)  by Stevie Wonder.
 * The song "We Both Go Down Together" by The Decemberists is about a wealthy young man who falls in love with a poor girl. It doesn't end well for either of them.
 * Paul Simon's "Diamonds on the soles of her shoes" from Graceland is explicitly about this trope.
 * "Dawn" by the Four Seasons. The same group also did a gender-swapped version of the trope, "Rag Doll", in which the male singer is in love with a poor girl.
 * "West End Girls" by the Pet Shop Boys ... probably.
 * From the Jay And The Americans song "Only in America": "Only in America / Would a classy girl like you fall for a poor boy like me!"
 * The song "Down In The Boondocks" is about a poor boy in love with a rich girl.
 * Spanish band Amaral made a cruel subversion of this trope in their latest album, where the girl gets into drugs and heavy drinking and esentially wastes her life intoxicated.

Religion and Mythology

 * The Old Testament's Joseph (whose story is told in Genesis, chapters 38 through 41). As a priest's daughter Asenath was certainly socially miles above a former slave...
 * Averted Trope: Then again, that former slave was Prime Minister of Egypt, as well as being the son of a very wealthy foreigner who just happened to have envious half-brothers.

Newspaper Comics

 * Blondie. The original strip was about the well-to-do Dagwood marrying the distinctly lower class Blondie against his parent's wishes. He was cut off and had to get a real job; the strip gradually morphed into the Dom Com it has been for most of its run.

Theater

 * The opera Arabella by Richard Strauss. Impoverished Patrician Arabella falls for landowner Mandryka, solving her family's money worries.
 * John Adams's opera A Flowering Tree: an Indian prince falls for the poor village girl Kumudha. Complications ensue; the least of which is Kumudha's mother thinking that the girl has been prostituting herself.
 * In The HMS Pinafore, a double version of this appears. A middle class woman loves a low class man but at the same time a upper class man is in love with her.
 * The Musical Little Me has rich Noble Eggleston and poor Belle Schlumpfert, who even have a song about how they love each other "as much as they are able" considering their differing backgrounds. The two are kept apart by Noble's mother, sending Belle off to acquire "wealth, fame, and social position." She manages to do so, but by the time she does, Noble has lost all of his. They get together anyway.
 * The musical version of Les Misérables has the revolutionary student Marius in love with Cosette (who, although technically an illegitimate child, is known only as the daughter of a rich philanthropist). Eponine is in love with Marius, but he never realizes it until the end.

Video Games

 * Disgaea loves this trope. In the third game Almaz is an extremely Unlucky Everydude Chew Toy guardsman. Sapphire is an Ax Crazy princess. There's also Rozalin (fake overlord's daughter), Adell (peasent hero). Laharl's dad (overlord) and his mom (unknown social status mage).
 * Yu (middle class) with Yukiko (Ojou) or Ai (Nouveau Riche) are possible pairings in Persona 4.
 * Muramasa: The Demon Blade: Torahime (high family), Kisuke (common ninja).
 * Mitsuru, a Mafia Princess is love interest in Persona 3. This does cause trouble as she is bethored to another in order to solidify the Krijio Group.
 * In Hatoful Boyfriend, the heroine is a hunter-gatherer barbarian who lives in a cave and dates pigeons. One of said pigeons is the snobby Upper Class Twit fantail Shirogane Le Bel Sakuya, and if she pursues him, they can end up a gender-inverted Type A version (Sakuya's family isn't too thrilled with his artistic aspirations, let alone his interest in a shabby human girl).

Web Comics

 * Beatrice and Alan in The Dreamer. Beatrice is a daughter of a wealthy Tory in Boston; Alan is a dirt poor apple farmer in Roxbury.
 * The Yaoi webcomic Teahouse centres around a brothel commonly frequented by the upper class, with Rhys and Reed implied to be particularly important members of society. The brothel owner himself is also far higher in status than Linnaeus, who was given to Xanthe's father in lieu of payment for a gambling debt.

Western Animation

 * Danny and Sam (though it's less poor/rich than middle class/incredibly rich) in Danny Phantom, though Sam doesn't really care much about her family's comically vast fortune, rarely tells anyone about it, and the series itself only occasionally draws attention to it. Despite that, it's pretty clear that Sam's parents don't exactly like her friends, and the various unexplainable ghost related hijinks that happen over the course of the series don't help much.
 * Lois and Peter in Family Guy, as shown by an early episode where Peter is at odds with her tyrannical father in order to gain his approval, which he never does. She marries him despite her father's insistence that she doesn't really love him or his covert attempts to kill Peter.
 * Dana's father is less than happy about her relationship with Terry in Batman Beyond, although it has less to do with their socioeconomic differences than Terry's criminal record.
 * Winx Club: A gender flipped version of the trope took place when Bloom learned her boyfriend "Brandon" wasn't Prince Sky's squire but the real Prince Sky all the time. It probably didn't help that she learned this during the same occasion she learned he was engaged to Princess Diaspro and that Bloom didn't know back then she's also a Princess.
 * The real Brandon fell into the trope during the royal part where Princess Stella was to be introduced into society. He was afraid his gift to her had no chance against the ones she'd get from nobles.
 * Eloise and Tag in Foot 2 Rue.
 * Asami Sato in The Legend of Korra is a Spoiled Sweet version who is a fan of Pro-Bending Street Urchin Mako before she runs into him-quite literally, she hits him with her moped and invites him to dinner to make up for it. In a twist, her wealthy industrialist father takes a shine to Mako because he reminds him of his own Rags to Riches background and offers to sponsor their team in the Pro-Bending Championships. Korra herself may qualify and is Not So Different from Asami: though she's not personally wealthy the Order of the White Lotus has provided for her every need since she was a child and gave her a lovely Gilded Cage to live in, making her something of an Ojou with the attitude of a Tomboy.

Real Life

 * Despite having been the inspiration for the Trope Namer, the relationship between singer Billy Joel and supermodel Christie Brinkley is an aversion of this trope, because despite his lower-class, "kid from the streets" origins, Billy Joel was loaded at the time he married her.
 * Elizabeth Taylor and Larry Fortensky in the early 1990s, only to be subverted in the subsequent divorce.
 * The marriage of Prince William to middle-class Kate Middleton (whose parents, it must be noted, are multi-millionaires) was of major significance to the media.
 * The Crown Prince of Nepal, Dipendra, who wanted to marry Devyani Rana, daughter of Pashupati SJB Rana, a member of the Rana clan, against whom the Shah dynasty have a historic animosity. Though the 'Prime Minister's family' doesn't seem like much of a step down from 'Royal Family' for most people, well...most people aren't royal families. As such on June 1, 2001, this lead to the Royal Family killing spree incident where almost Everybody Dies.
 * Older Than Print: Prince Justinian I married Theodora, who was an actress (basically on the level of being a whore), combining this trope with Rags to Royalty. He actually abolished the laws prohibiting their marriage.