|"The Cupid Karuizawa"|
|Author||Shōgo Kinugasa (Story)
|Available in||Light Novel Volume 7.5 (Melon Books' Privilege-only)|
|Release Date||January 25, 2018 (JP)|
|Next||"Conflict of the Mind"|
Due to a request by Maya Satō, Kei Karuizawa carries out the request to be a cupid — one who tries to get others along; by forming a double date between Kiyotaka Ayanokōji, Maya Satō, Hirata Yōsuke, and herself on Christmas Day.
As they were on the double date, the first attempt by Kei involved her calling out both Kiyotaka, and Maya as looking like a couple. Maya flirtingly responded by restating what Kei said, but the outcome was not found to be too sincere. Kiyotaka answered in his usual, disinterested manner by vaguely agreeing to the idea of looking like a couple. This led to Kei feeling displeased with Kiyotaka's response, and started to backtrack with dark thoughts, but quickly regained consciousness with the idea that she needs to fulfill her role as the cupid.
Kei moved on to her next attempt which was to question about Maya and Kiyotaka's relationship status in a persuasive manner. Maya then eagerly started to deny the claim from Kei, but Kiyotaka was still found to be disinterested with a serious look on his face, extremely displeasing Kei.
Kei's cupid methods were found to be ineffective to Kiyotaka as any of her words did not seem to reach him emotionally. Forcefully, this led to Kei's last plan which was to depart from Kiyotaka, and Maya, and allow for them to have alone time; Kei was also eavesdropping them from the distance. Unfortunately, the conversation between the two appeared to be awkward, and silent.
Even though Kei's love methods were ineffective, she still shows hope as she plans to hit Kiyotaka with the love arrow one day.