It was totally worth the multiple playthroughs to unlock all of the romantic endings. However, I do have one major issue to press. There is a difference between "your" and "you're". From the emails I unlocked, you seemed to have neglected to use "you're" in a couple of them where you should have. I only mention this because one of them belonged to Shiro, who is characterized by his preference towards intelligence. To have that kind of simple spelling error in his message just seemed off.
I will give you bonus points for the replay value though. No matter how many times I play the game through, it feels like there are still scenes I haven't read, especially during lunch time. And as there is only so much money you can make/spend, it's a challenge to budget correctly to optimize the amount of item scenes you'll receive in return.
Since I happen to be writing this rather late, please for me for not including more detail. Any spelling mistakes I've made can also be blamed on this reason. I just wanted to inform you that your team has done a very good job putting this together and that you should be proud of your creation. Just have to say though that you kind of made it obvious on who "Alistair" really was. Though Oda's identity was a bit of a surprise. Definitely think the character pairings were accurate once they were properly matched and considered, so excellent job with that.
Anyways, I'll end my little monologue here, so thank you for your time. I hope you continue to make great games as fun as this one.