@viovee
The novel didn't give more info about the first timeline than this manwha. The casino backfire to Asher and make him look like incompetent. He was threaten from the aristocrat faction to marry Isis and was tied most of the time.
@uncoolist
No they didn't confess each other.
In love Aria is slow, she never love or be loved in the first timeline so she confused because she don't understand herself but the feeling isn't so bad so she don't think to much about it and let it go. (If you are an observer, she do the same thing with Sarah)
Asher like her, since he meet Aria his situation change and he can now fight the aristocrat faction. He is confident in his feeling that why he act this way.
@Wyrm
The story follow most of the time Aria perspective, she see well that Mielle is incompetent but not the other characters.