
Really it seems she was really sad that the mother died... maybe she didn’t know.....
Is that why her hair color is the only one different?!
But doesn’t he want to marry her family for her family support does it matter if she was illegitimate child or not she still carry her dad bloodline, and is considered an accepted daughter so it didn’t matter if she was the daughter of his main wife or another women right? He just needed her family support.

The person who ripped the chapters from another site forgot to upload chapter 1, the chapter 1 right now is just the prolouge.
So basically, the grandfather fell in love with the mother as she was a beauty, but was unable to pursue her because she was already engaged
He still kept in touch with the family and they promised to marry their firstborns. The grandfather is sure that the Duke must marry "Hailey", a child who resembled their mother's beauty, however Hailey is actually a son. And Emily has the closest resemblance after him, and is also a woman.

People have already explained it to you, but in case you're also interested in reading the chapter then you can check out m-an-ga-dex (erase the -). I can't drop the link or even type out the full name of the website because mangago deletes it automatically lol. But if you google it and search the title of the webtoon, you'll find the first chapter (translated).
Why is he so set on the younger sister Emily? He came there to marry someone from their family..... usually it would be the eldest daughter but he immediately chose Emily..... he doesn’t like Emily at the moment so that cant be the reason... and he isn’t the type of person to chose someone because of looks....
In the OG it said they fell in love and it was because he was courting her but again why did he skip over Dylan.