WARNING: The following contains spoilers for Episode 7 of My Senpai Is Annoying, "Everyone's Holidays," now streaming on Funimation.
My Senpai Is Annoying's romantic office hijinks continue in the summer, and while Futaba and Harumi hang out together during Golden Week, Kazama Sato comes to realize if he doesn't make his move now, he will never get another chance. He has his eye on the lovely Toko Sakurai, but as a meek kuudere, he cannot easily express these amorous feelings.
Kazama has made some token progress with Sakurai so far, including on Valentine's Day, but it's not enough to make them a real couple, and Kazama knows it. Now, during Golden Week, Kazama gets his best -- and probably last -- chance to score a real date with Sakurai.
In the office, Kazama sees Sakurai chatting happily with some other men, with a few getting serious about making a move on her. The others mean well, and Kazama trusts them around Sakurai, but his personal interests are more personal than that. He began My Senpai Is Annoying as a modest and quiet fellow, but by Episode 7, his strong feelings compel him to marshal his courage and make a bold move to get on Sakurai's radar as a potential boyfriend. Time is running out, so Kazama takes the plunge and invites her on a date with him. She agrees.
Kazama and Sakurai meet at the appointed place early and depart for the aquarium, a classic date venue in anime. Along the way, they score a couple's discount when buying tickets, and Kazama hesitates before Sakurai tells the employee they are a real couple. They watch dolphins perform -- including a kuudere dolphin inexplicably named Sota-kun -- while the human Sota buys Sakurai a stuffed plushie of Sota-kun as a gift. He doesn't yet have the courage to give it to her though, and hasn't yet made a big romantic gesture of any kind. So far their date is platonic, at least where Kazama is concerned. At this rate, he and Sakurai might end the day as just friends, and she will see no reason to turn away other suitors for Kazama's sake.
Into the early evening, Kazama continues his date with Sakurai as though on autopilot, though Sakurai doesn't seem impatient with his lack of initiative. She may be empathetic to his timid ways, possibly knowing he struggles with some private insecurities of his own. Kazama is used to being a shy gamer geek who never attracts the attention of women, and may feel in over his head here. That's when a couple of punks harass Sakurai, and Kazama finally re-enacts a heroic RPG character defending his female party member, as he always intended to.
He helps Sakurai shake off the punks and get away, then finds the courage to share the Sota-kun plushie -- and Sakurai loves it. She also compliments Kazama for delivering a cheesy but impressive line to scare off the punks, something Kazama tells her he learned from a shojo manga series.
The date ends well and overall, Kazama's romance story arc is resembling Futaba's more than ever. He may be a kuudere rather than a proud tsundere like Futaba, but they both have insecurities getting in the way of their amorous feelings and generous hearts. Yet bit by bit, both find the courage to overcome those obstacles and pursue true happiness. The romantic underdogs have finally found their inner strength, and for My Senpai Is Annoying's Futaba and Kazama, there's no going back.