This is when Bob (this character is usually male, although female examples do exist) is madly in love with Alice. Alice doesn't seem too interested, so Bob keeps trying, hoping that she will change her mind.
This can play out in one of two ways:
If Bob and Alice are strangers or distant acquaintances when he falls for her, after the first confession that was turned down, he will show his affection in more and more spectacular ways to prove his serious intentions. Sometimes, the people around them will expect that Bob will eventually get together with Alice. Once Bob's displays of affection convince Alice to change her mind about him and give him a chance, the two will be portrayed as a normal couple. This is frequently used by romantic comedies or other shows/movies where they want to keep the audience asking Will They or Won't They?Low-Key Yearning:
If Bob and Alice are either long time friends, or strangers who just got into a Just Friends relationship, Bob will take a more low-key route. Bob will likely begin by saying that he has his hopes for a more serious relationship, and he hopes Alice will eventually feel the same. He's content to be Platonic Life Partners until that time comes. From here, he may remind her of his unrequited love every time he sees her, or he may never mention it again. Alice might refuse the Relationship Upgrade because she doesn't want to ruin this friendship, or else believe that Bob just has a schoolboy crush he'll get over. If Alice is in a relationship, Bob might try to accept it for Alice's sake. If Bob dates someone else in the interim, this may make Alice have a Green-Eyed Epiphany and create a Unrequited Love Switcheroo.
In traditional straight examples, as long as Bob is an honestly Nice Guy, or at least a decent guy, both of these two attitudes are usually expected to result in success. Due to the Rule of Romantic, Alice will always realize over time, that she really happens to love him back.
In some recent works, a more cynical take on the trope might be used to point out some ways this type of thinking could backfire, resulting in a Deconstructed Character Archetype. Spectacular displays might irritate the object of their affection by treating them like a video game sidequest, where more gifts and displays of affection will equal more attraction. It can also have implications of a Stalker with a Crush situation, if Alice truly dislikes or fears Bob. And the low-key yearning sort might be portrayed either as a Manipulative Bastard, for whom the whole long-term friendship is just a means to an end, or tragically mistaken for not recognizing that Alice still only feels like they're Like Brother and Sister and reacts with extreme Squick to romantic gestures. And both types might be examined to show that Bob actually feels that he's Entitled to Have You and thinks that, since he's a "nice guy" who is interested in Alice, Alice is morally obligated to date him.
This recent shift to more harsh portrayals is in part due to the usual cycle of tropes and part to media trying to avert the the implications that Men Act, Women Are, and that a romantic resolution depends solely on the man's determination.
Gender Inverted variations often occur, typically with a natural-looking, down-to-earth woman who is determined to win over the male friend she secretly loves, hoping he will eventually learn to appreciate her wholesome charms (often contrasted to the flashier appeal of a high-maintenance, unworthy gold-digger). For example in the Harem Genre, girls often recognize each other as "rivals", and treat the whole situation as a race where the most determined girl "wins" the protagonist's heart. Also, more traditional romantic stories, written by either men or women, might give a woman the same behavior, suggesting that these writers (and their audiences) find something inherently romantic about that kind of dogged determination, even without the Unfortunate Implications of a gender's inherent domination.
See also Extraverted Nerd, Just Friends, I Want My Beloved to Be Happy, Nice Guy, and Romantic Runner-Up. This heavily relies on the Hard Work Fallacy.
Compare with the less sympathetic Stalker with a Crush, Mad Love, and Abhorrent Admirer.
Contrast Cannot Spit It Out, where the person is incapable of expressing their romantic interest even once, let alone over and over again.
Please keep the Real Life examples limited to those that examine the Dogged Nice Guy as a trope.
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Anime and Manga
Keisaku Satou from Shakugan no Shana is this for MargeryDaw. She pretty much commandeers his home, drinks his home dry of alcoholic beverages daily, and generally tends to be really high maintenance. However, he keeps his mouth shut and helps her (as a Mission Control) with her job as a Flame Haze (even after his buddy Eita does an Opt Out) due to having had a crush on her that turns into full blown romantic attraction. She tries to keeps him at arms length with her Dark and Troubled Past, but this epically backfires, and by the end of Season 2 of the anime, she's rather aware he hasn't given up. In the final season, she finally breaks down and reciprocates his feelings.
Likewise, Sakura was also a female version towards Sasuke in Part 1 before she gets Character Development too.
Chapter 539 provided us with an unknown ninja who is infatuated with Sakura, going as far as previously writing her a love letter, and attempting an "If I don't make it..." before being (very politely, at least in the anime) turned down by her. Mind that they were in the middle of a war and it was bit inappropriate at the time.
Winner Sinclair in Karin. Not only does he fail to notice that Karin isn't interested in him, he also doesn't notice that she's a vampire and that her best friend is interested in him.
Toris/Lithuania of Axis Powers Hetalia is a good example of this... while he is a kind person who wouldn't deliberarely hurt anyone, he refuses to see that his crush Natasha/Belarus hates him because her rather "special" crush is Yandere for Lithuania himself. So she breaks all his fingers in retaliation, but Lithuania refuses to notice it.
Back when Italy was Chibitalia, the Holy Roman Empire was this to him. Chibitalia was scared of him at first, but eventually returned his feelings.
Many fans of Ranma ½ regard Mousse to be this to Shampoo. Other fans wonder if the guy will get to the point where Shampoo will not be obliged to kill him out of hand once she gets over Ranma and finds someone willing to return her (distinctly non-ambiguous) affection.
Two moments question Shampoo's feelings for Mousse in the anime. The 2nd movie she's arguing against her captor that she has no feelings for Mousse then rescues him anyway. And in one OVA she's given the reverse necklace which reverses her feelings; Mousse finally thinks it's his chance since she'll love him now only for her to scream how much she hates him and beat him nearly to death.
And then there's Ryoga, who is depressed over the fact that Akane sees him only as a friend and nothing more. Or rather, he would be a Dogged Nice Guy if it weren't for his bad case of Cannot Spit It Out. In the manga, he eventually acquires a femaleadmirer (who even likes his curse) in Akari Unryuu, and by the end he drops his romantic pursuit of Akane entirely in favor of her. (Making him the only character in the series to break out of the status quo... although he never actually confessed to Akane, either.)
Morinaga in The Tyrant Falls in Love has stuck by Souichi's side for five years in the hope of having his feelings returned someday, despite Souichi being a homophobe. (Granted, he spent most of those five years concealing his feelings because of the homophobia thing, but he's had enough of hiding them by the fifth year.) Souichi even compares Morinaga's behavior towards him to a dog following its owner, though he's showing signs that he actually doesn't mind Morinaga's dogged pursuit of him.
Morinaga is an unusual example of this trope because he actually rapes Souichi (at the beginning of the story, setting off the plot). Normally this would disqualify him from DNG-hood, but his behavior afterword still counts as this trope, only new he's become more of The Conquerer as opposed to the Patient Friend.
In Lovely Complex, the main character Risa becomes a Dogged Nice Girl when she realizes her crush on the lead male Atsushi. It doesn't help that all of her friends are constantly encouraging her on in her pursuit of him. Though to be fair, she's not always lovey-dovey to him...
Megumi "Nodame" Noda from Nodame Cantabile is another female version, after she falls in love with the ridiculously talented Chiaki. She needs no encouragement though...
Gender-flipped and (possibly) non-romantic example: Sasada Jun from Natsume Yuujinchou, a Muggle who repeatedly attempts to make Natsume admit that he has supernatural powers and generally shows a very large amount of interest in him.
Used in most installments of the original UC Gundam saga. A recurring theme throughout is that of the Dogged Nice Guy utterly failing in his pursuit because the woman has already pledged herself to a man with a much more open/stronger personality, or one or more participants in the Love Triangle wind up dead. Worst of all is probably the sad, sad tale of 13-years-old Hathaway Noah of Mobile Suit Gundam: Char's Counterattack, who can't even let go after the girl (Quess) is dead. In the sequel novel, Hathaways Flash, he leads a resistance movement against The Federation to avenge her, fails spectacularly and gets executed (under orders from his own father, no less, who doesn't even know he's a terrorist!). When he meets Quess in the afterlife, he finds out it was all for nothing because she never even liked him anyway. Ouch.
This is basically Shi Ryuuki's approach to his relationship with Kou Shuurei in Saiunkoku Monogatari. To Ryuuki's credit, it's less that Shuurei isn't interested in him personally and more that she has goals which preclude the thought of romance entirely; even more to his credit, he really does genuinely want her to be happy, which is why he doesn't, as The Emperor, simply command her to be his consort and remain at the palace. But all things being equal, he'd prefer that she be happy with him, and he's prepared to wait forever, constantly giving her gifts and trying to think up ways to win her over.
Angel Densetsu: Kuroda is a Dogged Nice Guy to Ryoko (who beats the crap out of him every few chapters), but he's clearly intended to be annoying and the whole thing is Played for Laughs.
Shirley from Code Geass is a Dogged Nice Girl towards Lelouch, and although he does like her as a person, as far as romance is concerned she doesn't have a chance. That is, until they start dating in the second season at the end of the Cupid's Day Festival. Naturally, this was Milly's idea.
And Rivalz to Milly, though he's every bit as hopeless.
Kitagawa Jun in the 2006 version of Kanon. Kaori is very aware of his efforts, but uses it to her advantage, making him her personal bagboy when she goes shopping.
Keima takes a page out of the Visual Novel book and turns into one of these during The World God Only Knows. Justified because if he isn't dogged enough to get the girl, he loses his head.
Joshua Lundgren of GUN×SWORD is a sweet, smart, polite young man (despite his social awkwardness). Wendy immediately recognizes that he's "nice," but she's already so smitten with Van that she doesn't seem to realize that Joshua has a crush on her.
The very, very flirty but loyal, kind and patient-when-it-counts Dee towards Ryo from FAKE.
Yuusuke from Tenshi Ni Narumon tries to win Natsumi, his aloof classmate's heart to no avail, and at least throughout the first season, she generally treats him like a crap. Likewise, Noelle is this for Yuusuke.
Also, Raphael can be considered this (mixed with Chivalrous Pervert) for Mikael. Although it is a little more complicated in their case, because they really do love each other, but let's just say that Mikael has some serious problems.
Genzo of Cheeky Angel: arguably the king of conquerers. Asking his Megumi to marry him repeatedly, replying to all preference questions with "Megu," dressing in drag, climbing an elevator shaft, tracking down her enemy to break into his house and patiently wait for the guy to come home... to name a few.
Firo in Baccano! is this to Ennis...he declares Love at First Sight and then proceeds to wait patiently for more than fifty years for her to agree to marry him. Good thing both of them are immortal. Eventually she does return his feelings.
Nika from the second season of Darker Than Black. He starts to date Tanya in the first episode, then she becomes a Contracter out of nowhere, and then breaks up with him. He follows her to try to convince her to come back, only for her to manipulate him and beat the crap out of him with her powers. Then when he catches up to her again, all bloodied and bruised, he says that he still loves her.Then she kills him without a thought.
Norio is portrayed like this, and though he does have the traits, him being a Lolicon and incredibly annoying don't really garner much sympathy. He is at least 18, while Suou (who he obsessively chases after he falls in Love at First Sight) is 13. Not only does no one find this weird, but his pursuit of Suou becomes rather creepy. The show tries to drum up sympathy for him with his mother being a Contractor, and his dad being depressed after she left him. His presence doesn't really add much to the story, but Suou herself even commented that he was just like Nika. Except he wasn't. At all.
Tatsuya Tsugawa displays a low-key yearning for Action GirlSeine in Hekikai No AION. He tries to be her Living Emotional Crutch, always remembering her that he'll always be there for her, worries about her dangerous methods of hunting and tries to make her smile at least. She calmly said to him she doesn't correspond his feeling but he said he doesn't care and keeps trying, even after 4 years.
Takuto to Mitsuki in Full Moon o Sagashite. At first he was I Want My Beloved to Be Happy but after finding out this was impossible unless Mitsuki dies TOO, he decides to confess to her. She rejects him at first but he continues to protect her til the end. Fortunately, it finally pays off.
In Bokura no Kiseki, Moto has been in love with Hiroki since middle school, and for a long time he Cannot Spit It Out. However, he becomes this when he confesses in chapter 6. Since they're in the middle of a crisis situation, he doesn't get a reply for a good while, but she ultimately rejects him, with the implication that she's probably in love with the protagonist, Harusumi. However, he later says he's glad he told her how he felt, and he doesn't seem ready to give up.
David Qin in Strangers in Paradise seeks Katchoo out on a more or less daily basis, even though she explains repeatedly (and violently) that she's not interested in men. It's revealed later on that his sister Darcy sent him to spy on Katchoo and Francine. She relents after he helps her and Francine through some rough times, and he moves in with them.
Often, Archie towards Veronica, and similarly Betty towards Archie.
Luann: Brad is this most of the time, chasing crushes Diane and Toni- especially true for the latter. Though at times he's been shown as angry and loudmouthed towards his sister, he's largely completely sympathetic the entire time.
In Pocket God, Nooby has a crush on Sun and was the first of the tribe to be nice to her. However, she ended up with Ooga, Nooby's best friend. This made Nooby feel unloved by both, but he got over it once Ooga apologized for neglecting him.
Midnight from A Pleasant Surprise, is definitely this. It pays off for him in the end when he gets with Fluttershy.
Greece from Axis Powers Hetalia often a low-key yearning for Japan in fanworks, sometimes to the point of waiting over a hundred years for Japan to return his feelings, although it's clear in most of these fanworks that Japan does like Greece back and just has a bad case of Cannot Spit It Out or Oblivious to Love. Or that both of them are Twice Shy.
Sometimes Japan's adoptive sister Taiwan is depicted the same way, acting cheery and sweet to him but deep down also expecting him to like her back.
Spain also has shades of this in some Spain/Romano fanworks. While Romano is shown as a Tsundere in Spain/Romano fanworks, he might switch to this trope in Romano/Belgium ones.
Korea is depicted as this in pretty much all China/Korea fanworks. Some of these fanworks actually give a tragic spin to this trope by depicting Korea as being fully aware that China doesn't return his feelings or just finds him annoying and knowing deep down that throwing himself even more at China will not change this, but that he can't bring himself to give up hope that someday, somehow, China will eventually love him back.
According to some fanfics, James Potter and Lily Evans from the Harry Potter universe fit this trope well. It seems to be pretty solidly there in canon, though. When we see James asking Lily out in their fifth year, not only does she turn him down, they're both acting like this is hardly the first time she's had to reject him. We're later told that they didn't start going out until seventh year, so that's at least two years of James dogging persistently after Lily, since we don't know when he first started asking.
There's a subversion there as well. James was a Jerk Jock in their fifth year, and a bully on top of that, which is one of the reasons Lily wouldn't have anything to do with him. It was only when he got over himself that Lily reciprocated. (Not to mention that her other suitor was Severus Snape, a mix of Unlucky Childhood Friend and Stalker with a Crush who lost his chance via greatly wronging Lily in the worst way possible.)
Takato acts like this towards Rika in the Tamers Forever Series. Even if it's downplayed due to the fact that Takato never tells Rika about his crush, His selfless devotion to her is truly a thing of awe. Even after she cruelly mocks him, he will still be there to help her, without ever once coming across as an Extreme Doormat.
Subverted in Megamind. Hal seems likely to go the "spectacular romantic displays" route at first, his attempts to win Roxanne's attention are sympathetic or creepy even at the very beginning. Either way, it quickly becomes apparent that he is, at best, highly insensitive to her actual feelings, not to mention mildly delusional. In the end, far from winning her over, his childish attitude toward Roxanne contributes to his proving to be the villain of the piece.
Cloverfield, of all places: It's made clear early on that Hud has feelings for Marlena, even though Marlena isn't particularly interested and brushes him off more than a few times. As the movie progresses, however, they start to get along better, reaching a head when Marlena attacks one of the parasites that was trying to drag Hud away, getting bitten in the process. She starts to warm up to him when he helps treat her wound, but it all ends badly when the bite makes Marlena die in an incredibly disturbing and sudden way. It's driven home and made all the more wrenching that she asked Hud for help first when she starts rapidly worsening, rather than her best friend.
To a certain extent Knox Overstreet from Dead Poets Society in his subplot with Chris. It is unresolved whether they wind up together or not by the end.
Subverted by Private Zoller in Inglourious Basterds. He acts exactly like a romantic comedy protagonist, as this trope demands, but, of course, there are a few problems. Not least of all is the fact that, well, Shoshanna's (secretly) Jewish, she's already dating a black man Marcel, and he's a freakin' Nazi! To squick us out even more, he hero-worships the man who slaughtered her family; both the audience and Shoshanna know this from the second scene we see him in. When she finally manages to get through to him that there's no way in hell that she'll ever be interested in him, he stops being so nice... Also, he uses his strong-arm Nazi position to force her on dates with him and to position himself at the theater she works in. Very very not nice.
Patrick Swayze's main character in Ghost sang "King Henry the Eighth I am" to his love interest Molly over and over until she agreed to go out with him. I'm not sure, but in real life that behavior is probably more likely to land you a restraining order...
Well, it depends on whether she actually felt harrassed and uncomfortable about it...a guy who sings a song to you over and over may very well come across as more hilarious than threatening.
Subverted in Snow Day; Dogged Nice Guy Hal, after finally getting the girl, realizes how Lane, who had appeared doomed to be an Unlucky Childhood Friend, feels about him, and somehow manages to let the original target girl down without coming across as a massive Jerk Ass.
Nick from Youth in Revolt is this in spades; at the beginning of the movie, he has a line of narration where he says that in real life, the nice guy never gets the girl. He actually does get the girl—well, sort of. She likes him, but she'll only be with him if he can find a way to leave his hometown to be near her. His means of getting himself to her are creepy and occasionally manipulative of others, and the worst one has nothing to do with his Bad Boy alter-ego.
In Caveman, the protagonist Atouk (played by Ringo Starr), is this to the villain's superficial girl Lana. Subverted in the end, since he literally dumps her on dinosaur poo and goes for the dogged nice girl Tala.
Both Life Is Beautiful and The Tiger And The Snow from Roberto Benigni have this, as an over-energetic male protagonist (played by him) engages in stalkerish behavior to get the woman he is in love with.
Deconstructed in Good Luck Chuck. Terrified of losing Cam due to the curse, Chuck goes into full Type A mode, which creeps Cam out so much that she breaks up with him for stalkerish behavior.
Fred Astaire played a lot of characters like this, most notably in Top Hat and The Gay Divorcée, both of which feature him chasing after Ginger Rogers' character in a car the second time they meet.
Jane in 27 Dresses is the Patient Friend variety for her boss, George. Subverted in the end: as when they finally kiss, she "felt nothing", and she realises that she's fallen in love with Kevin, the reporter, instead
Donald Morton in Mozart and the Whale.
Dil Se features the male lead Amar chasing a Broken Bird terrorist named Meghna all over the country, trying to win her affections. It does not end well.
Tora-san from the famous Japanese movie series Otoko wa tsurai yo is very much this.
In another Batman related example, Bruce Wayne thinks his eventually getting together with Rachel Dawes in Christopher Nolan's The Dark Knight Saga is a foregone conclusion. They've been friends for years and once she learns the truth about his double life as Batman he seriously thinks that she'll wait for him to finish being Batman as long as he remains true to her in his heart and all that jazz (she does give him that impression at the end of the first film after all). In The Dark Knight however Rachel moves on to Harvey Dent but Bruce seriously thinks Dent is just a placeholder while Rachel waits for Bruce to finish up his work as Batman, but Rachel is clearly more into Dent than Bruce and in the end she does realize that and tells Bruce as much in a letter - only to get herself blown up and for Alfred to burn the letter believing it's for the best and hoping Bruce will eventually move on. Unfortunately, Bruce spends 8 years moping over Rachel even after the truth finally comes out in The Dark Knight Rises before he settles down with Selina "Catwoman" Kyle in Italy.
Demetri Martin's character in In a World... plays this very straight.
Max from Design For Living "didn't get to first base" with Gilda, but has been hanging around her for five years as her "friend", carping with disapproval about any other man she happens to date. She finally caves and marries him after leaving Tom and George.
Gilbert Blythe is the epitome of the second variation. He makes a badly-time comment about Anne's red hair and falls for her the instant she smashes her slate over his head in retribution. However, Anne holds this grudge for five years or so, in which time he tries valiantly to convince her he's not the jerk he originally come off as. Once they're friends, he gently implies at times that he wants to be more than just friends, though since Anne is oblivious to both his feelings for her and her growing feelings for him, it goes over her head. He continues to try and be her friend even after she shoots down his marriage proposal and after she dates another man for nearly two years. It takes a near-death experience for Anne to realize she's in love with him, the poor guy.
A clear example with Silvius to Phoebe in the Bard of Avon's As You Like It.
The Beast of "Beauty and the Beast" asks Beauty to marry him and keeps on doing so even though she keeps on rejecting him every time. Granted, he needed someone to fall in love with and marry him for his curse to be broken, but it's taken for granted that Beauty will eventually realize that he's actually a Nice Guy underneath his monstrous exterior and finally agree to marry him. This, coupled with the possible Abduction Is LoveUnfortunate Implications, can make this fairy tale unintentionally creepy if mishandled.
Joseph Heller's Catch-22 brings us Nately, who is madly in love with a prostitute who couldn't care less for him (and would much rather get some much needed sleep), but sticks around him anyway because, well, she's a prostitute and he pays her to, hoping all the while that eventually she'll come to her senses and reciprocate his affection. Eventually she does, after finally getting some shuteye, and Nately dies almost immediately thereafter.
Subverted in the second Dark Swan novel, Thorn Queen: Leith is obviously attracted to Eugenie, and spends a lot of his time trying to win her affections, eventually confessing his love for her, believing she feels the same. When she makes it clear that she simply isn't interested, he leaves, brokenhearted. Later, however, she gets captured and drugged for Leith's benefit, and he proceeds to rape her repeatedly - genuinely believing his actions to be out of love and outright denying that what he did was rape. Thankfully, he gets his comeuppance eventually...
Nicely played with in Terry Pratchett's Going Postal. We are not sure whether Moist will get Adora Belle Dearheart. He will - they are engaged as of Making Money. It's a particularly odd example of this trope because Moist is a consummate con artist, and so he's very, very used to putting on crazy shows. His feelings for her are genuine, but he's put just as much effort into performances aimed at swindling people. Not only that, she was an accidental victim of his in the backstory, so she has a very, very good reason to not trust him.
Dante Aligheri to Beatrice; not as much in (possibly) real life or story (The Divine Comedy or La Vita Nuova) than in scholarly letters.
Aubrey Takes Flight toward Annie Little Hawk in Gives Light.
Ben Hanscom to Beverly Marsh from Stephen King's IT, the novel is very explicit on the intense crush Ben has with her, later lampshaded when adult Bill and Beverly have sex together and they both wonder why it's his arms she falls into instead of Ben's. The Film of the Book ends with Ben becoming a Victorious Childhood Friend, with the two of them on their way, later getting married and having children (breaking another "Losers" curse). In the book, they're together when they visit Mike one last time, and decide to drive back to Nebraska instead of flying, so they can get to know each other as adults. It's a fair assumption they end up together. Richie's hinted crush on Beverly in both the book and the film are more suggestive of this trope. He knows that Bill will always be the one who "gets the girl," not him.
In the Kate Daniels series, Raphael is a Dogged Nice Guy to Andrea, pursuing her for months despite her protests. Justified in that Andrea is a Master of the Mixed Message, giving lame excuses for rejecting him, keeping his obnoxious gifts, and becoming visibly aroused when he flirts with her. Subverted when Raphael finally gets sick of it and tells Andrea to either give him a chance or stop leading him on.
Light And Dark The Awakening Of The Mageknight: Justified. Danny has good reason to believe Sabrina likes him back (because of her comment on how dragons often hide or evade such things) but refuses to acknowledge it due to their respective roles. He fully intends to change her mind in the sequel.
Almanzo Wilder's courtship of Laura Ingalls initially takes this form. It takes her a while to figure out why he's seeing her home from church and driving her to and from her teaching job every weekend, and when she does, she panics a little. She tells him she's only riding with him because she wants to go home at the weekends, and that he doesn't need to feel obligated to keep doing so. The next weekend it's forty below zero and getting colder fast, and she's certain he won't come get her, but he does. When her job's over they go sleighing every weekend, and she comes to decide being courted isn't so scary after all.
Dorothy L. Sayers' Lord Peter Wimsey, though not by any stretch of the imagination a loser and rather more self-aware than most, otherwise fits this trope nicely in his wooing of Harriet Vane.
Lord Peter: I shall, with your permission, continue to propose to you at decently regulated intervals — as a birthday treat, and on Guy Fawkes' Day and on the Anniversary of the King's Ascension. But consider it, if you will, a pure formality. You need not pay the slightest attention to it. Harriet: Peter, it's foolish to go on like this. Lord Peter: And, of course, on the Feast of All Fools.
Black, one of the protagonists in My Name Is Red probably falls into this category.
Homer/Sonny in October Sky / Rocket Boys is a Dogged Nice Guy to Dorothy Plunk. He eventually gives up, though, when he sees her on a date with his brother, although he never quite loses his feelings for her.
Both Kenny Showalter (towards Mia) and Boris Pelkowski (toward Lily and Tina) are featured in The Princess Diaries books. Boris succeeds and Kenny does not.
Quite a few P. G. Wodehouse characters. Psmith is a good example, at one point flat-out admitting to his target that he's not expecting her to accept the proposal. He's just hoping she'll add his name to her list of options. It works.
In Redeeming Love, this is Michael Hosea’s main tactic for trying to get Angel to marry him, and later to stay with him. Especially interesting because he was not (at first) in love with Angel—he was trying to rescue her from her life as a Sex Slave, and often went to lengths of Honor Before Reason while invoking this trope.
Dave Malkoff from the Troubleshooters series, who pines after Sophia, who in turn pines after Decker, who won't sack up and ask her out. Eventually Dave wins.
Thrushpelt in the Warrior Cats novel Bluestar's Prophecy spends most of the book complimenting and helping Bluestar, but to his chagrin, she is not really interested in him like that. He remains her friend to the end.
Most of the protagonists' love interests in the Tortall Universe by Tamora Pierce are either dogged or outright pushy. The writing supports this attitude as okay except in a few cases where it becomes Entitled to Have You (as with Jon and Alanna).
Sam Haine the pumpkinhead from City of Devils, really thinks Nick would be a good pumpkinhead. He's mostly nice, but some of his behavior is a little questionable, and he seems not to be clear on "no."
In the short story Bombshells, Molly Carpenter reveals herself to be this. When Harry rejected her in Proven Guilty'' (for several reasons, including her young age) her response was essentially; 'Okay, I can wait.' Unlike most examples of the trope, she is shown to date other people.
A rare all-female example of the low-key yearning kind can be found in the Jacobs Ladder Trilogy. Rien loves Perceval, and she wants to go all-out with her, but Perceval is basically asexual and unwilling to, even though she comes to reciprocate Rien's feelings to some degree. Rien keeps trying, anyway, and it's not making either of them very happy.
Wesley, as creepily as the show can manage. When he's not being turned into a misogynist rage monster and attacking Fred, he's casually dropping death threats to Gunn, his romantic rival.
Doyle to Cordelia.
Family Matters' own Extraverted Nerd Steve Urkel who is treated like a fungus for most of the show's run but he eventually does end up winning Laura's heart.
Niles from Frasier, although he genuinely was too shy to tell Daphne, and she remained comically oblivious for most of the show's run.
Niles is also married a good portion of the time, and feels that his love and loyalty is owed to his wife, despite his feelings for Daphne.
Chase from House, for a while. That whole 'It's Tuesday and I like you' thing.
Harris Pemberton in Seriously Weird was trying to play this role to the obligatory Alpha Bitch. The one time he actually manages to convince her to go on a date with him, one of his friends (the female black New Age one) was almost blown to the other side of the planet. This is why you should not date the Weirdness Magnet.
Marcus is also this to Ivanova. However, his story arc ends in an Heroic Sacrifice, not a Face-Heel Turn. She's left devestated, regretting she never returned his advances and told him how she felt, and apparently spends the rest of her life recovering.
Noah's Arc: Interestingly enough, Ricky is this to Noah. Ricky shows increasing emotional investment and protectiveness of Noah, particularly after the gay bashing, but it's revealed in the movie that Ricky has actually been in love with him for some time.
Stiles from Teen Wolf, who crushes on Lydia, who really doesn't care.
Lydia flirts with Stiles in the fifth episode when he came by to see if she was okay - much to his delight, at least until he finds out that she's only doing so because she was really drugged up and thought he was Jackson.
By the end of the second season, Lydia is at the very least aware of Stiles' feelings for her, and does actually seem to care about him, but its unknown whether the attraction is even remotely reciprocated, considering her and Jackson's relationship.
By the middle of the third season, they have become close friends. Lydia even kisses him, to stop a panic attack he is having. And when Stiles has to undergo a sacrifice ritual, he is paired with Lydia because she is someone he has a strong bond with - "a sort of emotional tether." Wordof God is that Stiles and Lydia getting together is "the long game."
The TV Adaptation of 10 Things I Hate About You badly miscalculates this with the character of Cameron. While in the film he's a genuine Nice Guy, the tv version never actually tells Bianca he's interested in her (he tries once in French, which he knows she doesn't understand, and sends her a note he knows she never received). When she assumes he's gay, he makes only a cursory attempt to deny it. In one episode, she arranges to go to a dance with a Jerk Jock, and he sabotages the guy's car and steals his cell phone to make her think she has been stood up, then offers to go with her in his place. Given that he comes off like a creepy stalker, and she has a really sweet chemistry with Joey (who was a Jerk Jock in the film), the show seems to be writing itself into a corner.
Harper in Wizards of Waverly Place is a rare female version vis a vis Justin. They seemed to drop this when Harper moved in with the Russos in the third season, though, probably to prevent some questions about what they do together when no one's around...
Freddie in iCarly towards Carly. He flits between a mild case of a Played for Laughspuppy dog crush in season 1, this in season 2, and I Want My Beloved to Be Happy in season 3. Although he doesn't especially qualify for either major type of this trope: he doesn't sabotage her relationships, but he was also pretty clear about liking her, whilst not being over the top in trying to woo her. As they grew up, Freddie and Carly went from being next door buddies, to true best friends. The final episode of the show has Carly giving him a romantic kiss.
And now Freddie has a Spiritual Successor in A.N.T. Farm's Fletcher Quimby who serves just the same functions as Freddie did but minus the nerd tendency. And thankfully, no version of Sam to annoy him.
Both incarnations of the reality show Average Joe featured entire casts of Dogged Nice Guys — ugly and/or morbidly obese men vying for the affections of a stunning supermodel. At one point, the producers send a boatload of chiseled hunks to compete with the Joes, who instantly feel slighted by the new competition. This highlights the Double Standard and enormous sense of entitlement inherent in this trope, as the Joes begin lashing out at the supermodel for turning her attention to the hunks, calling her shallow...never mind that the Joes themselves only went on the show for the chance to get with a supermodel and that, at the end of the day, they are no kinder or more intelligent than the attractive men.
Cody of The Suite Life On Deck acted this way toward Bailey for most of the first season. This is a mild subversion, as it was pretty clear that she liked him, too. When they got together, the writers shifted this trait onto Marcus Little, toward London Tipton, who is too much in her own world to notice.
Ed played this straight. The titular character's behavior would have gotten him a restraining order within the first episode in real life.
Friends: Ross towards Rachel in Season 1. At the end of season 3 Chandler to Monica (his best friend of over five years), as he repeatedly insists they'd be a great couple. His true intentions are ambiguous but given they get together a season later, its unclear whether he was kidding around or actually had feelings for her.
In the first season of How I Met Your Mother, this kind of quest is the main story arc for Ted Mosby. The series finale shows him getting the initial target girl 25 years later. Talk about, uhh, persistence.
Subverted in season 3 with Stella, where Stella has just as big a crush on Ted as he does on her, but she's a single mother and a doctor with practically no free time and doesn't think she has any time for dating. His solution is priceless.
Xander has a crush on Buffy that's usually in the background but seen best in "The Pack." It eventually died on the show, though in the season 8 comics Buffy realizes she may have fallen for him. However, by then he's dating Buffy's sister Dawn.
Clem's in love with Harmony.
Theresa was a Dogged Nice Girl toward Ethan when Passions began its run. However, he eventually reciprocated her affections.
Detective Batista from Dexter eventually convinces Gianna that he is, actually, a nice guy, despite their... less than auspicious meeting. When she says she just wants to be friends, he says he'd be OK with that... and this is what finally wins her over.
The writers of The Big Bang Theory seem to be using this trope as an operating manual for Leonard in his relationship with Penny.
Seamus Harper is this toward Rommie in Andromeda. That's right, he's in love with a warship. Kind of goes with being a Gadgeteer Genius I guess.
A gay example is Justin in Queer as Folk. He stalks Brian quite perseverantly until he tolerates his company and eventually they achieve a normal relationship.
Tales of the Unexpected adapted a John Collier short story "Youth from Vienna" - a geeky scientist persistently courts a tv newscaster until she relents - but she dumps him for a tennis player, figuring him as a better fit. The scientist acquiesces, and gives them a wedding present - a prototype youth-retaining serum, warning them that it's a single dose, and splitting it would be fatal. It turns out to be merely flavored water, allowing the scientist to prove the couple really didn't care for each other, as they had each drank and refilled the vial behind the other's back. She gets back together with the scientist to a hinted-at happy ending.
Hubble on Bunheads is given to spectacular romantic displays. He succeeds, then dies at the end of the pilot.
Farscape has both positive and negative examples. John displays a low-key yearning for Aeryn for a long time before they finally start seriously dating (they have heavy UST and are even implied to have casual sex a couple of times during this period), and they're presented as the Official Couple. By contrast, Stark, after his lover Zhaan dies, acts this way toward Aeryn as well in a quite creepy way, hanging around her shyly and occasionally making ham-fisted attempts to hit on her. After John dies, Aeryn finally blows up at Stark in a memorably vicious "The Reason You Suck" Speech, telling him that Crais (another unwelcome suitor who Stark hates) is better than he is because Crais admits to himself that he wants to have sex with her and doesn't kid himself that he's "saving" her or deeply and unselfishly in love.
Kingsley from Fresh Meat is this to Josie, but this gets complicated when a) she already has a boyfriend; b) she sleeps with him as an apology; and c) he sleeps with someone else not long before that, leading to massive UST by the end of the first series. He returns wearing a trilby, sporting a soul patch and yo-yo, and puts on a dismissive attitude towards sex and women, making him look like a pick-up artist in training (it doesn't help he's later seen reading The Game). He and Josie do hook up eventually, but by then he's stopped being a complete tool.
Parodied on Inside Amy Schumer in a sketch called "Hello M'Lady" a commercial for an "app for your smart phone that lets you manage those clingy, fragile guys who think they're dating you".
Law & Order: SVU, naturally, featured a dark deconstruction of this trope in which a dogged nice guy committed a series of rapes in order to cause a neighborhood panic. The local panic gave him a pretext to bond with the object of his affections over their shared need to protect the neighborhood, when she otherwise barely noticed him and gave no hint of returning his feelings. Eventually he escalated to attacking her (and then pretending to save her!) when he found out she was seeing someone else.
"The arena is empty, except for one man Still driving and striving as fast as he can The sun has gone down and the moon has come up And long ago somebody left with the cup But he's driving and striving, and hugging the turns And thinking of someone for whom he still burns."
"You Belong With Me" by Taylor Swift. Except it's a Dogged Nice Girl this time.
"Teardrops On My Guitar" as well.
"Soft Rocked By Me" by Jonathan Coulton, who admitted it ended up seeming way creepier than he meant it to be.
* "Surrender" by Billy Talent.
* Gakupo in "Go Google It" by Luka Megurine and Gakupo Kamui.
Duncan Sheik's "Little Hands" ends with the protagonist accepting his fate... for now:
"Little hands, open smile I'm glad we got to talk for a while I feel OK, yeah, I'm feeling better I'll let her go, but I'll never say never..."
For Better or for Worse had Anthony, who combined the Patient Type with a passive-aggressive Entitled to Have You. After dating Elizabeth off-and-on and agreeing to be Just Friends, he spent the later years of the strip pining after her and broadcasting the fact he was still interested and willing to wait for her... despite getting married in the meantime. Readers were meant to accept that he was purely a Nice Guy and Liz's destined love, and that Therese was a horrible woman who had no right to be jealous of their relationship.
Deconstructed in FoxTrot when Paige spends some time worrying about Morton asking her to the dance like he always does, where she will have to turn him down, like she always does. Then she finds out that he asked someone else, and instantly gets upset that he didn't even try. When she finally brings herself to confront him, she says she's offended that he forgot about her, and he says he didn't ask because he remembered.
Paige: Morton, you're killing my ego. Morton: Egos heal.
Baldur's Gate II features the Violent Glaswegian dwarf fighter Korgan Bloodaxe, who will make advances towards a fellow tiny fighter, halfling Mazzy Fentan, should the player pick both for his party. The main reason Mazzy isn't very interested in him is that he, contrary to the trope name, is not a very nice guy at all.
"Hey, Mazzy! Just so's you know, I've somethin' long, hard, and low t'the ground you're free to touch and fondle if ye wish. No need to glare, girlie: I was talking aboot me axe!"
Similarly, when Athena Asamiya and Sie Kensou made the jump from Psycho Soldier to KOF, Kensou went from an Arrogant Kung-Fu Guy to Athena's Dogged Nice Guy who's hopelessly in love with Athena (who, otoh, is aware of his feelings but while she does care, she simply likes him just as a friend). Like in Mai's case, though, Kensou is a pretty decent person and friend outside this particular liaison; also, in the counted times when the usually self-reliant Athena has needed help from him, he has given it to her without expecting retribution. (He's dogged and all, but he does have his limits.)
Knights of the Old Republic. The male character's romance with Bastila consists mainly of immature teasing, but once you actually suggest a real relationship to her, she says no. If you want to achieve the romance, you pretty much have to keep pushing her and pushing her, regardless of how many times she turns you down. Though to be fair, she does make it quite obvious that she likes you too, and that it's only the Jedi code stopping her from saying yes.
Tekken had the sumo wrestler Ganryu, who at first fell madly in love with Michelle Chang, and later for her adopted daughter Julia. This one is actually a subversion, because towards Michelle, Ganryu can be seen as a Stalker with a Crush, since he was a corrupt sumo wrestler during the course of the early Tekken series (this disgusted Michelle)... but after he reappears in Tekken 5, he seems to have converted into a decent man and fits this trope towards Julia better.
There is also Kuma, Heihachi's pet bear, who is this to Panda, Xiaoyu's companion. He's general nice when the mood suits him, and tries his hardest to get Panda to like him. Sadly, Panda hates him with a passion and clams to be too old for him (which is odd since the age difference is by a year, even in bear standards).
Eruru from Utawarerumono toward Hakuoro, not because he's trying to avoid anything, but because he can't get a clue. He's a Chaste Hero, but in the oblivious sense, not the nonsexual sense, obviously. He has a vague idea that his relationships with other girls might make Eruru jealous - but doesn't really think about why she would be - at one or two points.
In Super Robot Wars 64, this is Reese Gresewell's curse. He originally worked for OZ, but fell hard for heroine Selain Meneth, who just so happened to be his enemy and the one he was ordered to hunt down because she ganked the twin to his Ace Custom mech. Unfortunately, by the time he does a Heel-Face Turn, she has no desire to be with him romantically.
Reconstructed in Guild Wars. Gwen spends all of her time angsting alone, and Keiran spends all of his trying to cheer her up. He succeeds in making Gwen fall for him, but she refuses to give in to her feelings because angsting about her past is more important to her. Eventually, Keiran's efforts go too far and Gwen openly rejects him. Heartbroken by her harsh words, he decides she's a lost cause, runs off to war, and goes missing for several weeks. During this separation, they both realise that they've been acting like childish fools, and when Keiran comes home (or rather, when Gwen figures out where he is and rushes out into the wilderness to save him), he simply asks her to marry him. She says yes.
Mass Effect: Poor Dr. Michel. She has a massive crush on Garrus (since he helped rescue her near the beginning of the first game). And he has no idea. In the second game, she sends an email to Shepard asking whether (s)he's seen him and if he's alright, and bringing Garrus to the geth dreadnought mission in the third game leads to this conversation:
Garrus: Dr. Michel did get me some dextro-amino chocolate. You're welcome to it, once we're back. Tali: She got you turian chocolate? Garrus: She said she saw it and thought of me...why? Tali: (innocently) Oh, nothing. / (if Shepard romanced Garrus) Watch yourself, Shepard.
Sakura Kasugano from the Street Fighter series may be one for main character Ryu. She not only still really wants Ryu to train her personally, despite him telling her he could not train her as he still had much to learn himself, it is heavily implied that her admiration towards Ryu has developed into full on romantic feelings by the time of The Ties that Bind and SFIV — specially when she Cool down hugs him back to sanity when he almost loses himself to the Satsui no Hado in the first. Yet since fighting is—literally—everything for Ryu, it's obvious that while he cares for Sakura greatly, he's not really the type to consider things like romance in the first place. (Which he even admits to Crimson Viper in IV). The age difference, which is pretty notorious in IV as Ryu has visibly aged while Sakura still looks like a teenager despite being 19, doesn't help.
(When winning against Sagat) "I totally understand your obsession with Ryu. Isn't he just dreamy?"
The Monkey Island series has Guybrush and Elaine's turbulent relationship. The Secret Of Monkey Island has the main character Guybrush in love with Elaine even though she thinks he's pathetic. She initially showed him contempt, before later finally realising she does like him, only for LeChuck to kidnap her later on, after which she isn't interested in Guybrush anymore. By Monkey Island 2: LeChuck's Revenge, she has moved to get away from him and has named her dog after Guybrush as a sign of what she thinks of him. Guybrush initially succeeds at winning her back, until she realises that the only thing he wants is her map piece. By The Curse of Monkey Island, they have gotten engaged, but he accidentally gives her a cursed diamond ring which turns her into a statue - the game is about turning her back to normal. By Escape from Monkey Island they have gotten married and have moved back to her mansion on Melee Island to live together. By this point she exerts control over him and because he likes her so much he is scared not to go along with it.
Cordelia: "Is this another of your schemes to make me feel better?"
Henry: "Nya ha! No, it's a scheme to make you fall in love with me. (...) I'm just gonna work hard so you end up liking me instead!"
Oddly enough for someone so normally popular, Tomoya in CLANNAD becomes one of these in regards to Misae. However, it's not so much that she's actually uninterested as that she decided she wouldn't get involved with anyone except her first love, and is currently still waiting for him. Except that he turned into a cat and never left her. Long story. She more or less gets worn down into admitting she does like him.
In Grisaia No Kajitsu Amane confesses early on in the common route and keeps pursuing him, but Yuuji is suspicious because it just seems too convenient for a tall, beautiful, friendly and domestic woman to "fall for him at first sight" and turns her down. His suspicions were pretty much spot on, too, because she asks to be his girlfriend as a coping mechanism and not because she loves him. At first. In Grisaia No Meikyuu we get two more with Millie and Chiara, though Yuuji just finds the former annoying and tunes out the latter.
Dave is a deconstruction. His obsession with Margaret varies between mildly creepy to just plain sad, with him pretty much ignoring all other chances at happiness to focus exclusively on her. It doesn't help that Margaret is a tsundere who is genuinely in love with him, but only platonically. And she slept with him to save his life, but failed to explain that detail to him until after. Eventually, they have a long talk where he acknowledges his obsession, they share a tender kiss goodbye, and he leaves for Blue.
Blue, on the other hand, is played surprisingly straight. When she comes to visit her brother Mike, she immediately falls for his roommate Dave. Although she has some fun playfully stalking him for a few days, she mostly just remains quietly supportive, even when Dave yells at her for things like being nice to his parents (in his mind, Margaret was the one his parents were supposed to adore). She even sleeps with him after he suffers some serious mental trauma, but is still willing to step back and let him work things out at his own pace rather than forcing the issue. Eventually, they officially get together for good. Though the fact that Dave gave her father a heart attack that killed him does put a damper on their relationship for a while.
ThisXKCD comic is a ruthless deconstruction showing exactly how creepy this can be. Though it may seem like the guy in the strip Cannot Spit It Out, he actually deliberately doesn't talk to the girl about how he wants to date her because he's too scared by the possibility that she could reject him, so he decides not to "force the issue". He instead integrates himself into her life, until she feels dependent on him and succumbs before her feelings. It caused quite the Internet Backdraft on the xkcd forums. A certain contingent saw nothing wrong with the guy's actions.
And another presents amplexus, where the male simply holds on long enough for the female to agree to mate.
Piro in MegaTokyo is a subversion. He appears to be this by most traditional traits, but in truth, his inability to get a girlfriend is mostly self-inflicted by a total lack of confidence. In a more traditional sense, Kimiko was something of a Dogged Nice Girl to Piro.
Angus after Faye in Questionable Content. He follows her to the point of being asked to leave and THROWN across a bar by Faye. Against all odds, they seem to be flirting despite the creepy beginning. Given Faye's personality and her issues, this is pretty much the only approach that may have had a chance of working and getting her to actually date him.
Mike in Bittersweet Candy Bowl spends a lot of time being this to Lucy, although he tries to be subtle about it. Subverted; he finally gives up, and falls (back) in love with a different childhood sweetheart.
Deconstructed inShadowgirls, where Jackson decides to stand up for himself instead of just being Charon's best friend, on the advice of the "jerk" Charon is seeing, named Gage, who keeps trying to manipulate her into sex. Note that when he does tell her, she reveals that she knew already, and uses the same manipulative techniques Gage used earliernote Attempting to put the blame on the target for not wanting to do what the manipulator wants, and using "if you really loved me" ultimatums. The jerk wanted sex from Charon, and Charon wanted emotional intimacy from Jack. The Dramatic Irony is, we know that Jackson ends up falling in love with, getting married to and having a child with Alpha Bitch Chrissy, even though he still loves Charon to some extent, and Charon becomes the town bicycle.
Homestuck: Cronus, as a parody of the way the fandom tends to see Eridan, is a Jerkass exaggeration of this trope. While he claims to be a kind, sensitive soul, the fact that he only ever does anything nice in the hopes that the other person will sleep with him (and when that offer's off the table becomes downright abusive) and absolutely refuses to take no for an answer makes him so much of an asshole that he's the only one in his group that absolutely no-one else can stand.
Matt the otter from Hodges Pond is this towards Trixie the ferret.
Ken in Shortpacked! is introduced head-over-heels in love with his roommate Malaya, but seems to think just standing around being supportive will win her over. Malaya doesn't notice, or more likely, doesn't care.
Arnold: Don't worry, Ken. She'll come around. Ken: Really? Arnold: No, you're an idiot. Stop barking up the bitch tree.
Fortunately (for both of them), he seems to have eventually figured it out and gotten over her. They get along better as not-that-close friends ever since.
Lampshaded and Discussed with Jako and his crush Jordie in Our Little Adventure. Though Jako is good aligned, he's not subtle and given to spectacular romantic displays. Since Jordie's also good aligned, he really doesn't want to hurt Jako's feelings by rejecting him. It doesn't help that all the human members of the adventuring group except Rocky seem to be a Shipper on Deck with the two boys.
Stalwart from Whateley Academy. He's first seen declaring his true love for protagonist Fey, who then uses her powers to magically throw him across the campus quad. But Stalwart is a nice guy and keeps trying, almost to the point of becoming a Stalker with a Crush. His persistence is rewarded when he becomes the only thing that stops a superpowered ninja from raping and killing Fey... and he almost dies from doing so. Fey heals him and ends up going on a date with him.
Dr. Horrible's Sing-Along Blog is about an Ineffectual Sympathetic Villain who has a crush on a girl he sees at a coin laundry but can't muster the courage to talk to. Instead, he finds himself shunted aside by his archrival Captain Hammer in the bid for her affections, and engages in increasingly stalker-like behavior as a result, culminating in a Murder the Hypotenuse plot that Goes Horribly Wrong. Though it's arguably subverted in that it's heavily implied Penny thought Billy was attractive and likable and probably would have willingly gone out with him instead had he ever stopped admiring her from afar and actually talked to her; he just took so long that Hammer beat him to it.
The The Art Of Manliness is a website that critisizes the Dogged Nice Guy in a number of podcasts and articles, not because he's nice, but because he's often not nearly as nice as he thinks. He's often passive aggressive and too insecure with himself to be honest with how he feels.
The most famous and deliberately over-the-top example is probably cartoon character Pepe Le Pew, whose main problem is not understanding that, as a skunk, he smells bad (when he did in 1959's "Really Scent," he corrected the problem, only to have the cat go to a Limburger factory to make herself smell bad). Chuck Jones (the director who created Pepe) based Pepe Le Pew on fellow Termite Terrace writer, Ted Pierce, who was notorious for hitting on women and often forgetting to shower after a night of partying (though the fact that Pepe is a skunk from France carries Unfortunate Implications about how Europeans [particularly the French] aren't as hung up on hygiene as Americans are). Add the fact that Pepe is just so friggin' relentless when it comes to wooing female cats (or any animal with a skunk stripe) and you can see why the Pepe cartoons get a lot of sexual harassment/rape accusations from Media Watchdogs. This is likely the main reason his Tiny Toon Adventures counterpart is female.
Fry from Futurama chased comically after Leela. As time went on Leela returned more and more of his affection.
"I've been a fool! A fully-justified, prudent fool!"
Milhouse Van Houten of the The Simpsons definitely counts. He's flirted with Lisa too many times to count and even openly declared his love for her a few times, only for her to shut him down almost every time. Doesn't stop him from trying again...and again...and yet again....
Silverbolt in Beast Wars. It helps that he's part dog (well, wolf, but Rattrap calls him "bird-dog").
Both Kyle and Token in the South Park episode "Cartman Finds Love".
Martin in W.I.T.C.H., constantly shot down in his pursuit of Irma.
Sheldon functions as this towards Jenny in My Life as a Teenage Robot. In-series, Jenny never returns his affections, but according to Word of God, Sheldon would have eventually ended up with Jenny if the series hadn't been cancelled.
Bolin in The Legend of Korra. Despite being supportive of and nice to Korra from the moment he meets her, she settles for his brother Mako, who becomes more cordial with her after he learns that she is the Avatar.
Mordecai of Regular Show started off as this to Margaret, who seemed to have new boyfriends every time she met him, until it was deconstructed to nothing in season 3.
Braco from Adventure Time is like this towards PB, despite her constant detests. He ends up digging his own grave with his actions, eventually making a Deal with the Devil and becoming a Humanoid Abomination. PB ends up creating a robot lookalike for him, which at first he is uncomfortable with, but the moment it shows physical attraction toward him, he has a change of heart.
Gideon from Gravity Falls is a deconstruction of this trope. He is devoted to Mabel but she just wants to be friends, and in-universe everyone seems to think that his attempts to win her over are charming...but the truth is, Gideon is an Ax-Crazy, Entitled Bastard who uses emotional manipulation to trap Mabel into a relationship. He performs over-the-top acts of kindness, manipulates her into going into more dates with him by asking her very publicly in front of large crowds of Gravity Falls citizens who think it's just so adorable that Gideon might finally get a girlfriend, and completely ignores her wish to not be in a relationship with him. Eventually, Dipper tries to break the news that Mabel is not interested in Gideon to him, and Gideon responds to this by attempting to murder Dipper because he believes that Dipper got in between him and Mabel. Thankfully, Mabel sees this and intervenes, and she rejects him, not only romantically, but as a friend now, too.
Mabel:(after rejecting Gideon again) But we can still be makeover buddies, right? Wouldn't you like that?
Mabel:(rips amulet away from Gideon) No, not really! You are like attacking my brother, what the heck!