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* Kouichi's ADV Events are often as not downright heartbreaking, especially "Family~Kou," which shows the aftermath of the TakingTheHeat incident from Kou's point of view. His father has to pick him up from the police station; they go back to West Beach and have an awkward, mostly silent cup of coffee. Before leaving, his father tells him that they've found a buyer for the property, and the brothers won't be able to live there any more.
-->''I crawled into my bed and covered myself with a blanket, and then I cried for a while.''
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* There are a lot of references to the Sakurai brothers' PerpetualPoverty. Sometimes it's played for laughs, but then there are moments like Kouichi muttering to himself that he should have skipped lunch when the protagonist suggests they stop for tea after school, or the fact that (with one exception) all of the gifts Kou gives the protagonist are ''his own belongings''. When she receives his gift from the third-year Christmas party's gift exchange, a vintage LP record, the protagonist even thinks to herself that "this is someone's treasure."
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[[folder:Tokimeki Memorial: Girl's Side 1]]

* Most of the end-of-game {{Love Confession}}s are normally pure heartwarming, but Shiki Mihara's has more of the flavor of an AnguishedDeclarationOfLove, as he miserably confesses to the heroine that he hasn't been able to paint and can't bear the thought of losing her. [[VideogameCrueltyPotential To make matters worse]], it's possible for the heroine to tell him she doesn't think she's good enough for him, causing him to plead desperately with her to believe that he loves her.
* When riding the ferris wheel with Kijyou Madoka in winter, there's a scene where he tells you of a good memory he has of his parents, riding a ferris wheel years ago. Since his mother is dead and it's revealed that he is on pretty shakey grounds with his father and living on his own due to that... hearing of one good memory, one that sounds like it's a pretty old one, tugs at your heartstrings.

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[[folder:Tokimeki Memorial: Girl's Side 2]]

* In Teru's route, nearly-constant references to Sangosho in his dialogue make it clear that the cafe is important to him; his ambition is to take over ownership of it someday. So during his third-year Christmas event, when the heroine visits him because he missed the Christmas party and learns that the cafe is closing - and Teru, uncharacteristically subdued, asks if she'll let him put his head in her lap for a little while - it tugs at the heartstrings.
** The real tearjerker of Teru's route, however, comes the following month, when he calls the heroine out to the beach and tells her he's moving away and has given up on his dream of running Sangosho. When the heroine says that isn't like him quickly gets angry and demands to know what she really knows about him, [[CruelToBeKind telling her that the way he's behaved toward her has all been a lie]] and she should just forget about him, and it's painfully clear [[IWantMyBelovedToBeHappy why he's doing it]], and it ''stings''.

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[[folder:Tokimeki Memorial: Girl's Side 3]]

* Ruka's accident. After telling the heroine that he'll end all the fights for her sake, he crashes his bike and wakes up just when the heroine arrives to the hospital, and tells her that he wouldn't have minded if he had died there.

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