The Night is Short, Walk on Girl Yoru wa Mijikashi Arukeyo Otome English Subbed

A black haired girl is walking around the streets of Kyoto, from the night scene of Pontocho to a second-hand book fair in Shimogamo, then off to a college fair. The main character that has a romantic feeling for her secretly follows her around and looks for the opportunities to run into her in a manner that seems like a coincidence. Unfortunately for him, she is not interested in love yet, so she does not notice his feelings. What awaits these two characters are a series of crazy incidents caused by bizarre individuals, such as a person who introduces himself as Tengu, the god of second-hand books, or a money lender, who collects young men’s underwear and lives on a three story barge.

(Source: Sugoi Japan, edited)