Anime & Manga
- In Naruto, there's Sakura who seems to be choosing between Naruto (the Gentleman) and Sasuke (the Scoundrel).
- Alice Academy: Mikan has Ruka (the Gentleman) and Natsume (the Scoundrel).
- Shugo Chara!: Amu has Tadase (the Gentleman) and Ikuto (the Scoundrel).
- Fruits Basket: Tohru has Yuki, a stoic princely type who is always polite to Tohru, and Kyo, a hotblooded delinquent who tends to insult Tohru. She only meets Yuki a short time before Kyo.
- Cardcaptor Sakura: Sakura has Yukito (the Gentleman) and Syaoran (the Scoundrel). Played with in the end: Yukito ended up with Sakura's brother, and by the time Sakura fell for Syaoran, he was far more of a Gentleman than a Bad Boy.
- In the anime, Syaoran has Sakura (Gentleman) and Meiling (Scoundrel). Again, Sakura and Syaoran get together, and shortly before that Meiling says "I Want My Beloved to Be Happy!".
- Kitchen Princess: Najika has Sora (the Gentleman) and Daichi (the Scoundrel).
- Vampire Knight: Yuuki has Kaname (the Gentleman) and Zero (the Scoundrel). However, the roles could potentially be switched. Zero is her "safe, comfortable friend", while Kaname is the exotic one that she believes she literally can't have.
- Prétear seems to set this up between Himeno, Sasame (a good listener, explains things to Himeno) and Hayate (troubled, acts like a jerk who wants nothing to do with Himeno), especially in the manga. The anime is more... complicated. Note that she meets them both at the same time, and that in the manga they are presented as equal candidates. In the anime, well. Again, it's complicated.
- In Peach Girl, Momo spent years with a crush on the chivalrous and polite Toji, until she finally gets him. They guy helping her out on the way is Kairi, a lecherous, school-skipping bad boy she discovers she now has feelings for. Throughout the series she bounces back and forth between them, until finally she ends up with Kairi.
- Princess Tutu plays with this trope in a way that approaches Cyclical Trope levels. First, we have Fakir (the Tsundere Scoundrel) and Mytho (the Gentleman) for Ahiru. However , their roles are subverted in the second season with Fakir as the the Gentleman to the Raven Prince Mytho's Scoundrel. On the other hand, while Ahiru seems The Betty to Rue's Veronica... Rue's certainly The Betty to Princess Tutu's Veronica for Mytho. And if we bring Princess Kraehe in this, this starts all over again. Plus, Autor could be the Gentleman for Rue while Mytho is the Scoundrel.
- The one-episode Love Triangle from Kaleido Star had Sarah choosing between Kalos as the Gentleman, and Andy as the Scoundrel. Sarah chooses Kalos — in fact, she had chosen him quite a while before and that's why she had stayed in the Stage in the first place. Andy never really stood a chance, and he immediately acknowledges it.
- Another genderflipped example: In Eden of the East, Osugi (Betty) and Takizawa (Scoundrel) to Saki's Archie.
- Blue Exorcist; Shiemi appears to be liked by both the lead protagonist Rin, a Delinquent Hot-Blooded Anti Anti Christ, and his twin younger brother Yukio, an absurdly young, very polite teacher who has known Shiemi for many years.
- However, Rin is ultimately a true Nice Guy potential House Husband who is very considerate of Shiemi despite his No Social Skills while Yukio has various issues that results in him using Shiemi as a Living Emotional Crutch and is cripplingly shy in regards to Shiemi, as well as dealing with some Fantastic Racism that is partially internalized due to his heritage. In short, Yukio's Gentleman Facade hides someone who's increasingly unstable due to the pressures he gets put on him and puts on himself, while Rin's Scoundrel Facade is more from a lack of true experience at being an gentleman. So both fall under both options for Shiemi ultimately, as both are Nice Guys and both are dangerous in different ways.
- Inuyasha: As a potential love interest for Kagome, the title character is usually the Scoundrel in comparison to characters such as Hojo (although in Koga's first appearance, he sort of fills the Gentleman role).
- One example was a long-running Love Triangle with Jean Grey, Cyclops (the Gentleman), and Wolverine (the Scoundrel). Cyclops was the square-jawed, righteous leader of the team who had been with Jean since the beginning. Wolverine was the short, hairy Anti-Hero who had a smoking, drinking, and killing problem.
- The love triangle between Havok, Polaris, and Iceman has Havok as the Scoundrel and Iceman as the Gentleman. Havok and Polaris have been through hell and back together since the earliest days of the comic.
- For a brief time, Rogue, she had the polite and sincere Magneto clone, Joseph, as the Gentleman and the dangerous charming thief Gambit as the Scoundrel. Eventually, she then she has Gambit as the Gentleman, who was the traditional choice that had a lasting love for her, and Magneto, the Scoundrel, former super villain.
- In Uncanny X-Force, Psylocke had to choose between the gentleman Archangel (an honourable, decent, superhero and Honest Corporate Executive) and the scoundrel Fantomex (a roguish, mysterious, master thief and mercenary). She started the series having reignited her long-term relationship with Archangel, but was aware that his Super-Powered Evil Side might become a problem; eventually it took over and she was forced to kill him. She then dated Fantomex for a while, but eventually realised that he was manipulating her, and dumped him. After which he, too, turned evil until she gave him a psychic lobotomy.
- In Pirates of the Caribbean Elizabeth must choose between Jack (the Scoundrel) and Will (the Gentleman). Since Elizabeth chooses Will early, she ends up with him after some amount of flirtation with Jack.
- Star Wars: Princess Leia Organa has a brief love triangle with good-hearted, loyal, and friendly farmboy/Jedi Luke Skywalker as the Gentleman. Roguish, rough, and experienced Han Solo is the Scoundrel. Rather luckily (given the later revelation that she was Luke's Long Lost Sibling), she chose Han. Bonus points in Empire for Leia actually calling Han a scoundrel, and Han saying he likes the sound of it. And then teasing Leia later on by calling Lando as a scoundrel as well.
Han: You like me because I'm a scoundrel. There aren't enough scoundrels in your life.
Leia: I happen to like nice men.
Han: I'm a nice man.
Leia: No, you're not. You're...
- Subverted in Not Another Teen Movie, where Janey, having to choose between Jake (The Jock who dates her only because of a bet with his Jerk Jock buddy) and Ricky (the annoying, whiny loser of a "friend"), chooses the former, causing him to have a change of heart, while the latter remains an annoying whiny loser.
- Bram Stoker's Dracula has (although Bram Stoker's Dracula does not) a version with Mina chooses between Dracula as the Scoundrel and her much more average fiance Jonathan as the Gentleman. Dracula dies, but it is not made entirely certain that Mina goes back to Jonathan.
- The 2010 Rupert Grint movie Cherrybomb, with Michelle having to choose between the (relatively) safe and dependable Malachy (Gentleman) and the rebellious, dashing Luke (Scoundrel).
- In The Notebook Allie has to choose between Lon Hammond Jr., a dashing young lawyer who is funny, charming, sophisticated, and comes from old Southern Money or the local country boy Noah Calhoun who threatens to jump off of the Ferris wheel if she doesn't go on a date with him and constantly fights fights with her.
- In His Girl Friday, Hildy is to choose between gentleman Bruce and scoundrel Walter. Fits the trope to a t, seeing how she ends up with the man she originally chose, Walter, after divorcing him and starting her relationship with Bruce.
- As in the comics, happens in X-Men. There's a minor one with Bobby/Rogue/Pyro, with Bobby as the gentleman and Pyro as the scoundrel. The more central Scott/Jean/Logan comes complete with lampshade hanging.
Jean: Girls flirt with the dangerous guy, Logan. They don't take him home.
- This is a common theme throughout the novels of Jane Austen, of the heroine being torn between a dependable, caring man and a libertinish cad. She will always choose the former, but Austen will keep you guessing as to who it is.
- Sense and Sensibility: With Marianne choosing between Brandon (the Gentleman) and Willoughby (the Scoundrel)
- Pride and Prejudice: With Elizabeth, Darcy is the Gentleman and Wickham is the Scoundrel.
- Mansfield Park: With Fanny, Edmund is the Gentleman and Henry is the Scoundrel.
- Emma: With Emma, George Knightley is the Gentleman and Frank Churchill is the Scoundrel.
- In Harry Potter, the trope is Played With in the Lily/Snape/James triangle:
- From Snape's perspective, he was always the Gentleman: the childhood friend who dearly loved the gentle Lily despite of her heritage, and James was the Scoundrel, an arrogant showoff.
- From James' perspective, he is the Gentleman: he comes from a good family and barring his mutual animosity with Snape, he gets along well with most people. He saw Snape as the Scoundrel: someone with a negative personality and chooses to affiliate himself with unsavory individuals whose core belief system includes dsicrimination in the type of people Lily is.
- With Lily, she was somewhat mercurial with James though there were hints she was attracted to him while she did have her friendship with Snape. While James eventually cooled down and stopped being so cocky, Snape continued associating with those who would becoem Death Eaters and by fifth year, Lily ceased being friends with him. By seventh year, she was going out with James, with her choosing the Gentleman and Snape the Scoundrel.
- In Stephanie Meyer's Twilight saga, Edward is the Scoundrel, and Jacob is the Gentleman. While Jacob is more forceful and direct than the well-mannered Edward, Edward's life invited danger and death into her life, and was the choice her parents couldn't stand, while Jacob is the old friend boy-next-door who dependably offers Bella emotional support.
- Bridget Jones's Diary plays this fairly straight between Mark Darcy (Gentleman) and Daniel Cleaver (Scoundrel). The film version even describes them as "too good to be true" and "so wrong he might just be right," respectively. By the end of the books, Mark has won, although when Helen Fielding continued the column, apparently Bridget was still torn between them and even ends up having Daniel's baby. Sigh.
- In the Stephanie Plum series, the protagonist of the same name is caught in a love triangle between her childhood friend Joe Morelli and the more mysterious Ranger.
- In The Hunger Games, Katniss' original choice was not between a Gentleman and a Scoundrel, as they were both dependable people. However, as the series progresses, Peeta reveals himself as the Gentleman who cares deeply for Katniss and desires her safety, and Gale the Scoundrel revolutionist who desires to entangle Katniss in that world.
- Wuthering Heights has this as a central theme. Catherine must decide between Heathcliff and Edgar Linton— one a childhood friend with whom she shares a relationship approaching siblinghood, the other the eldest son of a neighboring wealthy family. While Catherine repeatedly asserts that she and Heathcliff are one, her family believes marrying Linton will bring them more prestige, and this is her ultimate choice. Arguably, it is this decision that ultimately kills her, as after a prolonged separation from Heathcliff, seeing him again throws her into a fatal coma presumably from sheer excitement.
- Conversational Troping in Wintersmith, when Tiffany reads a romance novel in which the heroine must choose if she wants to marry William, an honest man with two and a half cows, or Roger, who rides a black stallion and calls her "My proud beauty". Tiffany isn't sure why the character needs to marry either of them.
- From Buffy the Vampire Slayer:
- Early seasons also have Buffy's friend Xander as the Gentleman and the vampire Angel as the Scoundrel.
- While both relatively dangerous, Angel is the original man who ultimately tries to do good and be a good choice for Buffy, and Spike is the dangerous and deadly killer who was fairly remorseless through most of the series.
- Angel example: Fred had to choose between the tough, street-smart former gang leader Gunn (Scoundrel) and the bookish, nerdy Smart Guy Wes (Gentleman). (Ironically in Season 5 these roles are reversed, due to Wesley taking a level in badass and Gunn getting a brain implant). Eventually, she chose her Scoundrel, then broke up with him, turned to her Gentleman, died, became an ancient goddess, nearly killed both of them (one inadvertently), and then Wes died.
- In Veronica Mars, there's several instances of this throughout the entire series. Duncan, the Gentleman, and Logan, the Scoundrel. Piz (Gentleman)-Veronica-Logan (Scoundrel).
- Doctor Who has (or had) Amy between childhood friend and eternally devoted Rory (Gentleman) and the adventurous Doctor (Scoundrel).
- From Lost, Kate must choose between noble doctor Jack, the Gentleman, and Southern con-artist Sawyer, as the Scoundrel.
- French sitcom Les Filles d'à Côté has the flat-sharing characters of Daniel and Marc. Daniel is a suave sophisticate in a settled well-paying job with a model girlfriend. His ligger best friend and embarrassing flatmate Marc... isn't.
- The Phantom of the Opera has Christine choose between her childhood sweetheart and general Knight in Shining Armor Raoul and the insane, brooding, but more passionate Phantom. Although Word of God says that Christine loves the Phantom the most, in the end she chooses the Safe Option, Raoul.
- Romeo and Juliet: Juliet's decision between her two suitors. Paris courts her in the "proper" way, by asking her father's permission. Romeo crashes her family party with his buddies (they are not welcome there), and they create a crash of New Love Versus Old Hate. Paris definitely represents tradition, and Romeo represents passion and danger.
- BioWare is particularly fond of this trope whenever a female has more than one love interest:
- In Dragon Age: Origins, Alistair is the sweet-hearted, noble Gentleman and Zevran the sex-crazy assassin Scoundrel.
- In Mass Effect 2: Garrus and Jacob are both steady, reliable people (and Garrus is an old friend), while Thane is a dark, mysterious, broody assassin.
- In Dragon Age II, Anders and Fenris are both broody, mysterious, and lead dangerous lives, while Sebastian is a chaste Chantry boy.
- From Knights of the Old Republic II: The Sith Lords, the quiet medic and old acquaintance Mical is the gentleman, and Atton Rand is the Han Solo-like Scoundrel smuggler.
- In Penny and Aggie. Although Penny has dated both Badass Biker Rich and Nice Guy Duane, she finds that she genuinely loves only the former. Thus, when one of her hypothetical future selves urges her to use "common sense" in deciding whether to run away with Rich, this is her sarcastic response:
Ooh, what if he doesn't make six figures? Ooh, what if I want kids and he doesn't? Whiiiine. I better hook up with the nice class president!
- Disney's Pocahontas presents a lifestyle choice with the steady home-building Kocuom, choice of her father (the Gentleman), and the native-killing foreigner John Smith (the Scoundrel). She does not end up with either, as Kocoum dies and John Smith must go back to England, but her choice lies with John.
- In King of the Hill, Nancy Hicks-Gribble has been carrying on an affair with the Scoundrel, John Redcorn, while married to her Crazy Survivalist husband Dale (the Gentleman).
- In Thundercats 2011: Lion-O (Gentleman) has a crush on Cheetara which makes Tygra (Scoundrel) jealous. She chooses Tygra.