Thank you so much for playing!! I'm sorry if there's confusion, a lot of the game isn't finished and I need to clean up the walkthrough. Also, I slightly regret having two characters named Ashton...
So with Ashton (with yellow eyes) his second date which takes place in the garden isn't done yet, to get that he makes it very easy for you, you choose either his room, which is one date, or the garden, which is another.
Ashton with red eyes however won't make it easy, you just have to be persistent, that is after you've dated him once.
I hope that helps, please let me know if you'd like me to explain it more.