Understanding is one of the six side stories included in Doki Doki Literature Club Plus!. This side story includes two parts that focus on Sayori and Yuri in a separate timeline to Doki Doki Literature Club!. Completing a side story each unlocks a new artwork in the gallery.
Understanding starts with Yuri joining the Literature Club. Yuri is immediately forthcoming with books, bringing two large books to the club and asking whether any of the members liked fantasy. Sayori joins Yuri at her desk, asking if they could get to know each other first, while Monika focuses on the administrative aspects of the club. Yuri states that her intention to join the club was to find like-minded readers, reflecting that she found it through her previous interaction with Monika in the side story Trust. She reveals that she had taken a few days to build to courage to join the club, worried that she came across as too inconsiderate to Monika in their interaction, and hints at her own personal struggles with overthinking. The two continue with their small talk, with Sayori revealing she is into arts and crafts and Yuri showing she likes nature, and Monika officially appointing Sayori as Vice President if it hadn't already been implied. The day draws to a close, with Yuri leaving first. Sayori and Monika discuss their plans for the next day, with Sayori offering to join Yuri with her reading.
On the following day, Monika is busy preparing posters, leaving just Yuri to join Sayori in the clubroom. Yuri immediately apologizes to Sayori, who is left confused, as Yuri changes her mind on reading, feeling as if she came across too overbearing. Sayori insists that she wants to join Yuri with reading, expressing that it's something fun they could do together, alleviating Yuri's fears of dragging Sayori into something she didn't want to do. The two members begin reading, with Sayori asking questions along the way, trying to wrap her head around the story. At the end of the day, the two finish the chapter and Yuri asks Sayori what she thought of it. Sayori responds, somewhat avoiding the question, stating that she enjoys seeing Yuri happy and that she'll keep trying her best to read. Yuri gets the impression that Sayori wasn't really interested in her books, confirming her fears that she had in fact dragged Sayori into an activity she didn't like. She expresses that she wants to do something else the next day, and quickly leaves the clubroom, avoiding much confrontation. Sayori, wracked with guilt for making Yuri uncomfortable, blames herself for not being able to follow along with the story well enough and continues to read the book alone.
Day three opens with Sayori in the clubroom by herself, wrestling with her own thoughts from the previous day, hoping that Yuri at least returns to the club. Monika, who is late to the session, finds Yuri waiting outside the clubroom on her own, while also noticing that Sayori is inside. Sensing some potential conflict, Monika invites Yuri to join her on a walk. The two discuss the previous day, with Monika enquiring how she got on with Sayori. Yuri reveals that Sayori wasn't into the book, and that she feels bad for forcing her own interests over Sayori's. She expresses her own inabilities in social situations, that she feels like Sayori is taking pity on her too much. She would rather Sayori simply admit she's not into her interests, rather than being too nice her and inconveniencing herself just to help make Yuri feel more comfortable. Monika replies, saying she should explain her thoughts directly to Sayori, and shares that Sayori enjoys going out of her way to make the other person happy, much to Yuri's dismay. The two eventually return to the clubroom door having photocopied new fliers, and Yuri builds up courage to enter the clubroom on her own.
Upon entering the clubroom, she realizes what Sayori had been doing the whole time. Sayori proudly presents all her work to her, however much to her surprise, Yuri despairs. She opens up to Sayori, explicitly stating that she has accepted her own social struggles and that she doesn't want Sayori to cater for her. Sayori tries to reassure Yuri, however Yuri responds coarsely, stating she does not 'want her pity'. Yuri, overwhelmed with guilt after realizing her own violent outburst, apologetically collapses to her knees, looking away from Sayori and beginning to cry as she fails to articulate her own thoughts. Sayori pulls Yuri into a tight embrace from behind, pictured in a CG for the player, and gives Yuri time to speak her mind. After some thought, Yuri speaks up and explains that she's gotten used to others not liking her, and that she struggles to accept gratitude from others as she generally sees the negative side of things. She reveals that she joined the Literature Club as she thought of it of a place to learn to get along with people, and to hopefully break her social anxiety; so that she can discuss her books without feeling like she is being too overly obsessive and dragging others into a conversation they don't want to be in. Sayori thanks her for her openness, and reiterates that no matter what Yuri thinks, Sayori already likes her for the person she is. She admits that she is not used to reading, but reassures Yuri that she is enjoying reading her books and wants to understand why she likes it so much, not out of pity for her.
With this mutual understanding of each others' needs, the two return to reading feeling much more relaxed. Monika returns to the clubroom, and Yuri offers to return Sayori's gratitude by asking her to teach her poetry instead, concluding the side story.