The First Cut Is the Deepest
"I would have given you all of my heartAlice and Bob have been growing closer and closer, possibly leading up to a Relationship Upgrade...only there's a problem: Alice's ex, Charlie. No, it's not that Alice is still in love with Charlie, it's that the fallout from her relationship with Charlie has left her with serious emotional baggage that must be worked out before any new relationship can succeed. Can also happen when Charlie is dead and Alice still has grief issues to work out. Will often culminate in an Epiphany Therapy session between Alice and Bob, where Alice spills all her baggage. If the emotional baggage is not worked out, Alice and Bob may become an Anchored Ship. Not to be confused with the trope about the first time you literally cut someone being the hardest.
But there's someone who's torn it apart..."
But there's someone who's torn it apart..."
— Cat Stevens
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Anime and Manga
- Fruits Basket - Hatori's past relationship with Kana has this effect on him, and oddly enough, somewhat on Mayuko, his new flame, as well; she was Kana's best friend and clearly a Shipper on Deck, even though she was in love with Hatori the whole time, and thus she feels that she'd be betraying Kana if she got together with him.
- InuYasha's past relationship with Kikyo causes this between him and Kagome...at least early on. When Kikyo is resurrected it becomes a whole new can of worms.
- At the beginning of Kodomo no Omocha, 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.
- Kyoko's dead husband Soichirou on Maison Ikkoku. Comparisons to Godai happen all the time. And as many readers fail to understand, when Godai and Kyoko do get together, it's not just because Godai has matured from a boy to a man, but because Kyoko has worked through her baggage with Soichiro enough to be able to fully pursue a relationship with someone else. Also, a big point of Godai's maturation is recognizing this trope; Kyoko may be over Soichiro enough to be able to get with Godai, but she'll never fully be over Soihirou, and he'll have to accept that if he wants to be with her.
- The Wallflower - 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 Anchored Ship.
- Kyoko from Skip Beat! swore off love after finding out how her childhood love Sho was just using her to further his career, and this is the main reason for her being utterly oblivious to Ren's feelings for her.
- GE - Good Ending has the main female character Kurokawa repeatedly plagued by the shadow of her ex-boyfriend, which keeps on haunting her even after she successfully gets together with Utsumi.
- High School DXD has the protagonist Issei unable to even think that the girls in his harem love him at all despite them even outright doing things in front of him, short of sex, is because he still has the scars from his ex-girlfriend. Specifically, the get killed by his first girlfriend and said girlfriend was bored of him.
- A bad breakup with his first girlfriend Athena as well as the ideas she drilled into his head have made Hayate in Hayate the Combat Butler highly reluctant to even consider the idea of dating anyone in the foreseeable future.
- What happened to Yoko Littner in Tengen Toppa Gurren Lagann. Having lost her first great love (Kamina) right after their First Kiss and Love Confession will understandably make a person reluctant to get romantically involved afterwards. And it's worse when you recall that it happened twice: Kittan gave her a Last Kiss and a sort-of Love Confession right before his massive Heroic Sacrifice.
- The manga version of Sailor Moon 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 swore off men, partly because of this and partly 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 Codename: Sailor V:
- 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, they were exactly 5,000);
- number 5,000 of Minako's crushes, Ace, was also her true love. After, as expected, he died in the final chapter because she found out he was Kunzite's subordinate and killed him, Minako swore off men because they were in the way of her duty (Minako's possible love with Rei doesn't count because she's a girl and it doesn't get in the way of duty).
- Evangelion 303: Discussed. 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.
- Hunting The Unicorn, being a Deconstruction Fic of the But Not Too Gay portrayal of Kurt and Blaine, uses this to heartbreaking effect; Blaine lost his virginity at 16, when he believed and tried to invoke Sex Equals Love. 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 Ben 10 fanfic series 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 And The Story Continues. Interestingly, L and Erin didn't have an actual intimate relationship 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.
Films — Animated
- Hercules - Megara's first boyfriend really soured her on men.
- In Ice Age 2: The Meltdown, this pops up when Manny admits that he is finding it hard to love Ellie because of his loyalty to and memories of his First Love.
- In Wreck-It Ralph, Sergeant Calhoun had the most Tragic Backstory ever — her beloved boyfriend died at the altar and during their wedding because she forgot to do a perimeter check for escaped Cy-Bugs. Really painful when Felix, moving into Second Love, 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 Heroic BSOD.
Films — Live-Action
- Enchanted - Robert's divorce effectively killed his belief in romance until Giselle came along.
- Just Like Heaven 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.
- In the 2008 film Get Smart, Agent 99 had this due to her bad breakup with Agent 23.
- The Princess Bride - After Westley's death, Buttercup vows to never love again. Luckily for her, Westley's not actually dead.
- In Red Eye, Rippner tries to guess Lisa's reason for her implied solitary nature and distance from men, mockingly asking her if someone broke her heart. Lisa was raped.
- A variation on this trope is seen in The Ugly Truth. 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.
- In Forgetting Sarah Marshall, 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.
- The Trope Namer is the song by Cat Stevens, which has been covered by P.P. Arnold, Keith Hampshire, Rod Stewart, and Sheryl Crow, describing just this kind of situation.
- The 1990s Cantopop song Soothe My Wound is as much as on this topic as the example above when Alice and Bob are already on the bed, as exemplified by the refrain:
But I'm growing wary of this gameIt's not easy to forget the past when we're closeThe person who stole my passion in the pastdid also romantically promised me
- Eminem's "Space Bound":
If you fuck me over, 'cause if I get burnt I'ma show yaWhat it's like to hurt, 'cause I've been treated like dirt before ya
- "The First One" by Boys Like Girls:
The first one is the worst one when it comes to a broken heart.
- Harry Potter features this in book 5. Harry starts to date Cho Chang, and everything is going well until Cho has a breakdown over the death of her ex, Cedric Diggory— whose death Harry witnessed and could not avert. It takes her several years to get over it enough to get more or less Happily Married to a Muggle guy.
- Dumbledore had this as part of his backstory. Though it never directly came up in the books, J. K. Rowling revealed all the details to the public. The man who broke his heart was none other than Gellert Grindelwald, a 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 cause him to again completely lose his moral compass.
- In Rebecca, the female protagonist believes that her husband Maxim is still carrying a torch for the titular Rebecca, his exalted dead first wife. Subverted when she learns that the beloved Rebecca was actually a Manipulative Bitch who Maxim hated.
- Ekaterin from the Vorkosigan Saga 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...
- Arya in the Inheritance Cycle 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 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.
- Trapped on Draconica: Rana's isolation seems from a bad experience with her First Love. Specfically, Daniar accidentally stole her crush, Tyrone. In truth, Zarracka killed him because she failed to steal him from Daniar.
- In The Dresden Files, 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 her's), 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 Pact, Blake Thorburn has an instinctive fear of intimacy or physical contact, stemming from his time spent homeless, when he joined a Cult where sex was used by the cult leader as a tool of manipulation, deceit, and control. He escaped, but has some complicated feelings about it, and thinks of himself as a flawed, broken person as a result.
Live Action TV
- 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.
- Also occurs, surprisingly enough, with Casey. He still carries a great deal of grief over the 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 his fiance, Kathleen Mc Hugh, 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 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.
- In the That '70s Show 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!"
- While it's not the first cut, Ted from How I Met Your Mother has to eventually admit that being left at the altar gave him some serious emotional baggage to deal with.
- Though he did get a first cut too — the girl he lost his virginity to in high school pretended she loved him to get him into bed, ran out on him the moment they finished the deed, promised to call and didn't, and borrowed twenty dollars that she never returned.
- 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.
- Again, while not the first cut (but certainly the first the audience sees), Ted's feelings for Robin have come and gone as a major source of conflict in his search for the mother, especially through the later seasons.
- 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.
- In Doctor Who'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 Replacement Scrappy.
- After Angel left, Buffy had a very hard time moving on. It didn't help that her first attempt was Parker.
- In Dexter Dexter and Rita's relationship is slowed by her Broken Bird status due to her ex-husband. Unusually for this trope, Dexter chose to date her because of this as it left her, like him, uninterested in sex.
- Merlin starts his series as a teenage boy who has a Meet Cute 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. It ended with her bleeding to death in his arms. Ever since that, he's been utterly uninterested in women, and Word of God confirms he's mostly asexual now.
- 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 Janice and Kathy did a lot of damage. While he already had Commitment Issues, 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 Secret Relationship. Even when they were married, he was an Insecure Love Interest and worried she'd leave or cheat on him, despite her being the most reliable of the friends gang and obviously crazy about him.
- Monica herself took months to recover from her First Love Richard, who she broke up with because he didn't want children. She later admitted that getting over him was the hardest thing she ever had to do. This knowledge haunted Chandler, (see above) although Monica promised that he was now the love of her life and even when Richard asked her for a second chance, chose Chandler instead, plainly showing that she'd moved on.
- On The 100, Clarke briefly returns Lexa's kiss, but says she's not ready to be involved with anyone yet, since her last romantic partner died at her hands not too long ago.
- Parodied in a round of I'm Sorry I Haven't A Clue as a comment on the habits of builders making estimates for jobs:
The first quote is the cheapest...
- Used with irony in Dino Attack RPG. 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!
- The primary reason Aribeth is Oblivious to Love in the second chapter of Neverwinter Nights is that she hasn't gotten over Fenthick yet. He had just been executed as a traitor a few months ago, at best.
- In Final Fantasy VII. 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 Dragon Age II 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 because she broke the heart of one of her former lovers when she left him. She still feels guilty about it.
- In Assassin's Creed: Brotherhood, it's possible to unlock Ezio's Repressed Memories of his first love Cristina Vespucci and their relationship, which ultimately does not pan out well.
- Lon'qu from Fire Emblem Awakening suffers from a very extreme example of this. Because he couldn't protect his Only Friend and First Love Ke'ri from being killed by bandits, and was blamed by her parents for her death, he now freaks out when any woman gets too close for his liking.
- Cordelia is the second character with the same problem. Among several other reasons, she is depressed because she is in love with Chrom but Cannot Spit It Out 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 Second Love. One of them being the aforementioned Lon'qu.
- MegaTokyo - Erika's past with Hitoshi made her the Broken Bird she is today, and caused serious problems when she and Largo began to strike up a relationship.
- Lately, Kimiko seems to be insinuating that Piro's past with Miho will have to be resolved before the two of them can move forward.
- Non-ex example in Questionable Content. Faye can't reciprocate Marten's affections (though she really wants to) because of her issues as a result of seeing her father commit suicide. They do get an Epiphany Therapy session, but then become an Anchored Ship since she still has things to work out. Most fans consider the ship fully sunk after both Marten and Faye moved on to other love interests.
- Avatar: The Last Airbender - Yue's departure had this effect on Sokka, leading him to be overprotective of his new girlfriend. Culminates in "The Serpent's Pass."
- In Kim Possible, Kim was cool with her old flame Josh dating Tara, but the second cut was the deepest: when Eric turned out to be one of Drakken's synthodrones, it nearly broke her, until Ron snapped her out of her depression.
- Actress Donna Dixon famously broke the heart of KISS frontman Paul Stanley when she left him for Dan Ackroyd. It took Stanley a long time to recover from that breakup, and it inspired him to write the breakup song "I Still Love You."
- Also, for those tropers who had a recent break up with your first boyfriend/girlfriend, it's something perfectly normal, you'll find another one. Believe it.