You Were Experienced, I Wasn't, And This is How We Started Dating

[Ojisama]

The series centres on the relationship between Ryūto Kashima, a gloomy social outcast, and Runa Shirakawa, a popular girl at school. Their relationship begins when Ryūto 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.