The guy or girl do not have to be weaker or stronger than the other to not fall under this.
If the guy and girl possess personality traits that either a masculine woman or a feminine boy have, they fit.
The masculine girl does not have to be a tomboy to fit this, and the feminine boy does not have to be Ambiguously Gay to fit this either.
Examples
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It is quite possible to spot this when the guy has a pink product, while the girl has the same one in blue.
Anime, Manga, and Manhwa
Akira and Mizuki from Mayu Shinjo's Ai Ore Love Meplay around this. Akira is feminine-looking and the "princess" of his all-boys school, while Mizuki is androgynous and the "prince" at her all-girls school. However, personality-wise Akira is quite dominant and masculine and Mizuki isn't really all that boyish — though in the counted times she does show a more assertive side, Akira isn't that displeased either.
Predated by Kazuto "Towa" Sakuma and Miya from Sensual Phrase. He's a very girly-looking rock musician who dresses as a female even off-stage, she is the Bifauxnen beautician who both dates him and pretty much created his androgynous looks.
Deunan and Briareos from Appleseed could possibly count, except that Briareos is a hulking cyborg four times the size of Deunan. But their relationship follows the trope pretty straight.
Baka To Test To Shoukanjuu with the identical twins Yuuko (masculine girl) and Hideyoshi (feminine boy) Kinoshita. While Yuuko is typically feminine in traits (such as being good at cooking), her personality fit this trope because of her aggressive, prideful, arrogant, quick-to-anger, and competitive behavior. Hideyoshi on the other hand is calm, helpful, and supportive. Ironically, he is also much more popular than Yuuko, much to her dismay, because of hislooks.
Chrono and Rosette in Chrono Crusade have elements of this. Chrono is implied in both versions to be better with housework (in the manga he's shown in an apron at one point, and in the anime the Elder says he does the cooking and cleaning for him), and is much more meek and gentle (although has an extreme Berserk Button, often putting him into an Unstoppable Rage), while Rosette is loud, brash, swears constantly and was a Lethal Chef as a child. They both have their moments where they act more stereotypically like their genders (Chrono is very protective of Rosette, and Rosette is very fond of pretty dresses), but they still don't fit neatly into gender roles.
Misa and Light. While Misa looks very feminine (Idol Singer, Genki Girl, enjoys cooking, and really wants to be Light/Kira’s wife) her personality actually fits this trope: she deliberately seeks out dangerous situations and is definitely more of a risk-taker, while Light is more cautious and of the two of them she is definitely more sexually aggressive. Misa will go to any lengths to protect Light, even withstanding Cold-Blooded Torture, and she would gladly die for him.
Halle (secret service agent and karate champion) and Mello (Bad Ass effeminate mafia lord).
Re-L Mayer and Vincent Law from Ergo Proxy; Vincent is easily more emotional while Real is usually expressionless, impatient, or angry.
Sora and Yukari from Family Compo are a married transsexual couple. Here is what they look like the one time they dress accordingly to their birth gender.
Hayate the Combat Butler has the title's Hayate Ayasaki being extremely polite, humble, and skilled at domestic tasks. Mirroring him is pink-haired swordswoman Hinagiku Katsura (one of his Love Interests) who is brave, assertive, highly-athletic, and projects an aura of leadership. Simply put, he can make women around him feel their femininity is being challenged and she is cooler than any of the boys at school resulting in most of the guys andgirls crushing on her.
Each of them is a mix of traits however, and Character Development has resulted in them evening out somewhat. Hinagiku becomes less "tomboy" and more "girly", by showing that she is just as good a cook as master-chef Hayate and adores cute things, as well as focusing on her romantic side. Hayate gets to show off his determination and combat ability in addition to his dedication to duty and fulfilling his promises. Notably, he seems to like her "boyish" traits and Imagine Spots from her show that she kinda likes his "girlish" side as well.
Haikara San Ga Tooru has The Lad-ette Benio in two of these. A non-romantic version with her best male friend Ranmaru (a very feminine-looking boy who's a member of a kabuki troupe — who as much is put in the Unlucky Childhood Friend role), and a more romantic one with her arranged boyfriend Shinobu Iijyuin (who, like the below-mentioned Andre Grandier from Rose of Versailles, isn't that girly but is still more patient and sensitive than she is.)
Haruka and Kotake from Himitsu Kichi one-shot My Own Secret. She's a boyish Bifauxnen who practices judo and he's a feminine guy who likes cooking and sewing.
A non-romantic example (not counting Aoi's one-sided crush on her) is Misaki and Aoi from Kaichou wa Maid-sama!.
Sumire and Momo from Kimi Wa Petto. Sumire is an efficient, successful journalist who watches pro wrestling and Sentai anime in her spare time and is a martial arts master on the side, while Momo is a modern dancer who is fairly emotional and doesn't mind taking on the role of Sumire's pet.
Chips (masculine-looking female) and Nachos (feminine male) from Magical Nyan Nyan Taruto. They fit this more in their appearances (especially Nachos), although Nachos is definitely the more sensitive and kinder of the two.
Akira and Mai's little brother Takumi from Mai-HiME.
Mako-chan and Touma from Minami-Ke. Makoto isn't girly per se, but most of his scenes alongside the tomboy Touma feature him masquerading as a girl. In one episode, he also describes masculine and feminine traits inherited from his mother and father, respectively.
In the manga Otome no Iroha, the main siblings' grandmother comes back from the dead and forcibly Gender Bends them because of this. Her feeling was that the odds of a Pink Boy and a Blue Girl successfully marrying, let alone providing great-grandchildren, were so minute she had to take matters into her own hands.
Asuka and Ryo from Otomen, who embody the feminine/masculine hobbies side of this trope.
The second of these, Konatsu, is so feminine thanks to years of brutal treatment that he can almost be argued as transsexual, to the point that his reaction when surprised in a bath is to squeal like a girl and cover his non-existent breasts.
Ranma Saotome and Akane Tendo can be seen as a zigzagging example of this. Akane is a notoriously short tempered and violence-pronetomboy, infamous for her total lack of cooking skill, horrible at anything arts and craftsy (such as making cookie shapes, sewing, painting, etc), and not terribly good at housework. Ranma, in contrast, is capable of acting much more feminine, is very good at cooking and sewing, hates mess to the point he once forgot about burglaring a flat to clean up the mess inside instead, can actually turn into a girl more or less at will, and, according to one post-series book, actually has developed a secret enjoyment of crossdressing by the time the series ends, thanks to all the times he dressed up as a girl for whatever Zany Scheme he was pulling. On the other hand, Akane desperately wants to be more feminine and tries her hardest to achieve that, as well as having stereotypically "girly" fears (such as loathing ghost stories) and a rather idealised view of femininity (due to her beloved mother's early death andhaving been partially raised by her Yamato Nadeshiko older sister Kasumi), while Ranma is a macho jock-type who'll even go around near-naked in female form because he's that masculine.
Andre Grandier and Oscar Francois de Jerjays from Rose of Versailles. Perhaps not a textbook example, since Andre is not tremendously effeminate. But Andre is the more sensitive and people-oriented one, while Oscar is very direct and more goal oriented. Oscar is referred to as the "light," and Andre as the "shadow."
Ryuji and Taiga from Toradora have aspects of this in personality, but it contrasts with their appearance. Taiga is small ("looks like a doll") but has a brash, loud and angry personality. Ryuji has the Face of a Thug but is generally quiet and enjoys housework (especially cleaning but also cooking).
Ryunosuke from Urusei Yatsura was unwillingly raised to be the ultimate manly man by her father, and later discovers she's in an Arranged Marriage with Nagisa, the ghost of a guy raised to be ultra womanly. Though after coming back to life, he turns out to also be insanely strong, despite mostly hiding it behind over the top girly behavior.
Jung Suk Ha and Park Bong Bin from Utopia Of Homosexuality are respectively a Butch Lesbian and a Camp Gay who eventually end up together. Yes, a very misleading title.
Ito and Makoto from W Juliet. So much that it's even implied that they'll get married in drag!
Shuichi Nitori and Yoshino Takatsuki, the adolescent protagonists in Wandering Son, each prefer things associated with the opposite gender. If you think of them as their desired sexes, then this is inverted as Pink Girl, Blue Boy ... then slightly inverted again when you notice Takatsuki has pink hoodies. The anime really likes to throw around pink and blue, especially for the Nitori siblings.
Childhood friends Tsuyomaru and Hazumi from Woman in the Man, a short story by Masakazu Katsura. Mixed with Freaky Friday Flip as they switch bodies.
Your And My Secret features a soft-spoken boy, Akira Urehara and loud-mouthed girl Nanako Momoi being Body Switched into one another's bodies. Just about everyone notices how much more masculine Akira and how feminine Nanako has become, and approve.
Although there are signs of it in the book and movie, Sakura Ogawa and Kazuhiko Yamamoto's relationship is shown to be like this in the manga of Battle Royale.
Mobile Suit Gundam 0083 Stardust Memory has Mora Bascht and Chuck Keith. Although Chuck isn't all that girly, he's a fairly unassuming guy, and Mora is pretty Amazon (and head and shoulders taller than him), so this vibe is definitely present.
Ranmaru and Tsuwabuki from Binbo Gami Ga aren't a couple (although Ranmaru wishes they were) but their dynamic fits this trope well. Tsawabuki is the dutiful Promoted To Parent big brother to his four younger siblings, he is skilled at domestic chores and is pretty even-tempered. Ranmaru is the ridiculously Hot BloodedBorn in the Wrong CenturyHeir to the DojoRose-Haired Girl. Its not that Tsuwabuki is not manly but that Ranmaru is significantly MORE manly. Case in point, number of girls in their class in love with Tsuwabuki? 3. With Ranmaru? Pretty much all the rest!
Betty and Archie, from the main series, Depending on the Writer. When Archie's car breaks down, Betty fixes it. And there is even one comic where they try to enter a team surfing competition, but since Archie is too weak to carry Betty, Betty carries Archie.
Samantha and Bingo from That Wilkin Boy are Expies of Betty and Archie who fit even better. Samantha is physically very strong, while Bingo is a weak musician. This trope may explain why her father never succeeded in breaking them up or getting her to date a manlier man.
Possibly Redlance and Nightfall from ElfQuest, although the elves don't quite go for the same kind of gender stereotyping that humans do. More to the point, the siblings Suntop and Ember. When trying to get a studio to do an animated version of the comic, Executive Meddling said that you can't have a calm guy and a tomboyish girl, and this is one of the reasons the author quickly abandoned that studio.
The New Gods Mister Miracle (escape artist and acrobat from New Genesis) and Big Barda (renegade Apokaliptian gladiator) are in many ways a Happily Married version of this.
Sin City has a non-romantic variation of this in Dwight and Miho. Dwight is a laid-back everyman while Miho is much more violent and dangerous (which is definitely saying something when you take Dwight's own penchant for violent protectiveness into consideration). In fact, Dwight has expressed fear of Miho in the past and worked to ensure that he didn't piss her off.
Dale and Andrea from The Walking Dead. Dale's not feminine, but physically he isn't strong. Andrea is the sharpshooter, more energetic and take-charge personality.
Yorick and his love interest finally get together near the end of Y The Last Man. He compares them to the main couple of Moonlighting (a UST-filled detective series starring Bruce Willis and Cybill Sheperd), but takes great care with specifying SHE is the Bruce Willis equivalent.
In the comic strip U.S. Acres, Orson the pig was the feminine boy, and Lanolin the sheep was the masculine girl.
Tigress and Po from Kung Fu Panda. Tigress is a tough-as-nails warrior who lacks Tertiary Sexual Characteristics, while Po (who is also a skilled fighter, mind you) has a more cheerful and spirited personality and is an excellent cook. One-Scene WonderAction Girl Mei Ling and Crane count as well.
PJ and Beret Girl in An Extremely Goofy Movie have a lot of things in common, but they also have a few major differences in that Beret Girl is bold, aggressive, and flirtatious, while PJ is a timid, passive Insecure Love Interest. The couple invertsNo Guy Wants to Be Chased, as Beret Girl takes the lead at every step in their relationship and PJ enjoys this, but when Beret Girl was chased by Bobby moments before, she was disgusted. Beret Girl also has a significantly deeper voice than PJ, and is not much shorter, as well as going out of her way to protect him early on.
There was a short film featured on Logo that showed a Gender Flip of a heterosexual wedding. The bride wore a black pantsuit; the groom wore a white tuxedo and veiled top hat, and held the bouquet as his mother walked him down the aisle. He was also kind of short. Even among the wedding-goers, all the men wore different suits while the women were dressed more low-key.
In the movie Lover Come Back, Jerry Webster is emotional and intuitive, while Carol Templeton is logical and reserved. This is taken Up to Eleven when Webster pretends to be a chemist to trick her.
Star Wars give us a non-romantic and sibling example with Luke Skywalker and Leia Organa. Luke is a naive, sensitive farmboy who more or less fell into his role as Champion of the Rebel Alliance, while Leia is a stern, no-nonsense military commander who took charge of her own rescue mission.
At first sight, King Verence II and Queen Magrat from (among other novels) Lords and Ladies are more Feminine Boy, Feminine Girl. But when push comes to shove Magrat has Hidden Depths and can transform into an Action Girl. Verence ... not so much.
This is a central theme in the Annie M. G. Schmidt story Het Fornuis Moet Weg ("The Stove Has To Go"). It's about a girl who wants to become a carpenter, and a boy who wants to become a stay-at-home dad. They argue about it with grownups who are moving an old stove out of the house. Eventually, one of the grownups gets an idea: the stove can be seen as a symbol for the old times, when a lack of modern household appliances meant that work around the house took all day and gender roles stayed reinforced. Because of modern luxuries, women now actually have time to study and choose their own careers, so there shouldn't be a need anymore for gender roles to stay as they were. The story is considered a children's classic in The Netherlands.
Older Than Steam, even: in 1620 England, in response to a pamphlet entitled Hic Mulier, or The Man-Woman, which discussed the evils of women who dress and act like men, another pamphlet was published, Haec Vir, or The Womanish Man, stating that women would stop acting like men when men stopped acting like women.
In Jane Eyre, the title character has more moral strength and self-worth than Mr. Rochester. His feminine side comes out in the course of the relationship.
There are elements of this in the relationship between Vin (a blunt Action Girl assassin) and Elend (a thoughtful, bookish nobleman) in Mistborn. It's not completely straight — Vin does have a girly side and Elend willget dangerous if sufficiently motivated — but the trope can definitely be seen here.
Pinky and Rex about a boy whose nickname was Pinky (his favorite color was pink) and Rex, a girl who liked dinosaurs and soccer.
In the Warhammer 40000Ravenor novels, Patience Kys and Carl Thonius are described this way. Hyper intelligent, scholarly dandy Thonius is frequently referred to as a pussy, frequently by Patience herself, a vicious battle telekine. This might be entirely fair, as the novel mentions that anything short of an Astartes in full battle plate is a pussy compared to Patience Kys.
Jaime Lannister and Brienne of Tarth in A Song of Ice and Fire, aesthetically, at least. Jaime is said to be so handsome it spills over into "pretty" territory, while Brienne is known for her unattractiveness and her un-lady-like habits of wearing armor, wielding a sword, and beating the crap out people who piss her off. They form something of an uneasy Battle Couple in A Storm of Swords.
As people have observed, one of the fun things about them as a pairing is that they are very much a "beauty and the beast" couple... but which one is which changes depending on if you're talking about looks or about personality.
In a very unusual setup for a Romance Novel, Nora Roberts' Tears Of The Moon has as its romantic leads Shawn, a sensitive songwriter and pub cook, and Brenna, a feisty, tomboyish handywoman.
The main couple in Elinor Glyn's Three Weeks have shades of this, at least in terms of gender roles — Paul is boyish but virginal, beautiful and compared to Sleeping Beauty, and the Lady is older, independent, mature, compelling and in charge.
Depending on the Writer, Mara Jade and Luke Skywalker. When Timothy Zahn writes them, Luke is the sweeter, gentler one who prefers to avoid violence when possible, is always giving second and third chances, and is very open emotionally. Mara is more hostile to the world, blunt and direct and not about to let herself be jerked around, much more fiercely independent, and untrusting.
By our standards, this is the default in the world of A Brother's Price. Men being so rare they are kept protected and secluded, and internalize a set of gender roles that encourage softness, vulnerability, passivity, physical attractiveness, and affinity for the domestic sphere, while women run the world and are just about universally more assertive, daring, and calculating. A little girl in tears over a cut on her knee is even told that big girls don't cry. By his world's standards, Jerin is actually rather feminine, as he works to escape when captured and does know how to ride horses, pick locks, read, and use a gun - although he's quite stricken when he actually fires it.
Lee "Apollo" Adama and Kara "Starbuck" Thrace from the rebooted Battlestar Galactica are an interesting example of how to flip a gender dynamic: it's not so much about the way they look and dress as how they behave with each other. Apollo tends to be the softer, more introspective of the two, while Starbuck is louder, brasher, and more of an alpha than he is. Despite this, no one in-universe sees them as less masculine or less feminine for it.
Newly married Amy Pond and Rory Williams seem to have this dynamic, as Amy is an Action Girl, while Rory is a bit of a Non-Action Guy and a nurse (and while male nurses are common these days, it's still a profession that's predominantly female where he comes from).
The Doctor lampshades it by referring to them as 'the Ponds' after their marriage, instead of 'The Williamses.' Rory doesn't seem very bothered by it. According to the Doctor, it's just because Amy has an awesome surname, but he still refers to Rory as "Mr. Pond."
How I Met Your Mother does a lot of this: the men are sentimental, mild-mannered, reserved, romantic, blissfully domestic (Marshall) or kid-crazy (Ted), and are often made fun of for stereotypically feminine traits, while the women are tough, uncouth, uncultured, boisterous, insensitive, commitment-phobic (Robin), or sex-obsessed (Lily), and often engage in hypermasculine actions as comedy. However, Barney takes the aggressively-heterosexual male stereotype and drives it so far over the edge he overshadows everyone else.
However, Barney also gets his nails done and obsesses over clothing, making him feminine. And Lily is a soft-hearted romantic kindergarten teacher/artist who cries at the drop of a hat, whereas Marshall is a high-powered lawyer. So it's really played all over the place.
And then there is that one episode where they all realize that their partners are just like their parents, which has Marshall realize that Lily is just like his dad!
In Kamen Rider OOO, Shintaro Gotou is shown to be more compassionate and gentle than his female sidekick/assistant Satonaka, who hates sweets, can wield a gun with the best of them, and fights evil only because she is paid to do so.
Kamen Rider Wizard has the main character's two sidekicks: tough, gun-wielding policewoman Rinko and compassionate, klutzy, Adorkable Shunpei.
Nigel and Sydney of Relic Hunter were pretty much a straight inversion of classic adventure stereotypes. She was the action star, impulsive, fearless one and he was always in need of being rescued. Sort of uneven in that she also often got to be the smart one and the people person.
Friendship example: Fez and Donna. He and his girlfriend Big Rhonda subvert it, since she's bigger and stronger than he is but is also an awkward Huge Schoolgirl.
On Will And Grace gay Jack and straight boozehound Karen go to a meeting of an organization that promises to "cure" gayness. There they meet a married couple with a stereotypical effeminate man and very masculine woman who praise the organization. After they walk away, tipsy Karen asks "Was that two men or two women?"
Of course, Will and Grace in general subscribed to this so much that it might honestly be considered a Gender Flip of a traditional sitcom. Grace was a stereotypical sitcom man: a brash, lazy, slovenly, Big Eater who found gay porn to be exciting the same way a lot of men feel about lesbians. Will, who started Straight Gay but Flanderized into Camp Gay, was much more a traditional female sitcom character: much more calm and rational (initially,) who was the more uptight and decorated their entire apartment and did all the cooking and cleaning. In that sense, Jack and Karen could be Will and Grace Up to Eleven (he was obsessed with fashion and jewelry, she was a violent drunk.)
The X-Files was designed partly around this trope. Mulder is emotional and intuitive, cries a couple times a season, and tends to lose fistfights or drop his gun at important moments; Scully is logical, scientific, emotionally reserved, and has Improbable Aiming Skills.
When Rosie O'Donnell hosted SNL in 1994 she did a sketch called "The Tomboy & the Sissy" with her as the 'tomboy' and David Spade as the 'sissy.' They are high school outcasts who become friends and help the other become more masculine and feminine.
Exaggerated like hell in en episode of RuPaul's Drag Race, when the drag queens were tasked to give glamorous makeovers to a group of tomboyish female martial artists who have never worn makeup or high heels in their lives.
The twins Apollo and Artemis might be considered such, but only by modern standards. Apollo is sometimes thought of as a bishounen. He is the god of, among other things, music and art. He also spends a lot of time with the Muses. To classical Greeks, however, he was all man. Artemis, meanwhile, is a wild Action Girl who spends most of her time hunting in the wilderness with her Amazon Brigade.
Athene and Ares. Both Gods of war and victory, but the male Ares is something of a Glass Cannon and a serious Miles Gloriosus while Athene kicks his ass every time they fight, and is a Genius Bruiser to boot.
Ares is the personification of "manly men" fighting though. He's pretty much Dumb Muscle, while Athena fights to win. One author puts it rather well: Ares is chest banging and glory-seeking, Athena is the goddess of Nuclear War.
In Ovid's Metamorposes, Hermaphroditus and Salmacis. [1]
Professional Wrestling
Adrian Street and Miss Linda. Adrian was one of the most successful wrestlers to use the Gorgeous George gimmick, and Linda played a feminine inversion of the gimmick by being tough, aggressive and dressing in black leather.
Beth Phoenix and Santino Marella. Santino also got a bit of this when he started dating Tamina as well but that didn't really last long.
By the standards of the time, Romeo and Juliet, based on the notion that Romeo was emotional (a traditionally feminine trait) while Juliet was practical (a traditionally masculine trait).
This applies to some degree to many of the lead couples in Shakespeare's comedies; the woman is typically wittier and more practical.
This idea is played with in Macbeth, with Lady Macbeth being the more aggressive and ambitious of the two. In fact as soon as she finds out about the witches prophecy she immediately begins formulating how to kill Duncan. While Macbeth is torn with internal guilt about his feelings, she's the one that goads him into doing it by questioning his manhood and saying he has no courage. Of course, after the murder their typical gender roles are reinforced, with Macbeth turning into a kill-crazy tyrant and Lady Macbeth so wracked with guilt that she goes insane.
Tends to show up with Alistair and a female player character; consider this (possible) exchange from the sequel:
Alistair: Well, I suppose I should get back to the old ball and chain.
Teagan: You know, [she] hates it when you call her that.
Alistair: No she doesn't. Just because she killed an Archdemon... she doesn't scare me.
Teagan: You keep telling yourself that, Your Majesty.
From the Witch Hunt DLC, we have Finn and Ariane. Finn is a rather foppish mage that despises the outdoors, while Ariane is an experienced Dalish hunter. Just listen to their dialogue [2]
Aveline and Donnec in Dragon Age II. He is still a capable member of the city guard, but compared to Aveline, pretty much everyone is soft spoken and sensitive.
Seisen no Keifu has Brigid, an assertive sniper raised by pirates and sensitive, submissive horseback archer Midayle as a predestined pair; to a smaller degree she has these dynamics with her other predestined lover, archer Jamuka, who is similar to Midayle but more reserved. Another one would be Tiltyu, the TsundereBlack Magician Girl, and her shy childhood friend and local Badass Adorable Azel.
In Rekka no Ken, we have Lad-ette Vaida and gentle, honorable Heath. Kent and Farina are a borderline case; Kent isn't exactly feminine but he's somewhat shy compared to the outgoing, tomboyish Farina.
Radiant Dawn includes Rafiel, prince of the heron laguz, a race too emotionally and physically fragile to attack enemies. The woman who saved his life, to whom he is now wholly devoted? Nailah, the wolf Laguz Royal (read: absurdly badass Crutch Character). One of them wears an elaborate robe, sings like an angel, and has ankle-length golden tresses. Guess which?
Of the many possible pairings in Fire Emblem: Awakening, there's Sully/Libra (foul-mouthed Lad-ette and feminine War Monk) from the first generation and Kjelle/Brady (strength-obsessed knight and a priest who's very in touch with his feminine side) from the second.
Lost Odyssey. Possibly Seth and the husband who encouraged her to settle down and have a child. Whether or not he was an 'Action Guy' himself, we don't find out.
A Female Shepard and either Thane or Kaidan can come across like this, especially if Shepard is a hardass renegade. Shepard has to be the strongest human in existence, can drink anyone under the table, headbutts krogan like it's nothing, and generally is a stoic character. Thane and Kaidan meanwhile are sensitive and fairly soft-spoken, very moral, and the former waxes philosophical every so often. As a bonus, at the beginning of Mass Effect 2, Shepard will be clad in black N7 armour, whilst Kaidan is in the pink and white Phoenix armour.
Paragon!Shepard and Jack tends to look like this; while Shepard may be no slouch in the Badass department, he's still a calm, polite, and rule-abiding guy stacked up against the generalinsanitythatisJack.
Meryl and Johnny in Metal Gear Solid 4. When he proposed to her, she declines. Because she wanted to do that and proposes to him half a minute later.
Meryl and her partner Dave in Policenauts also qualify.
Lucas and Kumatora in Mother 3. They're not exactly a couple, but they are in the same party for half the game. Lucas has been described many times as a crybaby, and even when he seems to man up a bit later on, he still comes across as sensitive (especially with Love being his favorite thing). Kumatora is the tomboy of the group, and even has Boyish Short Hair and hates wearing dresses. And then there's her tough attitude and willingness to fight.
Homer and Edy from Valkyria Chronicles qualify, with the former being a meek, pretty little masochist and the latter a Hot BloodedIdiot Herowhocan't sing. Likewise Karl and Lynn. Although they have similar temperaments, Karl is an engineer supporting the troops while Lynn is in the front lines as a shock trooper.
In Fate/stay night, Saber has spent her entire life playing the role of king, has excellent swordsmanship skills, and is uncomfortable around her emotions, while Shirou has little combat ability but takes great pleasure in and excels at domestic tasks such as cooking. The fact that, despite this dynamic, Shirou still insists on taking up a Stay in the Kitchen attitude (at least at first) generates a lot of the What an Idiot sentiment among the fandom, which leads them to miss how Shirou's reasons behind that are... well, more complex.
Little Busters has Kurugaya and Riki. While Kurugaya is definitely feminine in appearance - very, very feminine - she's a very competent, intelligent, intimidating Action Girl who loves to dote on her cute classmates as a Cool Big Sis. Riki, being a rather short, feminine-looking, shy guy, is very much included in her 'cute classmate' category. This causes him a bit of angst in her route as he feels like he should be acting cooler for her, but Kurugaya genuinely enjoys taking care of him, and by the end he's happy with seeing her occasional cuter side.
Hatoful Boyfriend has best friends Hiyoko and Ryouta. Ryouta, the boy, is a gentle, very caring "vegetarian male" who loves cooking and frequently crossdresses in fetishistic maid or magical girl costumes for his various jobs. Hiyoko, the girl, is a tough, impulsive cavewoman who can't concentrate without red meat in her belly (mostly from animals she kills either bare handed or by smashing with weapons).
In Digger, due to the matriarchal nature of hyenas, gender roles are reversed and this arrangement is the norm rather than the exception. One character, a scrawny skin painter, has to compete with every other male in the tribe for the affection of their strongest warrior.
Last Res0rt toys with this when it comes to Jigsaw and Slick — Jigsaw's a bit of a tomboy (her main team color is light blue), while Slick's not above dressing in harem wear (and his team's main color is purple). Of course, they're not quite an Official Couple.
Ménage ŕ 3 has a non-romantic example in Zii and Gary. Zii is a promiscuous punk rocker with very masculine traits, while Gary is an Adorkable virgin at least until recently who has serious problems with being assertive.
Borderline example in The Order of the Stick. While Haley is not overly masculine, she is much more direct and goal-oriented than the ditzy and sensitive Elan.
Homestuck: Tavros and Vriska. Tavros is a sweet, shy, kind boy with low self-esteem and a great love of animals and fairies. Vriska is an aggressive, dominating Munchkin and a Jerk with a Heart of Gold with emphasis on the 'jerk'.
In Girls With Slingshots, Zach is jokingly called the "girl" of his relationship with Hazel, because he's more sedate, mature, and wants to settle down and start a family, while Hazel is a rowdy, irresponsible boozehound. Their differences ultimately prove irreconcilable.
Siblings Cucumber and Almond of Cucumber Quest: He's a sensitive mage and very much does not want to be a hero while she's an aggressive swords-woman and wants to be a hero so much that she hands over the magic orb that will bring the Big Bad into power because it sounded more fun than just keeping it hidden forever (it could also be shout-out to the kind of games the story is modeled after).
Web Original
The Nostalgia Chick and The Nostalgia Critic. She's a ladette sociopath who fights dirty and gets turned on by weakness. He's a girly, weepy psychopath who likes to be dominated.
Also done in Suburban Knights with Obscurus Lupa/Critic when she's out of character. She pulls Critic around by his tie, will teach him how to be ladylike whether he likes it or not and eventually pulls out a gun against the enemies while he's learned his "bending like a girl" lesson.
Rebecca Stone and Tacoma Narrows in Demo Reel, as she's a Lady Drunkberserker who'll genuinely try to kill you if you hurt anyone she cares about, while he's the Only Sane Man who likes the fact that he looks good in a dress and finds it better to talk things over. She and Donnie also fit the dynamic.
Parodied in this (NSFW) YouTube video, where the girl dresses up increasingly like a guy.
Should we mention that they were created by the same guy, Gunpei Yokoi, and that some consider them to be siblingsnote In either a literal or spiritual sense?
Monster High Clawd and Clawdeen, this is well played as Clawd is more Sensitive guy then Manly man. Heck, he's even afraid of his own fierce acting, little sister!
It should be noted that this is only by comparison as while sensitive, Clawd is the captain of the Casketball (basketball) team and is largely seen as The Big Guy / Big Man on Campus alongside Deuce. Clawdeen in turn isn't as masculine as she is sharp witted and fiercely protective of her friends, as this comes up when he begins to start dating her best friend Draculaura. In the past and on usual terms neither are seen this way.
There was a subtle example in an episode of Animaniacs. Charlton Woodchuck's parents meet traditional gender stereotypes at first. His father appears to be a farmer, and his mother is crying because her son is leaving home. However, when Charlton returns home his parents are sat in rocking chairs by a fireside and, in a reverse of traditional gender stereotypes, his mother is reading the evening paper and his father is knitting using a pink ball of wool.
The episode where they watch a play based on the series lampshades this by having Aang portrayed by a Genki Girl woman and Toph by a huge Boisterous Bruiser bodybuilder man (and she actually liked the idea).
Speaking of which, Sokka and Suki. Granted, it's not as extreme, but these two are respectively sensitive and tomboyish enough to qualify, though to an understandably lesser degree.
Another platonic example would be Lor and Tino from The Weekenders
In The Land Before Time, Littlefoot is soft spoken and polite. Cera is snarky and brash.
Leela and Fry in Futurama have numerous gags invoking this trope, similar to the Kim Possible example below.
Kif and Amy also have a relationship with frequently reversed gender roles for the sake of humor, including one episode where Kif got pregnant and Amy abandoned him, afraid of being tied down, only to return just in time to save the day.
Kim Possible and her sidekick Ron; she's a relentless overachiever who knows "sixteen forms of kung fu," set herself up as an international Teen Superspy, and kicks supervillain butt. He rarely fails to back her up and has his badass moments but is an easygoing type widely thought of as a loser, content to chill. Slightly mixed up in that she still fulfils gender roles such as cheerleading, while he eventually becomes a football player, but then again we see their old Halloween costumes - Kim as a cowboy, Ron as a ballerina. Nuff said.
On the villainous side of the fence, tough-as-nails Shego and sensitive and sometimes downright pouty Dr. Drakken.
Kimi and her brother Chuckie. Lil plays this with Chuckie, especially with her implied crush on him later on, but in the latter show she's grown up and changed (though she's still tomboyish).
Superjail! has Alice as the masculine woman and the Warden as the feminine boy. One episode in season 3 "Specialneeds" has Alice having to rescue Warden (who is in a full-body cast) from inmates who wanted to kill him. Justified on Alice's part since she is transsexual.
Real Life
Polish pianist, composer and Ill Boy Frederic Chopin was paired up with George Sand (the nom de plume of Amantine Dupin), a Tom Boy writer overlapped with The Lad-ette.
This is how many saw Michael Jackson and Lisa Marie Presley.
Another sensitive male musician with a harder-edged lady: Kurt Cobain and Courtney Love.
There are several animals that exist where the females are dominant over the males, such as hyenas and spiders.
Mosquitoes are an interesting case. Both genders eat nectar and fruit juices but the females are the only ones who feed on blood.
Another interesting case is the Phalarope. The females are brightly colored and go courting, while the males are dull colored and brood the eggs.
