History Main / TheFirstCutisTheDeepest

* At the beginning of ''Manga/KodomoNoOmocha'', child star Sana claims to be in a romantic relationship with her older manager Rei, whom she refers to as her "gigolo". After she is made to understand what's wrong with this ''and'' it looks like he may get back with his old girlfriend Asako Kurumi, she's left confused about romance, and this is one of the factors that impedes her getting together with Hayama.

** [[spoiler:Dumbledore]] had this as part of his backstory. Though it never directly came up in the books, Creator/JKRowling revealed all the details to the public. [[spoiler:The man who broke his heart was none other than Gellert Grindelwald, a [[FantasticRacism Fantastic Racist]] who went on to become first Wizard Hitler of the 20th century. For a while, Dumbledore was so deeply in love that he espoused Grindelwald's views and was more than willing to work to establish wizard supremacy over Muggles. After his sister's death, though, Grindelwald fled the country and Dumbledore thereafter led a celibate life and never got involved with anyone else again for fear that allowing himself to love another man would [[LoveMakesYouEvil cause him to again completely lose his moral compass]].]]

* ''Literature/{{Semiosis}}'': The sapient bamboo-like PlantAlien Stevland had formed a symbiosis with the Glassmaker aliens, who then disappeared and abandoned him to starve. This leaves Stevland slow to trust the human colonists who come to the planet; when the Glassmakers are rediscovered, Stevland is initially opposed to opening any contact with them.

** Also occurs, surprisingly enough, with Casey. He still carries a great deal of grief over the [[spoiler: apparent death during a bombing of his AP photographer girlfriend in Chechnya, who later turned out to have survived and was actually a French spy]]. However much more significant was the even earlier loss of [[spoiler: his fiance, Kathleen McHugh, who he was forced to give up when he faked his death to join a Marine Special Forces unit]]. How profoundly the latter affected him can be seen when, after a mission to protect [[spoiler: Kathleen and the daughter he didn't realize he had from his ex-commanding officer]] forced him to confront what he had lost, for the first time in the series Casey openly warned Chuck about letting Sarah slip away, and openly showed support for his feelings for her.

* ''LightNovel/HighSchoolDxD'' has the protagonist Issei Hyoudou is unable to even think that the girls in his harem love him at all despite his own claimed goal to be a harem king and them doing all sorts of intimate things in front of him, short of actual sex, because he already hit the DespairEventHorizon after his last relationship failed. He was ''murdered'' by his first girlfriend Raynare(which was the catalyst for his resurrection as a devil) because said girlfriend turned out to be a sadistic FallenAngel who wanted his Sacred Gear but ultimately decided it wasn't worth it and killed him after their date. Notably when he does manage to heal from this wound to his heart the amount of official relationships he has ''skyrockets'' after this (and [[spoiler: that time he died and came back, but that's a different trope]]).

* While it's not the first cut, Ted from Series/HowIMetYourMother has to eventually admit that being left at the altar gave him some serious emotional baggage to deal with.

* If someone works up the courage to ask someone for the very first time (usually in high school) and they get rejected, it is not at all unusual for it to be ''years'' before they manage to ask anyone out again, the rejection hurts ''that'' bad. One counselor told a story of a man (good looking, physically fit, and successful) who'd come to her out of sheer desperation, terrified that he was going to spend the rest of his life alone because he just couldn't work up the nerve to ask a woman out. The counselor found out it all stemmed from when he was sixteen years old, asked a girl out and got rejected. The man's age when he finally came to her? ''Twenty-nine.''

* ''Disney/{{Hercules}}'' - Megara's first boyfriend, an UngratefulBastard who dumped her ''after'' she sold her soul to Hades to save him, ''really'' soured her on men.

* In ''Disney/WreckItRalph'', Sergeant Calhoun had the most Tragic BackStory ever -- her beloved boyfriend died ''at the altar and during their wedding'' because [[MyGreatestFailure she forgot to do a perimeter check for escaped Cy-Bugs.]] [[spoiler:Really painful when Felix, moving into SecondLove, uses the same line that he used all the time (without knowing the story behind it, to be fair) and poor Calhoun has a huge HeroicBSOD.]]

*** her first crush Higashi happened also to be Narkissos, ''the first youma she ever killed'' (and ''after'' learning his real identity to boot). What followed was a string of crushes that Artemis sarcastically called "Minako's 5,000 First Loves" (because Minako called one of those crushes her first love and because, including Higashi, [[ExactlyWhatItSaysOnTheTin they were exactly 5,000]]);
*** number 5,000 of Minako's crushes, Ace, was also her true love. After, [[DoomedByCanon as expected, he died in the final chapter]] [[spoiler: because she found out he was Kunzite's subordinate and killed him]], Minako ''swore off men'' because [[MarriedToTheJob they were in the way of her duty]] (Minako's possible love with [[LesYay Rei]] doesn't count because she's a girl and it doesn't get in the way of duty).

* Also, for those tropers who had a recent break up with your first boyfriend/girlfriend, it's something [[TruthInTelevision perfectly normal]], [[EarnYourHappyEnding you'll]] [[SecondLove find another one]]. [[YouAreNotAlone Believe it.]]

* ''LightNovel/HighSchoolDxD'' has the protagonist Issei Hyoudou is unable to even think that the girls in his harem love him at all despite his own claimed goal to be a harem king and them doing all sorts of intimate things in front of him, short of actual sex, because he already hit the DespairEventHorizon after his last relationship failed. He was ''murdered'' by his first girlfriend Raynare(which was the catalyst for his resurrection as a devil) because said girlfriend turned out to be a sadistic FallenAngel who wanted his Sacred Gear but ultimately decided it wasn't worth it and killed him after their date. Notably when he does manage to heal from this wound to his heart the amount of official relationships he has ''skyrockets'' after this (and [spoiler: that time he died and came back, but that's a different trope]]).

* ''LightNovel/HighSchoolDxD'' has the protagonist Issei Hyoudou is unable to even think that the girls in his harem love him at all despite his own claimed goal to be a harem king and them doing all sorts of intimate things in front of him, short of actual sex, because he already hit the DespairEventHorizon after his last relationship failed. He was ''murdered'' by his first girlfriend Raynare(which was the catalyst for his resurrection as a devil) because said girlfriend turned out to be a sadistic FallenAngel who wanted his Sacred Gear but ultimately decided it wasn't worth it and killed him after their date. Notably when he does manage to heal from this wound the amount of official relationships he has ''skyrockets''.

* ''LightNovel/HighSchoolDxD'' has the protagonist Issei Hyoudou is unable to even think that the girls in his harem love him at all despite his own claimed goal to be a harem king and them doing all sorts of intimate things in front of him, short of actual sex, because he already hit the DespairEventHorizon after his last relationship failed. He was ''murdered'' by his first girlfriend (which was the catalyst for his resurrection as a devil) because said girlfriend turned out to be a sadistic FallenAngel who wanted his Sacred Gear but ultimately decided it wasn't worth it and killed him after their date.

** Rei had fallen in love with her father's secretary, but he married another woman. This version of Rei would later declare she had swore off men, partly because of this and partly [[MarriedToTheJob because they were in the way of her duty as a Sailor Senshi]];

* Discussed in ''Manga/Evangelion303'': In chapter 13 Asuka tries--and fails--to convince Shinji to break up arguing that he is attached to her because she is the first woman that he has ever been with, and men often become attached to their first sexual relationship.
* ''Fanfic/{{HERZ}}'': Natsume thinks that her sister Kurumi is so fixated on Shinji because he was her first love and she simply can not let it go despite of him being married to someone else.

** After the last battle, [[spoiler:Misato and Makoto started dating.]] However Shinji thinks [[spoiler:his guardian]] can not completely love [[spoiler:Makoto]] because she never stopped loving her first lover.

* Gwen from the ''WesternAnimation/{{Ben 10}}'' fanfic series ''[[http://www.fanfiction.net/s/3875254/1/Hero-High-Earth-style Hero High]]'' went out with the most popular guy in her school before the start of the series, where it turned out that "dating her for three days" was the cost of a bet he and his friends did. Naturally Gwen is skeptical pretty much every step when a handsome and extremely rich guy shows interest in her.

* In ''FanFic/BrideOfDiscord'', Discord, who is heavily implied to have had feelings for Princess Celestia, reveals that Celestia rejecting him after he misunderstood what she meant by "help the ponies" was one of the main catalyst for him deciding to turn Equestria into a WorldGoneMad.

* ''Film/JustLikeHeaven'' had the grief variant with David's wife's death keeping him from forming any new relationships. Elizabeth ''thinks'' it's the first variety at first, and mocks him over his inability to get over being dumped.

* A variation on this trope is seen in ''Film/TheUglyTruth''. Abby suspects that the reason Mike is so cynical when it comes to women and relationships is because a woman broke his heart once. But it turns out that he had been mistreated in ''every'' relationship he'd ever been in. By the time he turned 30 years old, he firmly believed that there was no such thing as a good relationship.

* Arya in the ''Literature/InheritanceCycle'' has significant baggage related to her friend/possible lover Faolin, who was killed by Durza and his Urgal thralls at the beginning of the first book. This seriously impairs any possible relationship with Eragon, and is part of why she rejects him.
* In ''[[Literature/HeraldsOfValdemar The Last Herald-Mage]]'' Herald Vanyel never gets over the suicide of his first love, Tylendel. When he finally loves again, his beloved Stefen turns out to be 'Lendel reincarnated, though neither of them realize it at first.

* In ''Literature/{{Persuasion}}'', Captain Wentworth can't get over an old heartbreak, but it complicates his relationship with the ''same woman''. After Anne Elliot broke their engagement, he spent eight years at sea in the Napoleonic Wars and winds up in her social circle by accident. His sister and brother-in-law are sure he's looking for a wife because he makes a lot of noise about wanting a woman of firm character and flirts with the Musgrove sisters, but in truth he's being passive-aggressive at Anne--he's still in love with her. (Fortunately for them both, she still loves him, and he gets over himself enough to rectify things.)

* ''Series/{{Chuck}}'' had this with Chuck and his ex Jill, and Sarah's ex partner (in both the cop way and the sleeping together way) with Bryce Larkin.

** [[spoiler: Surprisingly the case for the mother as well. Her first love, Max, died on her 21st birthday and she spend most of the next eight years in mourning, never really moving on until she meets Ted.]]

** Ross: Carol, his first wife (and only woman he'd ever had sex with) left him for another woman, causing serious insecurity and jealousy issues for the rest of the show. His sister Monica even comments that Carol did a real number on him, as he was ''too'' trusting of his previous girlfriends.
** Chandler: Both [[{{FirstLove}} Janice]] and [[{{SecondLove}} Kathy]] did a lot of damage. While he already had CommitmentIssues, he'd got through them with Janice, thought Kathy was "The One" and was quick to admit he loved them. Thanks to them both cheating on him, he became even more insecure and commitment phobic. When he fell in love with his best friend Monica, he was clearly terrified, taking half a year to say he loved her and reveal their SecretRelationship. Even when they were married, he was an InsecureLoveInterest and worried she'd leave or cheat on him, despite her being the most reliable of the friends gang and obviously crazy about him.

* On ''Series/The100'', Clarke briefly returns Lexa's kiss, but says she's not ready to be involved with anyone yet, since her last romantic partner [[spoiler:died at her hands not too long ago]].
* On ''Series/ChoujinSentaiJetman'', Ryu was so broken up over losing Rie, that he kept burying himself in his work as a Jetman, ignoring Kaori's advances, when Rie was revealed to be brainwashed into becoming Maria, it got way worse.

** Another reason she resists becoming attached to anybody is because she broke the heart of one of her former lovers when she left him. She still feels guilty about it.

* In the ''VideoGame/FireEmblemGaiden'' remake, ''VideoGame/FireEmblemEchoesShadowsOfValentia'', some characters will play this straight if their prospect love interest kicks it in Classic Mode: [[spoiler: Mae (if Boey dies), Boey (if Mae dies), Gray (if Tobin lives but Clair dies), Clair (if Gray dies), [[CampGay Leon]] (if Valbar dies)]].[[note]](Tatiana subverts it: she plays it straight in the original, but in the remake she eventually has a SecondLove.)[[/note]]

** Erika's past with Hitoshi made her the BrokenBird she is today, and caused serious problems when she and Largo began to strike up a relationship.

* In ''Series/{{Dexter}}'' Dexter and Rita's relationship is slowed by her BrokenBird status due to her [[DomesticAbuser ex-husband]]. Unusually for this trope, Dexter chose to date her because of this as it left her, like him, uninterested in sex.

* {{Series/Merlin}} starts his series as a teenage boy who has a MeetCute with every single girl he meets, although due to one thing or another he never pursues it much farther. Until Freya came along, and he did, and she fell in love with him too. [[spoiler: It ended with her bleeding to death in his arms.]] Ever since that, he's been utterly uninterested in women, and WordOfGod confirms he's mostly [[{{Asexual}} asexual]] now.

* ''FanFic/{{Sehnsucht}}'': [[spoiler:The only person Cervello Cynthia ever (romantically) loved was Daemon Spade, who was in love with her adoptive sister. Cynthia, out of respect for their relationship, never confessed her feelings, though it's implied that Daemon was aware of them and, to some extent, returned them. [[CynicismCatalyst Then Elena died]]. Daemon ''never'' got over it, and subsquently followed through with his canon betrayal, and in spite of everything, Cynthia loved him too much to punish him for it. The memories of this tragic relationship still haunt her reincarnation Reiki Noriko, which was only compounded by Mukuro's similarities to Daemon and Daemon's own appearance. As a result, she's shown little to no interest in romance in her second life]].

* ''LightNovel/HighSchoolDxD'' has the protagonist Issei Hyoudou is unable to even think that the girls in his harem love him at all despite them doing all sorts of intimate things in front of him, short of actual sex, because he already hit the DespairEventHorizon after his last relationship failed. He was ''murdered by his first girlfriend'' because said girlfriend turned out to be ''a sadistic and insane Fallen Angel who wanted his Sacred Gear''.

* In ''Literature/{{Rebecca}}'', the female protagonist believes that her husband Maxim is still carrying a torch for the titular Rebecca, his exalted dead first wife. [[spoiler:Subverted when she learns that the beloved Rebecca was actually a Manipulative Bitch whom Maxim ''hated''.]]

* ''LightNovel/HighSchoolDxD'' has the protagonist Issei unable to even think that the girls in his harem love him at all despite them doing all sorts of intimate things in front of him, short of actual sex, because he still has the scars from his ex-girlfriend. Specifically, he was ''stabbed to death by his first girlfriend'' because said girlfriend was ''a sadistic and insane cult leader looking for artifacts in his stomach''. AND she murdered her little sister ''for a pair of earrings''!

* In ''FanFic/BrideOfDiscord'', Discord, who is heavily implied to have had feelings for Princess Celestia, reveals that Celestia rejecting him was after he misunderstood what she meant by "help the ponies" was the catalyst for his take over of Equestria.

* ''TalesOfTheAbyss'': You'd think that being smothered by a harem of busty ladies when he was five would turn [[spoiler:Guy Cecil]] into a perverted groper. Unfortunately, that's not as sexy as it sounds when all the women are DEAD from being used as meatshields and the recipient of all these stiffening boobs is currently suffocating to death underneath two hundred pounds of rotting flesh. And that is why [[spoiler:Guy Cecil]] cannot touch women without having a panic attack.

* In ''Literature/{{Rebecca}}'', the female protagonist believes that her husband Maxim is still carrying a torch for the titular Rebecca, his exalted dead first wife. [[spoiler:Subverted when she learns that the beloved Rebecca was actually a Manipulative Bitch who Maxim ''hated''.]]

* In ''{{Rebecca}}'', the female protagonist believes that her husband Maxim is still carrying a torch for the titular Rebecca, his exalted dead first wife. [[spoiler:Subverted when she learns that the beloved Rebecca was actually a Manipulative Bitch who Maxim ''hated''.]]

* Isabela's romance backstory in VideoGame/DragonAgeII gives this as the reason she is so casual about sex and resistant to any emotional attachment - her mother sold her into a loveless marriage. "She didn't even haggle over the price. Bitch."