Episode 3 of "My Tiny Senpai" begins with Akina at the office, once again trying to play matchmaker for Shinozaki. He talks with Shinozaki and recalls how excited Shiori was when he started working under her.

The episode then transitions into a flashback, where we see the differing perspectives of Shiori and Shinozaki. From Shinozaki's point of view, he believes Shiori is closely watching him to point out any mistakes he might make. From Shiori's perspective, however, she is delighted to have someone working under her and wants to support him as best as she can.

On their way back to the office, Shiori and Shinozaki come across a crane game filled with stuffed animals. Both of them notice two teddy bears in the game that remind them of each other. Since Shiori is so excited, Shinozaki decides to win the teddy bears for her. Though he fails in his first two attempts, he succeeds on his third try, winning two teddy bears of each kind. He gives them to Shiori, who is overjoyed.

Back at work, their supervisor tasks them with developing ideas for a dating website. However, since neither of them has ever been in a relationship before, they struggle to contribute anything substantial.