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General
- Despite being a usually lighthearted fic, it does have its sad moments here and there for various reasons, such as one of the girls dealing with a recent break-up or unrequited love, which leaves them a little hard to open up to at the beginning.
- Sam's initial inability to move on from Danny always leads to heartbreak, especially when her jealousy nearly destroys her friendship with him and Team Phantom. Even after they patch things up, Sam is forced to accept that Danny doesn't reciprocate her feelings for him.
The Many Dates Of Danny Fenton
Danny telling Katie off!
- Danny's lashing out at Katie when she ends up hurting her little brother. While it was an accident, Katie is horrified at what she's done. Even moreso when Danny outright says he doesn't like her and never wanted to be with her, much less be kissed or cuddled by her. Having spent the entire time thinking Danny returned her feelings, Katie is heartbroken.
- Katie's reaction to learning that she not only injured her brother, but also terrifies her family and that the guy she has fallen in love with can't stand her is truly heartwrenching. It's been stated that Katie hardly remembers what she does during her rampages but when forced to see the consequences of her actions, you can see how sad, horrified and ashamed she feels.
- Even the Warner Siblings, who usually just joke around, aren't making light of the situation.
Danny and Kara
- Kara being reminded of her parents and the fate of Krypton. Even if she doesn't give them the details, she explains that her folks are no longer around, which makes even the usually cheerful Fenton parents somber.
- Sam, after being caught and confessing her feelings for Danny, gets rejected by him for Kara and he ends their friendship since she broke the trust he had in her. Even if she brought it on herself, it's still rather heartbreaking.
Danny and Kim
- Unlike Vicky, Cree's arrest falls under this. While she's lucky by only getting five years in prison, Cree is forced to live with the knowledge that everything she did was all in the name of some stupid game by two deities. She even tells Danny that she thinks she should have gotten a longer sentence.
Danny and Gwen
- Of all the 'Danny rejects Sam' scenes in the series, this one is arguably the most painful. To wit, as an unintended consequence of Sam's stalking, Ben wasn't able to give Danielle a cure to her condition and Gwen is effectively banished from Amity Park. As a result, when Danny, Tucker, and Jazz confront her, they give Sam a scathing "The Reason You Suck" Speech and kick her out of Team Phantom.
Danny and Makoto
- Minako, as Sailor Venus, being turned down by Danny Phantom. At the time she met him, she was unaware he was the same boy Makoto had fallen for. And so, after spending most of her time around him hitting on him, right when she's about to kiss him, he quickly informs her he has a girlfriend and was unable to get a word in edgewise due to her flirting and ghosts attacking. Although Minako accepts this and commends Danny being loyal to his girlfriend, unaware who it is at the time, she's clearly heartbroken. Unlike the scenario with Katie, Danny is genuinely sympathetic to Minako and wishes he knew someone she could meet. The narration implies that had he met her before Makoto, he might have been more accepting of her advances.
Danny and Kitty
- Danny and Katie's meeting post-main story is pretty sad. Katie had come to Xavier's school in hopes of learning to control her powers and have another chance with Danny, only to see that he's in a relationship with her classmate, Kitty Pryde. Katie can barely keep it together until she makes it to the danger room and once safely in there, goes on a heartbroken rampage.
- Later on in the story, Katie snaps at Danny, calling him a coward. She points out that while she did have issues controlling her powers and temper, which made her dangerous, he only made things worse for both of them by pretending that he liked her to appease her. Which not only caused Katie to pursue him to his own discomfort, but also prevented her from finding someone that actually liked her and would have spared her heartbreak. Katie also points out that had Danny talked to her about her temper earlier and told her about Xavier's school, then she could have gone there before the carnival incident and her brother wouldn't have gotten hurt. Danny has a moment of genuine guilt for the way he treated Katie up 'til that point and admits he screwed up. Even the Warners agree that she made some good points and that whole display was depressing.
- It also says something that Katie still feels guilty over what she did to her brother. She tells Danny that she hopes her brother never finds out what a coward he really is before storming out. Pretty sad to watch considering how crazy she was for him before then.
- Danny also feels guilty upon Katie pointing out that him getting together with Kitty, who goes to her school, and them hanging out at Xavier's with Kitty being unaware of their past relationship only made her feel worse.
Danny and Wendy
- Danny ends his friendship with Sam after learning how she stalked him and Wendy out of jealousy. Just like in the main sequel, Danny was hurt by her betrayal and Sam is heartbroken as a result.
