This Syaoran Li is specifically referring to the sequel series of the original Cardcaptor Sakura anime. While the first series saw Li playing the traditional role of the friend yearning to be something more, Clear Card-Hen managed to provide fans with the relief they had been looking for. After Li returns following his departure at the end of the previous series, he and Sakura promptly profess their feelings and become a couple.

Li falls at the bottom of this list due to his luck in securing Sakura. While Li is undoubtedly Sakura’s childhood friend entering into Clear Card-Hen, he does not accomplish what the traditional childhood friend is most noteworthy for. This being; failing miserably! Li is an honorable mention in a world of rejection as to the possibility that a childhood friend may one day emerge victoriously. Perhaps, he was the inspiration for Shida Kuroha all along.

This anime is a rollercoaster of feels and Nanami’s journey is no exception. Being the stern disciplinarian that she is, it’s evident that her confession would take some time. Nanami is not one to let herself be vulnerable, especially when she comes to learn of Kanda’s feelings for Mashiro. However, with the school year coming to a close and the students moving in different directions, she needs to get some feelings off her chest.

However, when the time finally comes, she chooses to sacrifice her own feelings to encourage the person she loves. After watching several other rejections throughout Sakura-so both professional and emotional (Misaki’s confession to Jin or Kanda’s game rejection for example), Nanami’s rejection was akin to pouring salt in our already gaping wound.

Seemingly forced to follow Noir in whatever new pastime takes his fancy, Emma is the childhood friend who just won’t quit. After losing his job at the library where they both worked, Emma resigned to follow Noir into the Hero’s Academy. There, she continued to try with all her might to get closer to him, by joining the Odin Adventurer Guild. Despite her cute demeanor making her very popular with any guy who meets her, it seems she only has eyes for Noir and is willing to undertake any new profession to see that love ratified.

Resigned to the fact Noir needs a harem to live, she allows herself to be toyed with and kissed in helping him gain power. Even going so far as to refuse a breast reduction spell to appease Noir’s tastes (meaning her back is in constant pain) it’s clear that Emma is one childhood friend who is in the love war until the bitter end.

Hanekawa receives the award for the most brutal rejection on this list. Having been secretly in love with Araragi over the years (on top of her copious levels of stress) it one day becomes too much to bear. This is where we see the birth of Black Hanekawa; the incarnation of all Hanekawa’s repressive thoughts brought to life in the form of a cute cat-girl. Wanting nothing more than to free Hanekawa from her personal hell, Black Hanekawa reeks rampage on the city to blow off steam for regular Hanekawa. Ultimately, Araragi is forced to intervene and, luckily, manages to save the day. Having regained her senses, Hanekawa confesses her feelings but Araragi (currently dating Senjougahara) rejects her.

The Monogatari series as a whole does what no other harem anime dares to do. It places its protagonist into a relationship from the third episode. This means that, surely, there is no hope for any other love interests. While they certainly try to tempt Araragi away from his beloved, he remains steadfast. After all, being a boyfriend is a 24-7 gig no matter who may offer themselves unto you. Hanekawa shows real courage in this anime. In a world where childhood friends roll over and die to allow their crush to be happy, Hanekawa actively tries to chase after the man she wants. Sure, she is not successful, but at least she gave it her all. Now, a world of endless possibilities awaits her, as she will not be held down by thoughts of what could have been.

Perhaps the poster child for tragic childhood love stories, here we have Onodera. Usually, in romance anime, it is fairly obvious who the protagonist will wind up with. The childhood friend, in these scenarios, is given little to no screentime when compared with the main love interest, and so with each passing episode, more hope is lost that they will be chosen. However, when it comes to Nisekoi, fans were beside themselves when confronted with arguments defending Chitoge. People would defend Onodera to death despite Chitoge being the main love interest.

While the anime of Nisekoi has since concluded with no signs currently of a follow-up, fans were forced to storm the manga stores in hopes of uncovering the truth. Unfortunately, after reading the final chapter, these fans were scorned again as Onodera failed to snag Raku. Onodera amassed a cult following over the series as, unlike Chitoge, she was always very sweet and understanding. Chitoge rubbed some fans the wrong way with her over aggression and unwillingness to admit fault. Onodera was always likable and it was very disheartening to see her trip at the final hurdle.