Mezon Ikkoku (TV series 1986-1988)

Yusaku Godai, a bumbling college student, is in love with his landlord, Kyoko Otonashi. Otonashi, while attracted to Godai, is hesitant, having lost her first husband in the not-too-distant past. The rest is history: Godai schemes to win Otonashi's heart, all the while battling off his rival, Shun Mitaka, and fending off his lunatic neighbors, who include an old woman who lives on gossip and liquor (Ichinose), a scantily-clad flirt (Akemi), and a bizarre, enigmatic man (Yotsuya). - IMDb