If I See You in my Dreams(1998)

If I See You in My Dreams is a romantic comedy series following Fuguno Masuo, a 24-year-old virgin hopelessly devoted to Shiozaki Nagisa, a kindergarten teacher two years his junior. Though popular with women, Masuo has eyes only for Nagisa. His clumsiness and thick-headedness constantly land him in awkward situations that Nagisa inevitably misinterprets, creating comedy from misunderstanding and miscommunication. As Masuo fumbles through his pursuit, the series explores whether genuine affection can overcome his own bumbling nature and the obstacles he unwittingly creates. The show balances humor with the earnestness of unrequited love, capturing the frustration of wanting someone while being your own worst enemy.