Kaguya-sama: Love Is War (2019)

S2E7 Kaguya Wants to Undress Him / Kaguya Wants to Make Him Let Go / Miyuki Shirogane Wants to Make Her Read / Kaguya ♡ Aquarium

Ishigami expresses his strong belief that "guys who wear boxers are just man whores." Taking his comment to heart, Kaguya becomes curious about what kind of underwear Shirogane has on. She brainstorms various clever ways to sneak a glimpse, but all her plans turn out to be too risqué. Ultimately, she decides to directly ask him about his underwear preferences. However, Shirogane misinterprets her question, thinking she wants to know about his lingerie tastes. This leads him to daydream about the types of underwear he wishes Kaguya would wear.