Our Dating Story: The Experienced You and The Inexperienced Me

The story centers on the relationship between Ryuuto Kashima, a gloomy social outcast, and Runa Shirakawa, a popular girl at school. Their relationship begins when Ryuuto has to ask Runa out as part of losing a game, and she ends up going out with him after saying "Well, I'm free right now, after all." They have completely different social circles, and completely different hobbies, but as they hang out with each other, they begin recognizing and even accepting those differences as something to bond over.

(Source: Anime News Network, edited)