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Anime and Manga
- An episode of Rumic Theater has a man being invited to a school reunion by a girl he remembers having a crush on, and who might just have reciprocated, but he was transferred out before he could learn the truth. His current married life is... disappointing, and he fantasizes about having a fling while simultaneously realizing how unlikely that would be. At the reunion he meets the woman who reveals that she did have a crush on him, and is conveniently recently divorced... and is now grossly overweight, not one bit pretty and a sloppy drunk. He decides to bail out early. On his way to the train, the man meets the actual girl he was thinking of (both women have the same given name) who is just as pretty and likeable as he remembers... and is happily married with several children who made her late for the reunion. He returns home somewhat heartened and determined to make his own marriage work.
- Patlabor: In The New Files, it's revealed that Kumagami once had a relationship with Richard Wong. This naturally leads to a confrontation between the exes, just before he makes his escape. Wong trolls her by pretending to give himself up, because of his feelings for her. She falls for it, he scoops up her up, then... dumps her in a laundry basket and runs off. Needless to say, Kumagami considers them DONE.
- A chapter of High School Girls has Takahashi going to her grade school reunion only to find that her old crush has grown fat, ugly and arrogant.
- One chapter of Sayonara, Zetsubou-Sensei shows two women who'd fought over a guy in high school. He turns out to have become a hugely overweight slob and they reconcile.
- Queen's Blade: Echidna and Irma once had a relationship, during the time Echidna was Irma's mentor. But, for reasons unknown, Echidna abandoned her without a word of explanation, or even a goodbye. When she showed up again, years later, thinking she could pick up where she left off, Irma let her know—in no uncertain terms—that that ship had sailed.
- Highschool of the Dead: Saya used to have a crush on Takashi, when they were kids, and it's implied that she might've still had feelings for him at the beginning of the manga. But she moves on and eventually settles into a platonic relationship with him as she grows closer to Hirano.
- In the 9th volume of Super Gals, Yuuya realises that he no longer has a crush on Ran when he saw her enjoying herself with her boyfriend and felt no jealousy. In a similar vein, he finally realises that the girl he cares about is Mami.
- Subverted in Safety Not Guaranteed: Jeff spots his old high school sweetheart, whom he has not seen in many years. Upon first glance, he is disappointed to realize that she has aged as much as he has in the intervening years and is no longer the teenage girl he remembers. He decides to leave without talking to her, but after some prodding, he eventually meets her and quickly falls back in love with her.
- In Romy and Michele's High School Reunion, Romy did have a thing for Jerk Jock Billy, but at the titular reunion, it's clear that he's gone full Future Loser (fat, slobby, drunk, nails drywall for a living, married to a horrible woman who cheats on him). Admittedly Romy did not harbor any hopes of picking up with him (their last encounter years ago involved him humiliating her terribly), but he thinks he's got a chance. Naturally, Romy gets some late revenge by pulling the same trick on him.
- In P. G. Wodehouse's A Damsel In Distress, Maud meets her beloved Geoffrey—who's turned fat and obsessed with food, and her heart is breaking at the thought she has pledged herself to him, when he gets a break of promise suit served on him. She goes off to find the man who helped her meet him and propose marriage.
- In Dorothy L. Sayers' Gaudy Night, Harriet Vane goes to Gaudy Night to meet an old school friend. Within minutes, they are making painfully polite inquires about the other's life, and Harriet is thinking it's terrible, and she should never have come.
- In L. M. Montgomery's A Tangled Web, used twice.
- Jocelyn left her husband on her wedding night because she had fallen in Love at First Sight with the best man. When he returns and is not the stuff of romantic dreams, she reconciles with her husband.
- When Noel has jilted Gay to take up with Nan, and Nan has jilted him in turn, he comes back to Gay. She realizes how false he is, and laughs.
- Eva Ibbotson's Dial-a-Ghost has the son of the ghost family portrayed with a long term crush on a Cynthia Harbottle. When she turns up as a ghost in the final chapter, she is old, plump and selfish.
- In Edgar Rice Burroughs's Fighting Man of Mars, Tan Hadron has this twice: the first time, he convinces himself that the woman is just dispirited from her captivity, but the second time, he realizes the truth and repulses her.
- In John Hemry's The Lost Fleet series, an old love of Captain Desjani is one of the prisoners they rescue. Desjani soon realizes that he changed in the prison camp, and he starts to have an affair with a subordinate, for which he was transfered.
- In Dreadnaught, Rione has more than a touch of this with her husband, long a prisoner of war.
- In Michael Flynn's The January Dancer, Hugh finds that Fire Forged Friendship faded over time, and one such friend resents his return.
- In P. G. Wodehouse's Jill The Reckless, Jill had deliberately thrown herself into work, far from Derek, to recover from him, and just before the meeting, noted that it had worked. Nevertheless, meeting him again reinforced that.
- In Robert A. Heinlein's If This Goes On —, John's "Dear John" Letter inspires brief agony before Maggie asks him to remember the girl, and he realizes that she had not impressed herself on his memory.
- In Nick Hornby's High Fidelity the main character has never really got over Charlie, the girl that broke up with him at university. When he meets up with her again years later, it takes a few hours for him to come to the conclusion that "Charlie's awful".
- In Katherine Paterson's Of Nightingales That Weep, at the end of the novel, Takiko's ugliness from hard work outside instantly repels a man who had been attracted to her beauty.
Live Action TV
- How I Met Your Mother: After years of searching, Ted found the "Slutty Pumpkin," a girl he fell in love with at a party but he never saw again. Both Ted and the girl found the relationship awkward, but neither wanted to break it off because they thought the other person was into the relationship.
- Friends: Monica's situation, when she runs into her Richard after a painful break up several years before. Her boyfriend Chandler, freaks out, thinking she's still crazy about Richard, but Monica's first reaction is that she feels nothing for Richard anymore and there are No Sparks. (Of course convincing Chandler of this, is a whole other mission.)
- Shameless (US version): Fiona starts flirting with the guy she had a crush on in high school, but once the have a very awkward sexual encounter Fiona doesn't feel the same anymore.
- This happens for Scully in The X-Files in episode "all things". In medical school, she had an affair with a professor. Once she found out he was married, she was horrified and left her medical career to join the FBI. Ten years later, she runs into this professor, who is in the hospital for a heart condition. She is understandably perplexed as to why he's in Washington D.C., and he explains that his wife is now dead and he's come to invite her to run away with him. However, Scully is now ten years older, wiser, and has a life of her own now. It's an episode that is a major reality check for Scully about where her life has gone and what it could have been. In the end, she turns down the offer and realizes she likes the way her life has turned out. This also marks the start of Mulder and Scully's sexual relationship. Probably.
- An episode of Frasier where Woody from Cheers shows up has this happen to Frasier. While he enjoys the first night that the two hang out, when he and Woody start spending more time with each other he quickly realises that they've grown apart and have very little in common aside from their past connection to Cheers, but can't bring himself to hurt Woody's feelings by revealing this. Ironically, it turns out that Woody was experiencing the exact same thing from his perspective but couldn't bring himself to hurt Frasier's feelings about it. Once the misunderstanding's cleared up, the two part ways amicably agreeing to hang out for one night only in another ten years or so.
- Garth Brooks:
- "Every Time That It Rains" tells of a romantic encounter between the narrator and a waitress. They try to go for a second date but it's just not the same and they decide to be just friends.
- In "Unanswered Prayers," he meets his high-school crush years later, after he's married, and realizes that he's glad he didn't end up with her.