If you liked the The Kabocha Wine anime, the Anime-Planet community thinks you'd like:
Fifteen-year-old Kasumi Kishimoto has a boyfriend overseas and high hopes for her future: she’s been accepted to Myoujou High School, and is moving to her aunt’s house to live. But little did she know that she’d be sharing her home with not one, but four boys! Perverted and playboy Shin, hungry Takashi, bizarre Makoto and endearing Yusaku help make Kasumi’s life more interesting; and in the midst of classes, baseball games, and dealing with the school’s all-male Cheer Squad, there are plenty of fun times to be had at Myoujou High.
These titles are two older romantic comedies that have a very similar old school 'school life' setting. Just trust me that if you liked one, you'd surely appreciate the other.
Both old school Anime in a sense of seeking out love, and deep meaningful relationships. Despite minor differences in terms of story, and they are subtle, you'll enjoy both with great pleasure. Especially if you're into old school anime.
Lovely Complex is a story of a boy and a girl. The girl, Koizumi Risa, is much taller than the average Japanese girl; and the boy, Atsushi Otani, is much shorter than the average Japanese boy. Due to their immense difference in size and constant bickering with each other, the duo is unwillingly the school’s comic relief. As Risa and Otani continue to provide endless laughter for the masses, their friendship develops; and with that, so does Risa’s feelings for Otani...
Both anime feature a couple with huge height disproportion. In both the female lead is huge and the male lead is short. If you were looking for anime with such theme, then those two should suit your taste.