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Anime and Manga
- Tatewaki Kuno from Ranma ½. Both of the girls he obsesses over can't stand him and clobber him every chance they get.
- Played for comedy, Kyonosuke Kaoru is this for Yukiji Katsura in Hayate the Combat Butler. She actually seems to have a fondness for him, but he seems to think he needs to sweep her off her feet which causes her to reject his advances.
- Played with in Fables with the character of Prince Charming himself; he genuinely is very good at starting the relationship he wants, but he's very bad at maintaining it. He has been married to Snow White, Sleeping Beauty and Cinderella, and in every case the woman fell head over heels for him (and he reciprocated passionately, if unsustainably) only to divorce him when he seduced some other woman who had taken his fancy. By the time of the main story, his long-term failings are well-known (to himself as well as potential partners,) so both he and any girl he seduces treat it as short-term. Interestingly, this ability to start things but not sustain them carries over into non-romantic pursuits as well; his campaign to charm people into electing him mayor is extremely successful, but he's completely out of his depth when it comes to the actual work or running Fabletown.
Films — Animated
- Gaston from Disney's Beauty and the Beast thinks he's the hero, and that Beast (Jerk with a Heart of Gold) is a monster who wants to get his claws on Belle. But in the end, it is clear that the opposite was true.
Gaston: You know, Belle, there's not a girl in town who wouldn't love to be in your shoes. This is the day your dreams come true!
- In the stage version, he even has a song called "Me", extolling his greatness and how lucky she is to be the object of his affections. (This is in addition to "Gaston" from the film, where the rest of the town extols his virtues, although his plans to marry Belle only come up in the reprise.)
- And as egotistical as he is at the start of it, he gets worse later on in the movie when he goes into full-on Yandere mode threatening to throw her father into the asylum if Belle won't marry him and trying to kill the Beast who he feels is an obstacle to what he sees as his. Asshole indeed.
- Jean-Bob from The Swan Princess, albeit because he thinks he's a Frog Prince who needs a kiss to turn back to his non-existent human state.
- Hal from Megamind thinks that Roxanne will automatically swoon into his arms after he gains superhero powers and shows them off to her. When she doesn't and displays interest in another man instead, he snaps and becomes a full-blown villain.
- Roland from Strange Magic who'd might be able to pull of an Elvis flavored version of Prince Charming except for the girl he's trying to woo was the girl he cheated on right before their wedding, meaning she's not having any of it.
Films — Live-Action
- Biff Tannen from the Back to the Future trilogy.
- Henry Crawford of Mansfield Park — self-affirmed Ladykiller in Love...who runs away with the already-married cousin of the girl he considers himself engaged to (regardless of said girl's thoughts on the matter).
Henry: I will make her very happy, Mary; happier than she has ever yet been herself, or ever seen anybody else. ...Yes, Mary, my Fanny will feel a difference indeed: a daily, hourly difference, in the behavior of every being who approaches her; and it will be the completion of my happiness to know that I am the doer of it, that I am the person to give the consequence so justly her due. Now she is dependent, helpless, friendless, neglected, forgotten.
- Walter Hargrave of The Tenant of Wildfell Hall:
"By all means, leave him! cried he earnestly; But not alone! Helen! Let me protect you!""Never! while heaven spares my reason, replied I, snatching away the hand he had presumed to seize and press between his own. But he was in for it now; he had fairly broken the barrier: he was completely roused, and determined to hazard all for victory.""I must not be denied!" exclaimed he, vehemently; and seizing both my hands, he held them very tight, but dropped upon his knee, and looked up in my face with a half-imploring, half-imperious gaze. You have no reason now: you are flying in the face of heaven's decrees. God has designed me to be your comfort and protector - I feel it, I know it as certainly as if a voice from heaven declared, "Ye twain shall be one flesh" - and you spurn me from you -""Let me go, Mr. Hargrave!, said I, sternly. But he only tightened his grasp."
- Lord Arlington from Louisa May Alcott's The Inheritance, who finally experiences a Heel Realization long after causing the heroine plenty of grief with his unwelcome advances and repeated marriage proposals.
- Mr. Collins from Pride and Prejudice - though his motivation is less knight-errant than greatest village parson ever, to the great Lady Catherine de Bourgh.
- Geis in Against a Dark Background.
- Brian de Bois-Guilbert in Ivanhoe just can't seem to wrap his head around the fact that "Marry me, and I'll save your life; refuse, and I'll let you die" is something villains, not heroes, do.
- Genderswapped - because gender roles in general are given a thorough Stereotype Flip - in A Brother's Price. Kij Porter thinks she can have Jerin eating out of her hand, but... he can't stand her. It doesn't help that she insults his family and condescends to him. She kidnaps him later.
- The wealthy Jim Taggart of Atlas Shrugged loves promoting how he heroically raised Cherryl from the slums by marrying her... while psychologically abusing her until he drives her to suicide. He likes the fantasy, but he likes the power he gets from harming others just as much.
- Noah's Arc: Millionaire rapper Baby Gat is this to Noah, trying to rescue him from his "mundane" life.
- Ground Floor: Harvard is convinced that Jenny will eventually realize that she is truly in love with him, ignoring the fact that she only sees him as a friend and that everyone is genuinely put off by his attempts at wooing her.
- Jonathan Coulton's "The Princess Who Saved Herself":
Philip: Hey, beautiful. Prince Philip.
Princess: Oh, hi... Philip.
Philip: Yeah, we met at the ball. I was the handsome one. I was wearing a...
Princess: Hey, Philip. Tell me if this sounds like a phone hanging up. (hangs up)
Philip: Yeah, it totally does! Hello?
- In the Foster's Home for Imaginary Friends episode "Frankie My Dear", an imaginary Prince Charming is left at the home to be adopted, but falls in love with Frankie and tries to woo her. Unfortunately, he has to compete with Mac, Bloo and a pizza boy, all of whom have a crush on her as well. They all crash Frankie's dinner date with her actual boyfriend who turns out to be a jerk.
- Zap Brannigan in Futurama.
- Pierce Thorndyke III, in Beverly Hills Teens.