I played this short part of the game you made and it was rather interesting! Therefore, even if it's a very small part, I'll try to make some kind of review.
I really like are the graphics, they look simple and clean. It's a pleasure to look at them (and at the awesome clothing) so I hope you won't completely change the sprites and backgrounds.
The vast choice of dateable characters is nice too, but it would be a shame to neglect some of them, as I've seen in other games, because of this. :(
Now, about the main character...
He changed his expressions mostly while talking to others (and I think it still wasn't enough, haha), I don't understand why you didn't change them to match his thoughts as well. It was pretty disturbing to see him smile sheepishly while the situation would've suggest another kind of reaction.
About his personality, I think that sometimes he is way too naive.
Anyway, good luck with your game!