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Thriving Ex-Crush

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People don't always pursue a relationship with someone they are attracted to. There could be any number of reasons, from insecurity, the other person simply being from a different social class or standing, or a choice to pursue a career/academia over a relationship. The reason itself doesn't ultimately matter. What matters is, the relationship either never happened, or ground to a screeching halt.
Then there are the cases of long-term relationships, especially marriages, that fall apart, resulting in separation/divorce. Usually not of the Amicable Exes variety.
Years pass, and the two people encounter each other again. Only for our POV character to discover that the person they chose not to pursue is living a much better life than they are, and much happier. It could be part of It's a Wonderful Plot, Yet Another Christmas Carol, or a school reunion episode.
The sting of the trope is in the idea that our POV character had hoped their unrequited crush/ex was doing just as miserably, or worse, than they were, only to find that they had done very well for themselves, despite, or in some cases, even because they did not pursue the relationship.
In some stories, we meet the parted former partners through the eyes of other characters, with one living in squalor, while the other is doing quite well for themselves. This is especially common in episodes that feature a Custody Battle and might be the motivator in a murder mystery, though the downtrodden half of the exes is just as likely to be a Red Herring.
May involve Success as Revenge.
May overlap with Girl Next Door Turned Superstar. Compare: The One That Got Away. See also "Better if Not Born" Plot for an exaggerated version. Also related to Woman Scorned, Driven by Envy, and Tall Poppy Syndrome.
Compare I Just Want My Beloved to Be Happy, if the character is pleased to see their ex doing well. Will often be the victim of a Fair-Weather Ex.
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Gilmore Girls: This trope is cyclical and an integral part of what makes Rory and Jess Star-Crossed Lovers. When one is doing well, the other is doing poorly, and it's used to demonstrate that they can't get the timing right. Jess originally leaves town after being told he can't graduate due to truancy, while Rory is bound for Yale. He returns twice in season 4, but is still in a bad place while Rory is doing comparatively better, even if she's struggling at Yale. In season 6, he returns full of Character Development and a novel he'd written, having made something of himself in part due to her belief in him. He finds that she has dropped out of Yale, is living with her grandparents, and dating a rich playboy who'd rather party than study. He manages to shake some sense into her, which prompts her to re-enroll at Yale and start putting her life back together, but it doesn't last. In the 2016 revival, Rory has graduated Yale but is unemployed and adrift, while Jess is still working for his publishing company and seemingly stable. He again helps her by giving her inspiration for her next project, and the reboot ends on a Maybe Ever After as she excitedly shows him the first three chapters of her memoir, says goodbye to Logan for real, and Jess is implied to still have feelings for her.
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AoHaru Manga Library: This is usually Keiichi's position in the end if he has a Gold Digger ex-girlfriend. After struggling and getting dumped cruelly in the beginning, Keiichi manages to persist and continue to work hard, eventually striking it rich. That's the cue for the ex-girlfriend trying to get back to him because of his newfound wealth, and Keiichi rejects them.
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Olivia Rodrigo's song "good 4 u" is about discovering that her ex is doing much better without her, and hating that she's stuck on him and can't move on as easily.
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In some Sekai No Fushigi stories, the protagonist will be dumped by their Gold Digger partner when the partner believes the protagonist isn't wealthy enough or is about to hit some financial struggles. After getting over their rejection, the protagonist moves on to rebuild their life, usually by starting their own company, and gets a more loyal and loving Second Love. The original partner will try to get back with them when they find out about the protagonist's successes, but they will be rejected. A few examples include:
She dumped me right after my company went bankrupt: Neina dumps Tsukasa after his company went bankrupt, causing her to date Yatsuo, Tsukasa's former friend who now works at a big company. The couple also looks down on Tsukasa for working in a convenience store, causing Tsukasa to get another job in Tokyo at an obscure entertainment company. Years later, Tsukasa returns to his hometown to find out that Neina had married Yatsuo, but he became jobless after the president and executives of his company were arrested for running a scam, she also asks Tsukasa to take her back, only to find out that he already has a fiancée, Erika, who is also a popular idol. Turns out while living in Tokyo, Erika was originally Tsukasa's next-door neighbor, and only sang in live music clubs. Tsukasa convinced Erika to go pro, bringing success and growth to Tsukasa's employer. Erika and Tsukasa marry, while Neina and Yatsuo are constantly arguing while trying to raise their son.
I was going back home on the bullet train when I met my rich ex?: Miki breaks up with Riku when she finds out that he is poor, and she also starts making fun of him for the remainder of their school years. Several years later, she continues to make fun of him and brag about being engaged to a businessman named Makabe. However, Makabe reveals that Riku is far more successful than him. Makabe later breaks off the engagement with Miki and she attempts to get back with Riku, unfortunately for her, he is already engaged to someone else.
Ex-wife dumped me for my client company's CEO until I reunited with my childhood friend: Hayato's ex-wife cheated on him with a CEO because he didn't earn enough money for her. When her new husband's company went bankrupt and Hayato became rich after Tomo helped him out, she attempts to get back with him, only for him to reject her as he goes on a double date with Tomo and two women.
My ex-girlfriend came running back after she found out how much money I had...: May broke up with Rick after he couldn't get ahead with his accessory business. However, his childhood friend Alice helps him with his business. May comes back to beg him to take her back, only to be put in her place by Alice.
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Castle (2009): In "Murder Most Fowl", the abduction of a child leads to his father, Dean Donegal, a janitor, who was recently divorced and living in a small, one-bedroom apartment and "looking up at broke" after the divorce. Then Castle and Beckett meet his ex-wife, who married a wealthy doctor "before the ink dried" on the divorce papers. Dean isn't the murderer/kidnapper, however. His child was targeted because his job gave him an all-access pass to secure areas at a financial firm.
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The Hike (2023): Helena confides in Maggie that it upsets her to know her ex-boyfriend Robert - who she once hoped to marry - is now happily engaged to someone else and a doting father to his baby daughter. Originally, they both agreed they didn't want children, but Robert later admitted he'd changed his mind. Although the break-up was amicable, Helena tells Maggie that seeing how happy Robert is with his family made her realise that maybe she could've happy having children with him too, but it's far too late now. Helena hasn't had a serious relationship since breaking up with Robert and is deeply conflicted when she finds out she might be pregnant from a random hook-up. She keeps the baby and raises her son as a single parent.
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The Turnpike Troubadours song "7 & 7" makes use of this trope in one verse.
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An episode of Everybody Loves Raymond sees Robert Barone happier and settled, having gone past NYPD Sergeant to promotion to Lieutenant, and considering marriage with Amy. His ex-wife Joanne, who is implied to be struggling, sees this and makes a determined bid to get him back. Robert declines her.
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In the first part of Moscow Does Not Believe in Tears, Rudolf, a cameraman, dumps Katya (after sleeping with her and getting her pregnant) when he learns she is a Country Mouse who failed the enrollment exams at the university and is forced to work an exhausting menial job at a plant. A twenty-year Time Skip later, he is still stuck as a cameraman but finds out that Katya is now a member of Moscow's city council and plant manager. Soon, he tries to get back into her life and get to know his daughter; neither of the women is very impressed.
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Played with in Rent-A-Girlfriend. The beginning of the story has protagonist Kazuya being dumped by his girlfriend of one month, Mami. While Mami is wealthy, a socialite, and does not want for masculine attention while Kazuya is a meek loser, Mami finds herself furious when she next sees him with the downright gorgeous and courteous Chizuru Mizuhara and conspires to break them up. Little does she know that Kazuya is only renting Chizuru's services as a rental girlfriend and is still the loser he was when he was with her.
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Cher Lloyd's song "Want U Back" is about Lloyd feeling bad when she watches her ex doing much better with his new girl. When they broke up, she thought he wouldn't take it well but now that he's doing much better than her, she wants him back.
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M*A*S*H: "Dear Dad... Three" references this trope. While watching a home movie, Henry explains to Hawkeye and Trapper that his wife Lorraine had been dating quarterback Buzz Walinski when they first met. Walinski, Henry notes, went on to own the biggest cement contracting company in the state. Hawkeye quips that Henry saved Lorraine from a life of prosperity.
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Synépeies - A Collection Of NTR Consequences: A few times, the cheating woman who left the male lead for the antagonist will try to win the lead back after her old relationship went sour, only to discover the lead has already found a Second Love who is much more loyal:
In Fallen Leaves, Amamiya Kaede, who sided with her rapist Coach Marada and dumped Sugimura Yuuichi for him, tries to get back together with him after Marada's activities were exposed and her reputation went downhill for helping cover it up. Marada even went so far as to tell her that Yuuichi was a struggling loser, only for her to discover that was a lie and Yuuichi is actually a successful worker with a nice house and a fiancée. She begs him to take her in anyway, only for him to tell her off and kick her out of the house.
In Hitorijime Undone, Akina decides to seek help from Kouta, her childhood friend whom she rejected in favor of buff, macho Tatsuya, when their Awful Wedded Life in a dingy apartment, constantly changing jobs, and incoming eviction becomes too much for her to bear. She then discovers that Kouta has since become a wealthy banker with a loving wife and beautiful daughter. Hiyori, his wife, is willing to let Akina become their nanny, but does so specifically to torment Akina with the happy, wholesome family she could have gotten but turned down by breaking Kouta's heart, and Akina indeed spends the rest of the story stewing in jealousy and regret.
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 Synépeies - A Collection Of NTR Consequences (Fanfic)
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There's a Pokémon fancomic where all of Ash's female companions turn out to be doing much better for themselves ever since they stopped hanging out with him. Ash himself is sincerely happy for them (being perennially 10 probably helps with that), Brock less so.
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Love Tyrant: Akane's mother, Suo Hiyama. She has zero tolerance for love in general and attempts to force Akane to break up with Seiji. This is the result of her former husband having moved on from his previous life with her and getting remarried after she decided to prioritize her family's assassination business over what she really wanted, and she became bitter about that. She's later chastised about this by Ameisha, both her rival in business and love as she's the one her ex-husband is currently married to.
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A Christmas Carol: Scrooge is shown by The Ghost of Christmas Past that Belle, who had broken up with him because of his greed, was now happily married and with children and a loving, doting husband. Scrooge, meanwhile, is a solitary miser whose only family left is his nephew, whom Scrooge chooses to avoid, at least until his reformation.
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 A Christmas Carol
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In her Saturday Night Live song about monologing, Taylor Swift sings about her ex who broke up with her over the phone assuring him that she is doing just fine hosting the Saturday Night Live show.
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The Mark Chesnutt song "All My Old Flames Have New Names" has the protagonist trying to hook up with his old lovers from long ago, only to find out that all of them have settled down and moved on with their lives.
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In Dogma, Bethany's husband left her when she was unable to give birth, and didn't want to adopt. He got married and had children. Later, the angel Bartleby tells her that he's perfectly happy without her.
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Played both straight and platonically in Runaways (Rainbow Rowell):
Prior to the events of the series, Nico quit the team, unable to cope with apparent PTSD, and Karolina, with whom she shared years of Unresolved Sexual Tension, got tired of waiting for her to come back and went off to college. In the present, she's now rich again (because of royalties from her late parents' movies), has a girlfriend, and is on her way to becoming a social worker, while Nico is broke and stuck working retail. Subverted when Karolina, feeling guilty about Nico's plight, drops out of college to rejoin the Runaways to keep Nico from ending up alone again, which naturally causes her girlfriend to dump her.
Sometime after Nico quit, Molly discovered that she had a still-living grandmother, who adopted her, and thus she abandoned Klara. Heartbroken by her best friend's departure, Klara quit the team and went into foster care. When the team goes to recruit her, they're shocked to discover that she's now a Jewish American Princess, with a nice house and two loving, doting foster dads. Molly, whose grandmother turned out to be a supervillain, leaving her with no choice but to rejoin the Runaways in near-poverty, does not take this well and ends up depressed for most of the series.
The final issue reveals the fate of Karolina's ex-fiancee Xavin, who was last seen being taken into custody for war crimes against Majesdane: They managed to successfully argue that they were innocent of the crimes, joined the Majesdanian military, and became a General.
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The Bolt Chronicles: Inverted in "The Party." Mittens bumps into Tom several months after having had a tryst with him during the story "The Clouds." In that earlier fic, he is a strapping, hunky street stray who has a one-night stand with Mittens and then ignores and abandons her the next morning. Since then, he has been rescued from the streets and neutered, then adopted by a family who grossly overfeeds him, turning the tomcat into a morbidly obese Big Eater and Lazy Neutered Pet. Mittens is embarrassed by him and feigns an excuse to leave.
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In the As Time Goes By episode "Lionel's Ex-Wife", the titular Margaret contacts Lionel out of the blue and invites him out to have a drink; she is very different now, glamorous, lavishly dressed, and with a handsome young boy toy. At the end of the episode, Margaret openly admits to Lionel and Jean that invoking this trope was her main reason for getting in touch.
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Maddie & Tae's "Well In Your World" hopes this for a high school sweetheart. She doesn't want him back (and knows he doesn't, either), she was just thinking about him and their relationship and hopes he's doing well.
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Cobra Kai: Played with. In the 30+ years since the events of The Karate Kid (1984), Johnny's remained a dead-end loser who peaked in high school and never left LA, while his old girlfriend Ali has gone on to become a pediatric surgeon in Denver. They reconnect at the end of Season 3, and Johnny confesses that he feels like he wasted his life compared to her. Ali replies that her life hasn't been without mistakes and that her marriage is on the rocks.
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The following is a list of statements referring to the current page from other pages.

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Love Interests
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The Ex Index
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