Thanks to interference from Yukino’s mom, Yukino and Yui’s plans for a Soubu High prom face ruin. But Hachiman has an idea: What if he were to devise a fake prom plan to make the girls’ version look better and disguise his scam as a genuine proposal? Of course, there’s no guarantee this delightfully devilish scheme will work, which is why Hachiman will need all the help he can get...

Hachiman Hikigaya is a cynic. He believes "youth" is a crock-a sucker's game, an illusion woven from failure and hypocrisy. Unsurprisingly, he's not the most popular guy. Meanwhile, there's Yukino Yukinoshita-brilliant, beautiful, and chillier than winter in Antarctica. Would you believe she's not exactly beloved by her classmates either? The unlikely pair gets forced into a club dedicated to helping solve their fellow students' problems. But will an ice queen and a screwup really be able to help anybody?

Planning for the Soubu High prom continues, and Yukino is steadfast about working without Hachiman and Yui. But when she receives complaints from parents worried about moral impropriety, it might just put the kibosh on everything. Even worse-the parents’ representative is Yukino’s mother, whose disarming social grace makes negotiating all but futile! Can Hachiman help without going back on his word to Yukino? And as he spends more time with Yui, where will his feelings take him?

As Valentine’s Day approaches, Yumiko is back with another request for the Service Club! She wants to figure out a way to give Hayama some chocolate, but standing in her way is his well-known policy of never accepting gifts on February 14. Hachiman, Yui, and Yukino decide to hold a cooking class as camouflage for some sweet exchanges, but their plan may lead to some unforeseen results-including a reminder of the unspoken feelings among the three of them...

The seasons turn to spring as the story plunges into its final arc! Hachiman and Yui share their thoughts with each other, and Yukino lays bare her own feelings in the form of her "final request." Meanwhile, Isshiki Iroha visits the Service Club with a request to jazz up the school graduation ceremony...with a prom! This time, Yukino wants to handle the job on her own, but things might not go as planned...

Soubu High’s queen bee, Yumiko, has come to the Service Club with a forlorn expression and a request: Find out Hayama’s plans for his educational track. Now it’s up to Hachiman to deduce the truth, and he’s well aware that cracking the flawless facade of the most popular guy in school is no small feat. But the attempt may just lead to some revelations—about Hayama, himself, and the weight of expectations.

Hachiman, Yui, and Yukino are back on the same page (more or less), and now the Service Club can devote its full attention to salvaging the joint Christmas event with Kaihin High School. But even they’re having trouble with the stranglehold Kaihin student president Tamanawa has on the planning, with his endless parade of pointless meetings! Hiratsuka-sensei might hold the key to breaking through, and it’s...tickets to Destiny Land theme park?!