Keikenzumi na Kimi to, Keiken Zero na Ore ga, Otsukiai suru Hanashi.

Our Dating Story: The Experienced You and The Inexperienced Me

Ryuuto Kashima is the school’s gloomy introvert, and he’s got a crush on Runa Shirakawa, the popular girl. After losing a bet to classmates, he confesses his feelings to Runa one day. Shocked and secretly just as inexperienced as Ryuuto, Runa agrees to date him. The relationship grows between two people who are as similar as they are different. Will their young love blossom? Time will tell! (Source: Crunchyroll)