History Main / TheFirstCutIsTheDeepest

* ''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, [[ParalyzingFearOfSexuality 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 number of official relationships he has ''skyrockets'' after this (and [[spoiler: that time he died and came back, but that's a different trope]]).

* Rudeus of ''LightNovel/MushokuTenseiJoblessReincarnation'' is devastated when [[spoiler:Eris]] [[NotStayingForBreakfast disappears after their first night together]], leaving a vaguely-worded note. Thinking he was somehow inadequate, for several years he's [[TheLoinsSleepTonight unable to feel aroused]] and it interferes with his next relationship.

* {{Implied|Trope}} in ''WesternAnimation/TheOwlHouse''. It's hinted that Luz Noceda has been turned down by multiple crushes in the past for being "cheesy", which is part of the reason why she's so hesitant to confess to [[spoiler:Amity]] without a GrandRomanticGesture.

* {{Implied|Trope}} in ''WesternAnimation/TheOwlHouse''. It's hinted that [[Characters/TheOwlHouseLuzNoceda Luz Noceda]] has been turned down by multiple crushes in the past for being "cheesy", which is part of the reason why she's so hesitant to confess to [[spoiler: [[Characters/TheOwlHouseAmityBlight Amity Blight]]]] without a GrandRomanticGesture.

* The {{Trope Namer|s}} is the song by Cat Stevens, [[CoveredUp which has been covered]] by P.P. Arnold, Keith Hampshire, Music/RodStewart, and Music/SherylCrow, describing just this kind of situation.

* ''[[https://archiveofourown.org/works/14878527/chapters/34453056 Second Chances]]'': Adrien and Marinette have both been widowed, but whereas it's been several years for him, and his marriage was already breaking down at the time, and he's been focused on raising his young daughter, for Marinette it's been less than a year and he was the love of her life, lost in a tragic accident. As a result, while Adrien and Marinette are both attracted to each other, they have to go slow, because even feeling like they're on a date can be enough to make Marinette break down in tears, both feeling her husband's loss, and feeling guilty for moving on.

* Implied in ''WesternAnimation/TheOwlHouse''. It's hinted that Luz has been turned down by multiple crushes in the past for being "cheesy", which is part of the reason why she's so hesitant to confess to [[spoiler:Amity]] without a GrandRomanticGesture.
* Implied in ''WesternAnimation/TotalDramaPresentsTheRidonculousRace''. Emma is nervous about getting into a relationship with Noah because of a bad break-up with her ex Jake, which was three years prior. While's it's never stated whether or not it was her first love or not, the trope still applies.

* In ''WesternAnimation/{{Gargoyles}}'', Goliath was in love with Demona and had a child with her but Demona would betray him and become a FallenHero, hurting Goliath deeply that his "Angel of the Night" would now hate him so much and go against everything the gargoyles believe in. This was partly the reason why it took Goliath a long time to realize his feelings for [[SecondLove Elisa]] (aside from the fact [[InterspeciesRomance they are of different species]]) and ironically he might not have ever realized he could have a chance with Elisa if it weren't for Demona and Puck's meddling.

* This shows up in ''Fanfic/AndTheStoryContinues''. Interestingly, L and Erin [[UnresolvedSexualTension didn't have an actual intimate relationship]] [[Fanfic/StoryOfTheCentury in the first story]], but the emotional baggage is still there now that Erin's developing a romantic interest in Stephen. It's probably why she decided this time around to ask him up front how much he liked her.

* Rudeus of ''LightNovel/MushokuTensei'' is devastated when [[spoiler:Eris]] [[NotStayingForBreakfast disappears after their first night together]], leaving a vaguely-worded note. Thinking he was somehow inadequate, for several years he's [[TheLoinsSleepTonight unable to feel aroused]] and it interferes with his next relationship.

* {{Series/Merlin|2008}} 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.

* In ''WesternAnimation/IceAge2TheMeltdown'', this pops up when Manny admits that he is finding it hard to love Ellie because of his loyalty to and memories of his FirstLove.

* ''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 number of official relationships he has ''skyrockets'' after this (and [[spoiler: that time he died and came back, but that's a different trope]]).

* In ''WesternAnimation/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.]]

* ''Manga/TheWallflower'': Sunako being cruelly rejected by her first love was what caused her to retreat to the darkness in the first place and is still one of the issues (though certainly not the only one) keeping her and Kyohei an AnchoredShip.

* ''Manga/GEGoodEnding'' has the main female character [[BrokenBird Kurokawa]] repeatedly plagued by the shadow of her ex-boyfriend, which keeps on haunting her even after she successfully gets together with Utsumi.
* ''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 number of official relationships he has ''skyrockets'' after this (and [[spoiler: that time he died and came back, but that's a different trope]]).
* A bad breakup with his first girlfriend [[spoiler:Athena]] as well as the ideas she drilled into his head have made Hayate in ''Manga/HayateTheCombatButler'' highly reluctant to even consider the idea of dating anyone in the foreseeable future. [[spoiler:While he does eventually work through this, he still ends the series single. At least so far as the reader can tell, anyway.]]

* The manga version of ''Manga/SailorMoon'' provides a few examples:
** Rei had fallen in love with her father's secretary, but he married another woman. This version of Rei would later declare she had sworn off men, partly because of this and partly [[MarriedToTheJob because they were in the way of her duty as a Sailor Senshi]];
** Unbelievably enough, Minako managed to get hit from this ''twice'' during the run of ''Manga/CodenameSailorV'':
*** 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 the most painful of her infatuations. 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).

* Rudeus of ''LightNovel/MushokuTensei'' is devastated when [[spoiler:Eris]] [[NotStayingForBreakfast disappears after their first night together]], leaving a vaguely-worded note. Thinking he was somehow inadequate, for several years he's [[TheLoinsSleepTonight unable to feel aroused]] and it interferes with his next relationship.

* ''Fanfic/HuntingTheUnicorn'', being a DeconstructionFic of the ButNotTooGay portrayal of [[Series/{{Glee}} Kurt and Blaine]], uses this to [[TearJerker heartbreaking]] effect; Blaine lost his virginity at 16, when he believed [[spoiler: and tried to ''invoke'']] SexEqualsLove. He ended up getting strung along for weeks by a guy who ''didn't'' and had no intention of taking responsibility, leaving him terrified of either getting hurt again or accidentally doing the same thing to Kurt.
* Gwen from the ''WesternAnimation/Ben10'' 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.
* This shows up in ''Fanfic/AndTheStoryContinues''. Interestingly, L and Erin [[UnresolvedSexualTension didn't have an actual intimate relationship]] [[Fanfic/StoryOfTheCentury in the first story]], but the emotional baggage is still there now that Erin's developing a romantic interest in Stephen. It's probably why she decided this time around to ask him up front how much he liked her.

* ''Fanfic/OldWest'': [[DeterminedHomesteader Grace Glossy]] hasn't dated anyone for ten years because her first love and husband Benjamin Hares suddenly abandoned her, pregnant and without a single penny. Once she realizes that she has fallen in love with [[JerkWithAHeartOfGold Rattlesnake Jake]], she's hesitant to reciprocate out of the fear of history repeating itself.
* 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 catalysts for him deciding to turn Equestria into a WorldGoneMad.

* In the 2008 film ''Film/GetSmart'', Agent 99 had this due to her bad breakup with [[spoiler: Agent 23]].

* In ''Film/ForgettingSarahMarshall'', Peter spends the first half of the film as a blubbering emotional wreck when his girlfriend (the eponymous Sarah Marshall) dumps him. Then, to add insult to injury, she happens to be staying at the same resort as him when he flies to Hawaii for a vacation. He does meet another woman and they begin to get close, but the emotional baggage from his relationship with Sarah Marshall does cause some problems with his new relationship.

* Ekaterin from the ''Literature/VorkosiganSaga'' had a relationship with her first husband that was borderline abusive. Miles has to convince her that things could be different with him. Unfortunately, he decides to approach that task as if it were a covert ops mission...

* ''Literature/TrappedOnDraconica'': Rana's isolation stems from a bad experience with her FirstLove. Specifically, [[spoiler: Daniar accidentally stole her crush, Tyrone. In truth, Zarracka killed him because she failed to steal him from Daniar.]]
* In ''Literature/TheDresdenFiles'', this is part of the reason that Karrin Murphy doesn't want to get together with main character Harry Dresden. She's been divorced twice (which is a big deal in an Irish-Catholic family like hers), and to make matters even MORE awkward, her second husband (who divorced her because he wanted a family, whereas Murphy didn't because she wanted to keep working as a police officer) later ended up marrying her little sister. As a result, she doesn't want a serious relationship with anyone, including Harry (and Harry doesn't want a casual one since he has abandonment issues, due to losing both his parents at a young age and not having a family for most of his life).

* In the ''Series/That70sShow'' episode "Your Time is Gonna Come", shortly after Jackie starts dating Hyde, she sees her previous boyfriend Kelso kissing with his new girlfriend, and - in the presence of Hyde - screams: "GET OFF MY BOYFRIEND!" In the next episode, she tells Hyde that she may have "leftover feelings" for Kelso "but what am I supposed to do? He was my first boyfriend!"
** In the episode after Eric and Donna break up, Eric asks Red how he felt after his first break up, Red says that it hurt but he sucked up and moved on right away. [[{{Flashback}} Cut to a younger Red]] in his navy uniform breaking down in tears when he recounts his first girlfriend.

* In ''Series/DoctorWho'''s television revamp, the Doctor spends a whole lot of time dealing with Rose's departure, to the point that Martha spends most of her season feeling like an in-universe ReplacementScrappy.
* After Angel left, [[Series/BuffyTheVampireSlayer Buffy]] had a very hard time moving on. It didn't help that her first attempt was [[TheCasanova Parker.]]
* In ''Series/{{Dexter}}'' Dexter and Rita's relationship is slowed by her BrokenBird status due to her [[DomesticAbuse 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|2008}} 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.

* 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.

* The primary reason Aribeth is ObliviousToLove in the second chapter of ''VideoGame/NeverwinterNights'' is that she hasn't gotten over Fenthick yet. He [[spoiler: had just been executed as a traitor a few months ago, at best.]]
* In ''VideoGame/FinalFantasyVII''. Aerith asks Cloud if he'd ever met Zack who was also SOLDIER First Class. Several side stories in the game provide more information on him and, until her death, each has a clear impact on Aerith. Furthermore, it turns out that Zack was her boyfriend, who was part of a Shinra experiment along with Cloud and whose history Cloud adopts as his own memories, creating a triangular influence of the ex on her current attempt at a relationship.
* 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."
** Another reason she resists becoming attached to anybody is that she broke the heart of one of her former lovers when she left him. She still feels guilty about it.
** Varric also has this in his backstory, although it doesn't become readily apparent until the comic ''Until We Sleep'' and the events of ''VideoGame/DragonAgeInquisition''. Seems he was left at the altar, and his ex is married to someone else, but there's still a lot of emotional baggage.

* Lon'qu from ''VideoGame/FireEmblemAwakening'' suffers from a very extreme example of this. Because [[spoiler: he couldn't protect his OnlyFriend and FirstLove Ke'ri from being killed by bandits, and was blamed by her parents for her death]], he now freaks out when ''any'' woman [[CannotTalkToWomen gets too close for his liking.]]
** Cordelia is the second character with the same problem. Among [[BrokenAce several]] [[SurvivorsGuilt other]] [[HeroicSelfDeprecation reasons]], she is depressed because she is in love with [[spoiler: Chrom]] but CannotSpitItOut to the point she has no dialog supports with him. She agonizes over him to the point she believes she won't be able to love again, but she can ultimately be paired up with a SecondLove. [[spoiler: One of them being the aforementioned Lon'qu.]]
* 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]]

* In the ''Series/That70sShow'' episode "Your Time is Gonna Come", shortly after Jackie starts dating with Hyde, she sees her previous boyfriend Kelso kissing with his new girlfriend, and - in the presence of Hyde - screams: "GET OFF MY BOYFRIEND!" In the next episode, she tells Hyde that she may have "leftover feelings" for Kelso "but what am I supposed to do? He was my first boyfriend!"

** This also occurred with Barney. He gave up the idea of relationships ever being more than one-night-stands after he had his heart crushed by his long-term college girlfriend Shannon, who he thought he would marry but who ended up cheating on him and leaving him for another guy.

* Used with irony in ''Roleplay/DinoAttackRPG''. After Amanda, Rex's first love, was thought to be killed by Fogel, Rex was left so distraught by the experience that he rebuffed the affections of another... only to later realize that the one he was rebuffing was actually a very-alive Amanda!

* Implied in ''WesternAnimation/TotalDramaPresentsTheRidonculousRace''. Emma is nervous about getting into a relationship with Noah because of a bad break up with her ex Jake, which was three years prior. While's it's never stated whether or not it was her first love or not, the trope still applies.

* ''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 number of official relationships he has ''skyrockets'' after this (and [[spoiler: that time he died and came back, but that's a different trope]]).

* In ''Manga/AkatsukiNoYona'', Yona's longtime crush on Su-Won and his subsequent murder of her father and his betrayal has left her with serious emotional baggage. So much that [[spoiler: when she started slowly developing feelings for her ChildhoodFriend Hak, she doesn't even notice until she's ''well'' past the crush phase.]]

* 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.

* ''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 subsequently 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]].

* 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 catalysts for him deciding to turn Equestria into a WorldGoneMad.

** 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.

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