Yume de Aetara

夢で逢えたら (1999)

Yume de Aetara is a story about one guy Fuguno Masuo (a complete loser when it comes to relationship with women) and two girls: Shiozaki Nagisa and Hamaoka Miho. Since the story is pretty simple (and hilariously funny), further explanation will spoil everything (take the hint: watch it yourself!)

(Source: AniDB)