In the 2nd Generation, you can meet each of the candidates for Romance consecutively to view the Cherry Blossoms on the occasion of the Flower Festival. I believe this may explain the odd anomaly in the 1st Generation whereby your character could ask three girls in succession to view the blossoms with him, but then could ask no others after that.
Here is the Event with each of the 'bachelors' and the dialogues of the girls:
As in the 1st Generation, speaking to every one on the day of any Festival raises heart levels. Speaking to any candidate for Romance raised both Love and Friendship levels.