The First Cut Is the Deepest

"I would have given you all of my heart
But there's someone who's torn it apart..."

— Cat Stevens, "The First Cut Is the Deepest"

Alice 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. Compare The Mourning After, if the ending of the relationship was particularly traumatic.

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Examples:

Anime & 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.
• 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.
• 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. While he does eventually work through this, he still ends the series single. At least so far as the reader can tell, anyway.
• High School D×D 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 Despair Event Horizon 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 Fallen Angel 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 that time he died and came back, but that's a different trope).
• 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. Inuyasha and Kagome eventually get together only after Kikyo wants Inuyasha to live on after she is able to die peacefully and she acknowledges Kagome as her successor. A large portion of the series is devoted to Kagome coming to terms with Inuyasha never being able to get over Kikyo and her own jealousy towards their unbreakable bond. Apart from Inuyasha and Kikyo being deeply in love, it doesn't help that they were almost married but tricked into betraying each other and Kikyo lived an incredibly tragic life (and afterlife).
• In Jagaaaaaan, Robahata fell in love with Karen, but some misunderstandings about their relationship and seeing her having sex with someone who hurt her feelings drive him over the edge. Even as he becomes a serial rapist who brainwashes girls into being addicted to having sex with him, it's clear that he's still extremely hurt by Karen's seeming betrayal. In his last moments, he comes to realize that he still loves her deeply and dies wanting to reunite with her.
• At the beginning of Kodocha, 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 from 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 Soichirou, and he'll have to accept that if he wants to be with her.
• Rudeus of Mushoku Tensei: Jobless Reincarnation is devastated when Eris disappears after their first night together, leaving a vaguely-worded note. Thinking he was somehow inadequate, for several years he's unable to feel aroused and it interferes with his next relationship.
• 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 sworn 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, there were exactly 5,000).
    • Number 5,000 of Minako's crushes, Ace, was the most painful of her infatuations. 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.)
• 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.
• 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 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.
• In Yona of the Dawn, 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 when she started slowly developing feelings for her Childhood Friend Hak, she doesn't even notice until she's well past the crush phase.

Fan Works

• Accursed Ones: While Anders and Hawke are mutually attracted to each other, Anders is still grieving over Karl, as well as his lost cousin Amell; in fact, one of Anders' private reservations is his fear that he might be using Hawke as a Replacement Goldfish for Amell due to their strong resemblance.
• In Bride of Discord, 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 World Gone Mad.
• Classroom of the Elite: Liquid Inspiration has an Implied case with Atsuomi. After failing to win the heart of an unnamed woman from his past, he dedicated himself fully to climbing the Japanese political ladder. His brief marriage to Mika and their son together are nothing more than part of those ambitions.
• Dear Diary: Cenn's first love was a Literal Maneater who tried to devour him, leaving him leery of pursuing any other romantic possibilities.
• Derailed: After her romance with Discord turned out poorly, Princess Celestia completely left the dating scene and has been going without for roughly a millennium. Her sister Luna thinks that she needs to get back on the market and gain some proper experience.
• Discussed in Evangelion 303: 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.
• In Heartfelt Gifts, everyone can infuse bits and pieces of their feelings and emotions into any gifts they prepare for others so that their recipients can feel how much they care. In exchange, they can feel how much the recipients truly appreciate their gifts. While Marinette repeatedly infuses all of her gifts for Adrien with her emotions, however, she never receives anything in return. Eventually, this reaches the point where her feelings for him are completely exhausted — having given away all she had and gotten nothing in return, there's simply nothing left in her heart for him. Afterwards, it takes time for her to even consider tapping into her emotions for anybody else.
• 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.
• 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 him being married to someone else.
• Horde Champion: Anevay gets a lot of self-worth and abandonment issues after Alina angrily ends their 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.
• In Inside Man, Buffy confides in Spike about how everything that happened with Angel made her reluctant to open up to anyone else, partly because she didn't want to get hurt again and partly because she was holding onto hope that she and Angel would eventually be able to get back together. However, she eventually came to realize how naive that was:
  Buffy: That love wasn't good love. It almost killed me and I almost let it.
• Old West: 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 Rattlesnake Jake, she's hesitant to reciprocate out of the fear of history repeating itself.
• The One I Love Is...:
  • In chapter 6, Rei is trying to convince Shinji to get over his feelings towards Asuka and suggests he talk to Kaji because the older man was in a relationship with Misato and she thinks he will make Shinji understand he has to move on and forget about the past... not knowing Kaji never got over Misato.
  • After the last battle, Misato and Makoto started dating. However, Shinji thinks his guardian can not completely love Makoto because she never stopped loving her first lover.
• Opal, Sapphire, Ruby, and STEVEN!: While Amethyst has fallen in love with Pearl, Pearl is still yearning after Rose Quartz and simply isn't ready to enter a relationship with anyone else yet.
• In PostMU: Life's a Scream!, Terry Perry has this problem. As it turns out, he was head over heels for an Alpha Bitch in high school who ultimately wasn't content with just breaking his heart but gleefully shredded not only his social life but his brother's as well so thoroughly the twins had to change school. Needless to say, he's slow to warm up to girls in general and romance isn't remotely on his radar.
• Second Chances (TheNovelArtist): 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.
• Sehnsucht: The only person Cynthia ever loved romantically was Daemon Spade, who was in love with her adoptive sister. Out of respect for their relationship, Cynthia never confessed her feelings, though it's implied he was aware. Then Elena died, which utterly broke Daemon and led to him betraying the First Generation. Cynthia loved him too much to fully punish him for this, and the memories of this tragic relationship haunt their reincarnations, to the point that she shows no interest in romance in her second life either.
• Skyhold Academy Yearbook: Varric's romantic history is the same as it is in the games, with an ex who broke off their engagement and left him with emotional baggage. However, this doesn't actually get mentioned until close to halfway through the series, and his ex only makes a brief appearance in one chapter. It's eventually explained that his work at the eponymous school has helped him deal with the lack of closure. Finding his Second Love helps too.
• Synépeies - A Collection Of NTR Consequences: In Hitorijime Undone, while we never see it, Kouta's new wife Hiyori briefly says to Akina, his childhood friend and first crush, that this was the result of her rejecting him and that it took a while for her to help him get over her.
  After you chose to be with that sorry excuse for an anthropomorphic trash can, do you know how long it took for Kouta to even look at another woman? Two years. Two years where, no matter how hard I tried to be there for him, he could not get you out of his heart. You were his world, Akina, and you shattered it almost beyond repair. I’ll never forgive that.
• There's More Magic Out There features an indirect version: Alya's mother was a Selkie whose husband stole her skin in order to force her to become his wife. She eventually ran away with her two daughters, Nora and Alya, then met Otis and had the twins with him. Alya subsequently worries about revealing her selkie side to Nino or anyone else, fearing they might turn out to be just as bad as her Glorified Sperm Donor.
• Truth and Consequences: Adrien wanted nothing more than to be taken seriously as a superhero, rather than treated as though he was nothing more than Ladybug's sidekick. Then Ladybug struck a deal with Hawkmoth in hopes of protecting him from the Awful Truth about his father. Come the sequel, Mending Warped Designs, and Chat Noir is finally regarded as a hero in his own right... but he's leery of trusting anyone else like he used to trust Ladybug.

Films — Animation

• Hercules - Megara's first boyfriend, an Ungrateful Bastard who dumped her after she sold her soul to Hades to save him, really soured her on men.
• In Ice Age: 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 Back Story ever — her beloved boyfriend died at the altar 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.
• 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.
• In the 2008 film Get Smart, Agent 99 had this due to her bad breakup with Agent 23.
• James Bond:
  • Following the death of Tracy on their very wedding day in On Her Majesty's Secret Service, Bond never remarried nor pursued long-time relationships in the (rather Broad Strokes) continuity of the 1962-2002 series.
  • For the Daniel Craig films, the death of Vesper Lynd at the end of Casino Royale caused this, at least for the two following films, Quantum of Solace and Skyfall. By Spectre and No Time to Die he has found a Second Love in Madeleine Swann, though he still goes to Vesper's grave in Matera to be at peace once and for all.
• 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.
• 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 that 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.

Music

• 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.
• "All My Gold" by Bat for Lashes:
  There was someone that I knew before, a heart from the past that I can not forget
  I let him take all my gold and hurt me so bad, and now for you, I have nothing left
• "The First One" by Boys Like Girls:
  The first one is the worst one when it comes to a broken heart.
• 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 game
  It's not easy to forget the past when we're close
  The person who stole my passion in the past
  'did also romantically promised me
• Eminem's "Space Bound":
  If you fuck me over, 'cause if I get burnt I'ma show ya
  What it's like to hurt, 'cause I've been treated like dirt before ya
• Juice Newton's "The Sweetest Thing I've Ever Known" subverts the trope: their experiences with worse people makes the lovers appreciate each other more.
• In the Meat Loaf song "Two Out of Three Ain't Bad" the singer laments that he can't love another girl (no matter how much he needs and wants her) because his last girlfriend broke his heart irreparably.
• Nautilus Pompilius: In the song "Thirst", the lyrical hero still can't forget his first love.
• "This Cut is the Deepest" by Swallow the Sun
  You are nothing but a shadow of the beauty what you used to be.
• "Another Love" by Tom Odell is all about this. The singer desperately wants to show his new partner how much he cares, but has difficulties with this because he's still deeply hurt by a previous relationship.
  And I'd sing a song, that'd be just ours
  But I sang 'em all to another heart
  And I wanna cry, I wanna learn to love
  But all my tears have been used up
  On another love, another love
  All my tears have been used up
• Trisha Yearwood's "The Woman Before Me" is from the perspective of the new love of a person who is struggling with the emotional trauma of a previous toxic relationship.
  But the woman before me must've been hard on you
  'Cause that hurt in your eyes I'll never put you through
  Sometimes I think you must be talking to
  The woman before me and you
• Usher's U Remind Me is how the he meets a girl, who while he likes, is an Identical Stranger down to her mannerisms to a girl who hurt him, that he's unable to be with her.

Literature

• The Chronicles of Dorsa: Joslyn's first love was a girl who didn't return her affections and ran away with a boy. She's kept a flower the girl left her as a goodbye gift for years, destroying it after telling the story to Tasia.
• 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 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).
• Earth's Children: Jondalar's first real relationship - a forbidden one with an older woman named Zolena - ended in disaster (he beat the crap out of a jealous rival who exposed his romance with Zolena, resulting in him being Sent Off to Work for Relatives) and until he meets Ayla, he had never been able to properly get over it and meet another woman he loved that deeply.
• 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 apparently 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.
• 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 realizes it at first.
• 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.
• In 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 with 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.)
• Semiosis: The sapient bamboo-like Plant Alien 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.
• Trapped on Draconica: Rana's isolation stems from a bad experience with her First Love. Specifically, Daniar accidentally stole her crush, Tyrone. In truth, Zarracka killed him because she failed to steal him from Daniar.
• In Ugly Love, Miles avoided having any romantic relationships - and didn't have sex either- for six years and insists that he and Tate keep their relationship purely physical because his relationship with his first serious girlfriend, Rachel, ended extremely badly, and he never wants to go through that pain again.
• 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...

Live-Action TV

• 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.
• After Angel left, Buffy had a very hard time moving on. It didn't help that her first attempt was Parker.
• On Choujin Sentai Jetman, 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.
• Chuck had this with Chuck and his ex-girlfriend 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 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 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.
• CSI: NY: The series opens with Mac still mourning the loss of his wife Claire in the 9/11 terrorist attacks three years prior, and still wearing his wedding band. He has his first date as a widower in the Season 1 finale, but nothing comes of it. By Season 3 he has a girlfriend but refuses to tell anyone and is still so hung up on his wife that he calls the woman "Claire" during an argument over his secrecy.
• 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.
• 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 a Replacement Goldfish.
• Forever:
  • Henry's First Love Nora, who pressured him to tell her what happened to him on the ship (his first death and resurrection), then had him taken to an asylum when he told her, which led to literal torture he eventually had to kill himself to escape. As if that experience didn't scar him enough about telling anyone his secret, decades later she reappeared, now believing in his immortality but wanting to tell the world about it, ending with her trying to shoot him in front of witnesses and killing Henry's new love interest, Anne, instead.
  • Abigail may have been Henry's second wife, but there are strong shades of this trope in his reaction to her disappearance and its effect on any potential romance with Molly or Jo, too.
  • Jo's First Love with her husband Sean ended with his unexpected death from a heart attack, and Jo turns to drinking and casual sex to bury the pain. She eventually heals, in large part thanks to Henry, enough to try dating Isaac Monroe.
• Friends:
  • Ross: Carol, his first wife (and the 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, whom 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.
  • Sixth Ranger Mike, who agrees to move in with Phoebe and be in a long-term relationship, but has no desire to re-marry after his first marriage went so bad, it soured him on the idea. This causes a rift between Phoebe (who to her surprise, does want to marry at some point) and Mike and a breakup, but they quickly reconcile when Mike realizes he loves Phoebe too much to let her go because of his insecurities.
• 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 spends most of the next eight years in mourning, never really moving on until she meets Ted.
• 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 further. 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.
• My Roommate is a Gumiho: Woo-yeo has complex feelings about Dam, the woman who now holds his fox bead and whom he is attracted to because his first love (back in the Joseon dynasty) died from it.
• That '70s Show:
  • In the episode "Your Time is Gonna Come", shortly after Jackie starts dating Hyde, she sees her previous boyfriend Kelso kissing 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. Cut to a younger Red in his navy uniform breaking down in tears when he recounts his first girlfriend.
• The Twilight Zone (1985): In "Nightsong", Andrea Fields has never gotten over her tumultuous relationship with Simon Locke, who cheated on her and often disappeared for weeks at a time when inspiration for his music struck. She still loves Simon after everything that he put her through and these mixed feelings mean that it is impossible for her to pursue a new relationship. Andrea had a very short relationship with her fellow DJ Ace Campbell but she broke it off before it could get too serious. Simon returns after an absence of five years and eventually reveals that he died in a motorcycle accident shortly after the last time that he saw her. He wants Andrea to be happy so he apologizes for mistreating her and tells her that she should let him go.
• Young Sheldon: In S4 E18, Missy experiences her first breakup. She refuses to talk to anyone about it, and instead lashes out at anyone who tries to talk to her.

Radio

• 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...

Video Games

• 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.
• Dragon Age:
  • 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 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 Dragon Age: Inquisition. Seems he was left at the altar, and his ex is married to someone else, but there's still a lot of emotional baggage.
• 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.
• Fire Emblem:
  • Fire Emblem: Awakening:
    • Lon'qu from 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.
  • In the Fire Emblem Gaiden remake, Fire Emblem Echoes: Shadows of Valentia, some characters will play this straight if their prospective love interest kicks it in Classic Mode: Mae (if Boey dies), Boey (if Mae dies), Gray (if Tobin lives but Clair dies), Clair (if Gray dies), Leon (if Valbar dies).^note (Tatiana subverts it: she plays it straight in the original, but in the remake, she eventually has a Second Love.)
• 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.
• Tales of the Abyss: You'd think that being smothered by a harem of busty ladies when he was five would turn 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 Guy Cecil cannot touch women without having a panic attack.

Visual Novels

• Played With in Daughter for Dessert. The protagonist certainly misses Lainie, and he has a sex dream about Lainie at the end of the first chapter that seems to set the stage for his relationship with Amanda. However, it’s not clear that anything gets, or needs to get, resolved regarding the protagonist and Lainie.
• Averted with the protagonist of Double Homework. While his bond with Rachel is still special, and seeing her is painful at the beginning of the story, the two of them don’t have to resolve anything for the protagonist to date and form meaningful relationships with other girls.
• Ikemen Sengoku: The main reason Kenshin initially tries so desperately to deny that he's fallen in love with the female main character, and later on goes to extreme lengths to keep her "safe" from anyone else, in his route is that his first love Isehime committed suicide after they were torn apart by his vassals who didn't approve of their relationship. Shingen notes that if Isehime had lived, he would have eventually gotten over her, but that her suicide left him with unresolved emotional scars and a lifelong fear of losing anyone else he got attached to.
• Discussed in Melody. Since his breakup with Bethany is so recent, several characters ask the protagonist if he still has feelings for her.
• In Winds Of Change, you can do this to a few characters in the epilogue depending on certain events and if you decided to pursue a romantic relationship with anyone. Should you release him from immortality before destroying the orb, Ulric becomes king but doesn't take anyone else at his side. And if you destroy the orb with a high relationship with Damek, he devotes himself to serving Ulric and it's implied few others can actually break through his PTSD.

Webcomics

• 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.

Web Original

• 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 Fan animation of Pokemon Red reveals that Misty constantly going on dates during Gen 2 was her trying and failing to rebound from Red disappearing to Mt. Silver from the pressures of fame. When Gold convinces Red to return to Kanto, the two get right back together.

Western Animation

• 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 Gargoyles, Goliath was in love with Demona and had a child with her but Demona would betray him and become a Fallen Hero, 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 Elisa (aside from the fact they are of different species) and ironically he might not have ever entertained the idea to be with Elisa if it weren't for Demona and Puck's meddling.
• 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.
• Throughout all of Miraculous Ladybug, Marinette has an enormous crush on Adrien but can't find the words to say it. In early seasons, she has difficulty even speaking in Adrien's presence. When Adrien instead approaches Marinette, she still can't find the words to return the gesture. In the episode "Derision", it gets so bad that she freaks out and yells at Adrien, apropos of nothing. It is finally explained that she once tried to start a relationship with Kim, who (at the urging of bully Chloe) played a prank on her that was enough to traumatize her.
• Implied in The Owl House. 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 Amity without a Grand Romantic Gesture.
• Implied in Total Drama Presents: The Ridonculous Race. 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 it's never stated whether or not it was her first love or not, the trope still applies.

Real Life

• 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.
• 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."

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