Anime & Manga Asked on October 2, 2021
It’s evident that Yui’s been in love with Hachiman quite early on in the story. I always thought that it started right after her matter with Yumiko’s been solved (I think it was episode 2 of the anime).
But the issue with her cookies for Hachiman in the last episode of season 2 made me doubt it. It’s clear that they’re meant romantically, and it’s been hinted that the ones she gave him in the very first episode were also meant that way, which would mean that Yui loved him since the beginning of the story. Although, I’m not completely sure if I understood it correctly. The cookies in the first episode could have also been just her way to thank him for saving her dog.
Regarding Yukino, it’s very difficult for me to find the moment she started to fall in love with Hachiman ("started" because I believe that she fell in love with him slowly over time) as she doesn’t express her emotions as much as Yui, and for most of the first half of season 2 her relationship with him had been "overshadowed" with their confronting principles (maybe not a good description of what actually happened, but you get the gist of it).
I think Yukino started to love Hachiman shortly after their "dispute" was solved in episode 8 (s2). That is further supported by that picture of herself with Hachiman from the amusement park she’d kept behind her plushie on her bed (see episode 2, s3). Thanks to a Reddit post I’ve realized that the paper sheet Yukino quickly put away after that waterfall scene is most likely that picture.
Maybe another interesting fact: according to a different Reddit post, that plushie was the one Hachiman won for her. Unfortunately, I don’t know if that’s true as I can’t remember having seen it in the anime. Maybe it was depicted in the novel?
But maybe she loved him even before they solved their dispute but there was simply no moment in which she could have expressed it (properly) because of that dispute. Or maybe a reason why Yukino became so upset with him after his fake-confession to Hina was that she cares greatly (and romantically?) for Hachiman and doesn’t want him to get hurt any longer with his methods.
Going further back: at the end of episode 13 (s1), there’s a scene that might hint that Yukino has already started to fall in love with him (she blushed when Yui pointed out that Yukino also watched Hachiman during the sports festival), although it could be also interpreted that she cared for him as a close friend.
Worth mentioning is also Yui’s monologue after finding the picture behind that plushie on Yukino’s bed. If I understood it correctly, she already felt being "the third wheel" for a long time. Maybe that hints that Yukino’s already started to love him in season 1. Or it might be that Yui simply felt their "good chemistry".
A scene that might support the first one is the confession-scene in episode 11 (s3, 18:40+): Hachiman asks Yukino to allow him the privilege of distorting her life. Yukino then tells him that both of their life’s already been distorted from the very beginning and Hachiman further says that it’s only going to get even more distorted.
A Reddit post came to an interesting interpretation: it said that "distorting" here means to become so much involved in the other’s life that it’s being distorted. And the only relationship that could accomplish it is a romantic one. It concluded that Yukino actually said she and Hachiman had been in love "for the longest time" (so likely also since season 1). But does life really only become distorted when a romantic interest (or relationship) is involved and not already with e.g. simple friendship?
When did Yui and especially Yukino (start to) fall in love with Hachiman? If there’s no clear answer to that question from the anime’s perspective, does the Light Novel give an answer to that or at least obvious hints?
It feels like Yukino started falling for him, once she realized that her personality and demeanor didn't affect Hikigaya in the way it usually does with normal people.
In fact, he couldn't care less about how she is, due to the fact that he was forced to join the club to begin with.
Yeah, he was a pessimistic bum who was antisocial, but that time being in that state allowed him to see the hidden nature and flaws of people, along with their tendencies.
This common ground between Hikigaya and Yukino, seeing the bad and ugly in others, and being subject TO that same bad and ugly, formed the basis of their relationship.
Hikigaya was different. Hikigaya was unique. So was Yukino.
They both saw things from the lowest of the low, and when they both realized that they have synergy with how they convey things, the seeds started planting themselves in all the right spots. This was widely apparent throughout the entire series.
Over time, they became comfortable around each other, being able to communicate and mingle in the only way they know how. They didn't receive the same flack they usually receive when they conversed among each other, compared to talking to normal people.
Although, on the surface, their conversations were usually filled with petty banter and the like, people like Yukino and Hikigaya are used to decoding the hidden meanings behind words.
Yukino isn't very good at conveying her feelings, or anything that's on her mind for that matter, which only leaves a few events in the anime that hint at her fondness for Hikigaya.
Their first "outing" in the mall. She was insecure as all hell.
Her displeasure with Hikigaya's solutions to club jobs. She reprimanded him for always throwing himself under the bus.
Her realization that Hikigaya contributes a lot to the club, often relying on him to find a solution to an seemingly unsolvable problem.
Her standing up to Tobe when he publicly talked down to Hikigaya.
Her reluctance to let Hikigaya use his way to solve the presidential election. She didn't want him to be self-destructive again.
Her voluntary discharge of his club membership. She wanted to honor his wishes echoed from when he got into the club in the first place.
The time in the nurse's office when they locked eyes for the first time.
When she kept the photo of them on that water ride next to her bedside pillow.
When she knew Hikigaya would come in and save the prom from being cancelled.
It's very subtle, and coupling Yukino's often reticent demeanor with that subtleness, leaves little to go off of other than what's made obvious.
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Yui is easier to discern. The initial spark was at the very beginning, when she witnessed Hikigaya saving her dog.
Ever since that happened, she's attempted to repay him back for the deed. Once she realized why Hikigaya told her to stop with the act, to free her from feeling indebted to him, she found out that Hikigaya isn't all about doom and gloom.
Another dimension to a seemingly dimensionless character.
She started seeing the other sides of him, and how, despite his outlook on life, he carries on with his solutions, paved the way for Yui to find her own strength to find her own path.
To take control for once, rather than be controlled. To actually feel like she did something for once, without following the flow of others.
Yui didn't think too highly of herself to begin with, that's why she started looking at him. Hikigaya was her role model. She looked up to him. That's why she started liking Hikigaya, for giving her the key she needed to discover herself.
She found herself getting swept away by his resolve to continue onward, quickly becoming entranced by his waltz.
Answered by timex987 on October 2, 2021
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