During the events of despair arc, the real Chiaki Nanami and Gundham Tanaka were both in Class 77-B. Tanaka enjoys playing the video games that Chiaki brings to the class, and is able to grow closer to some of his classmates thanks to her contribution. At the proposal that Nanami should become the class representative, Gundham appears on board with the idea despite his usual indifference towards his classmates and the goings of Hope's Peak.
Chiaki and Gundham share some traits in Despair Arc. Notably, Chiaki tells a story about her 'backstory' that is extremely fantastical and amazes the girls in her class. Moments later, though, she reveals that she was just naming the plots of one of her video games. Gundham exaggerates his upbringing similarly during the franchise, embellishing being 'poisoned' upon a daily basis and being the offspring of an angel and a demon.
During the tragedy at Hopes Peak, it is Chiaki Nanami's execution that plunges Gundham and the rest of his classmates into despair.
During Gundham's reformation in the Neo World Program (Danganronpa 2: Goodbye Despair,) AI Chiaki Nanami patiently helps Gundham to uncover his treasured hellhound earring after he loses it under the floorboards. Chiaki, having been stationed outside, is the only one available to assist him. They did not recover the earring, Gundham having to branch off and uncover it from the floorboards on his own time. However, they did lead to the discovery of the passage way utilized by the chapter one murderer.
Throughout the rest of the game, the two do not speak often, but they are implied to have stayed in the same hotel together with the rest of the students free of the despair disease during chapter three.
After Gundham's execution in chapter four, Chiaki comments on the day's events having been a downer. However, she insists that they continue to try their best, perhaps in honor of Gundham's departing words concerning their need to continue living.
The ship sailed when some fans found Chiaki's dedication to finding Gundham's earring with him endearing. Her patience with him and willingness to play along with his desires, no matter how petty they may have seemed, lead some people to want to see more from the relationship.
Other fans thought Chiaki's embellishments of her backstory in Despair Arc were similar to Gundham's fantastical tales of his life, and thought she could make a good partner for the breeder due to her ability to understand him.
- Gundham and Chiaki were executed sequentially in Danganronpa 2: Goodbye Despair, Gundham having been the chapter four blackened, with Chiaki unknowingly becoming the chapter five blackened following his death.