History Main / HopelessSuitor

** Ashely towards Leon in ''VideoGame/ResidentEvil4'', even is she wasn't his mission and the president's daughter, Leon only has eyes for Ada and gently turns Ashely down when she asks him out. In ''[[VideoGame/ResidentEvil4Remake RE4make]]'' Ashely has better luck with Leon responding more mutually to her affection. It helps that Leon's relationship with Ada, as it was in the ''[=RE2make=]'', is DarkerAndEdgier rather than {{Camp}} with Leon being far more bitter towards Ada for her actions, giving Ashely a better shot.

* Krillin of ''Anime/DragonBallZ'' showed every sign of crushing hard on Bulma. She, of course, was deeply in love with Yamcha ([[AllGirlsWantBadBoys until she wasn't]]) and Krillin himself was too easily cowed to even hint to her at his interest. [[spoiler: Besides, he ends up married to another girl -- Android #18.]]

** A somewhat of a love triangle version happens with this: Rei loves Mamiya who loves Kenshiro. And it's pronounced for both of them. Rei is unable to act upon it later on as he was dying after [[spoiler: fighting Raoh]]. And Mamiya did not act upon hers because she knows Yuria is the only woman Kenshiro loves.

** Sanji gets heart-eyes for darn every girl in the series, including his crewmates.

* Fiona Frost aka. Nightfall in ''Manga/SpyXFamily'' is, despite [[TheStoic her ice-cold stoic appearance on the outside]], crazily in love with [[StudentTeacherRomance her former espionage mentor]] Twilight (currently going under the name Loid Forger). She curses the luck that kept her occupied away from headquarters at the time when Twilight was ordered to find himself a wife and child in order to infiltrate an upper-class private academy, thinking that if she'd been assigned to play the role of his wife she'd be able to win his heart and eventually marry him for real, and constantly schemes to replace the woman he did convince to marry him, Yor Forger ''nee'' Briar. Unfortunately there are several reasons why Nightfall doesn't have a chance: Twilight is [[ObliviousToLove completely oblivious to her feelings]] because of the cold, emotionless act she projects to everyone, himself included (ironically because she took his lesson to her that a spy should guard their emotions ''too'' far) and nobody likes her because of her attitude; Twilight is aware that Nightfall does not have a maternal bone in her body, making her extremely unsuited to help him look after his adopted daughter Anya (who's secretly a telepath who reads Nightfall's plans to [[EducationMama force her to study insanely hard for the sake of the mission]] and consequently is firmly ''[[ShippingTorpedo against]]'' letting her replace her beloved stepmother Yor) and is unwilling to even consider her; Yor is secretly the deadly assassin known as "Thorn Princess" who [[CharlesAtlasSuperpower is possibly the strongest woman in the world]] and who, even with all her training, Nightfall can't even ''begin'' to stand up against; and most of all, Twilight/Loid is genuinely starting to fall for Yor, [[UnknowinglyInLove even if he isn't aware of it yet]]. With all this stacked against her, Nightfall's desperate attempts to supplant Yor as Twilight's wife are more comical or even pathetic than anything else.

* ComicBook/{{Wolverine}} is this for ComicBook/JeanGrey aka Marvel Girl in pretty much every media.

** Xander Harris in the first season. He gets over it.

** ''VideoGame/FinalFantasyVII'': Johnny is in love with Tifa and utterly convinced she is his girlfriend, to her exasperation.

** In SequelSeries the ''WesternAnimation/TheLegendOfKorra'' BigFun Bolin gets LoveAtFirstSight for TheHero Korra but she only has eyes for his TallDarkAndSnarky brother Mako.

* Laurie to Jo in ''Literature/LittleWomen'', forcing him to SettleForSibling.
** Tom's pursuit of Nan in the final sequel ''Jo's Boys''.

* Thomas Middleton's ''Literature/TheChangeling'' has De Flores. He has a facial disability and his love interest, Beatrice insults and berates him constantly. He doesn't care. He goes as far as committing murder for her, but this is hardly a {{Woobie}} of any sort. His payment for one of the many schemes he devised to help her? [[SexualExtortion Exactly what he's been after all along...]]. He wouldn't take anything else despite being offered jewels and money.

* During ''Manga/TheLegendOfZeldaTwilightPrincess,'' Shad quickly falls for a troubled but very sweet barmaid that Telma just hired and seems to hit it off quite well with her. There's only one problem: that barmaid is Ilia--i.e., Link's AmnesiacLover--and Link very quickly shows up, restores her memories, and [[SheIsAllGrownUp further charms with the dashing hero he's become during their separation]]. Worst of all, [[WhyCantIHateYou Link proves just too damn inspiring and likable]] for Shad to start a CockFight with. [[spoiler:Against all odds, Shad proves the victor, since Ilia eventually realizes she can't deal with Link's violent new normal as a BloodKnight [[KnightErrant Errant]] and lets go of him without even learning that he's already found his SecondLove]].

** Randoll's mishap with women extended to its obscure UsefulNotes/{{PlayStation}}'s visual novel game starring a new protagonist Seiichiro Shiba. Randoll has a go at Shiba's love interest Rena Yuuki, which only ends with him getting beaten horribly, [[ShoutOut just like how he lost to Hayato in the TV series.]]

* ''VideoGame/PaperMario64'' was the first game to give Bowser's kidnapping Peach a more intimate motivation, regardless of how little she actually reciprocates his feelings, and the series ''really'' doesn't hesitate to hammer home just how hopeless his crush is. In ''VideoGame/SuperPaperMario'' the universe itself considers their pairing ''so against nature'' as to summon the multiverse destroying Chaos Heart!

* ''VideoGame/Paper Mario'' was the first game to give Bowser's kidnapping Peach a more intimate motivation, regardless of how little she actually reciprocates his feelings, and the series ''really'' doesn't hesitate to hammer home just how hopeless his crush is. In ''VideoGame/SuperPaperMario'' the universe itself considers their pairing ''so against nature'' as to summon the multiverse destroying Chaos Heart!

* Therkla is this for Elan in ''Webcomic/TheOrderOfTheStick''. This is complicated by the fact that she is eventually ordered to ''kill him,'' but she defies said orders and declares her love for him. Unfortunately for her, Elan is already in a committed relationship with Haley, and has no interest in cheating or leaving her, even though they're miles away from each other at the time. Therkla eventually [[spoiler: lays dying in Elan's arms, and when Elan brings up the possibility of resurrection, she asks him if he would leave Haley to be with her if she came back to life. He sadly tells her no, and she dies not wishing to be Raised.]]

* Judge Claude Frollo in ''WesternAnimation/TheHunchbackOfNotreDameDisney'' is very much this, [[NotGoodWithRejection however much he refuses to acknowledge it]]. Even if he wasn't old enough to be Esmaralda's grandfather, he is an [[HateSink absolutely deplorable character]] who won't give up on trying to either have Esmaralda for himself or kill her.

* ''Anime/{{Scryed}}'' has Scheris Adjani for Ryuho, who only sees her as a comrade and has feelings for Mimori. [[spoiler: Scheris ends up [[IWantMyBelovedToBeHappy letting go]] and [[HeroicSacrifice giving her life to save Ryuho's.]] But in a twist of cruel irony, she gets the last laugh from beyond the grave when her sacrifice is the reason Ryuho cites for NOT getting in a relationship with Mimori in the end.]]

* Judge Claude Frollo in ''WesternAnimation/TheHunchbackofNotreDameDisney'' is very much this, [[NotGoodWithRejection however much he refuses to acknowledge it]]. Even if he wasn't old enough to be Esmaralda's grandfather, he is an [[HateSink absolutely deplorable character]] who won't give up on trying to either have Esmaralda for himself or kill her.

* Judge Claude Frollo in ''WesternAnimation/TheHunchbackofNotreDame'' is very much this, [[NotGoodWithRejection however much he refuses to acknowledge it]]. Even if he wasn't old enough to be Esmaralda's grandfather, he is an [[HateSink absolutely deplorable character]] who won't give up on trying to either have Esmaralda for himself or kill her.

* Niki from ''Urotsukidouji'', whose unrequited love for Akemi drives him to [[spoiler: [[LoveMakesYouCrazy chop off his own dick]] and [[LoveMakesYouEvil turn into a rampaging monster]].]]

* In ''Manga/HajimeNoIppo'', being a Hopeless Suitor is a national sport. The main character falls in LoveAtFirstSight with Kumi, the sister of [[KnightTemplarBigBrother Mashiba]] and Kumi ends up falling for him too. Although [[TwiceShy Neither Of Them Can Spit It Out]], they basically act as a couple. Then Itagaki Manabu, Ippo's [[SenpaiKohai kouhai]] appears and falls for Kumi, while his younger sister [[GenkiGirl Nanako]] and Iimura Mari both fall for Ippo. Knowing Ippo and Kumi are made for each other (which Nanako [[ClingyJealousGirl can't seem to admit]]), Manabu later asks Mari out on the pretext that they are both "runner-ups"! Add to all this that Manabu's rival Imai Kyousuke is also a Hopeless Suitor for Nanako [[LoveDodecahedron and you have a fine little mess]]. Oh, and in the early volumes, Kimura falls for a nurse and, when he thinks this is serious, discovers she has a man. Seconds before entering the ring for a match. Ouch.

* Steve Urkel in ''Series/FamilyMatters'' is a special case in that he knows he's the Hopeless Suitor -- he's just not willing to let that stop him, hence the CatchPhrase "I'm wearing you down, baby!" His only shot at Laura was the transformation chamber that turned him into Stephan Urquelle, the epitome of smooth and cool. Steve Urkel himself managed to win Laura over in the show's last season, after some 8 years of Laura insisting on JustFriends.