The douche did not fuck any of the love interest the women he fucks in the story are not in love with the mc and as of the most recent chapter that I know of the mc is only in a relationship with one person that being the fmc. The fmc is never shown to have sex with Ryo in the main story, And she is the one that kicked Ryo in the balls and after that was when Ryo flees the country, as for the dark expression she had that when she found out how much of a douche her boyfriend, best friend was and that he was trying to fuck her boyfriend of couse at the time Ryo thought the mc was a female and when Ryo found out the truth he did not care, and the other characters that did know keeped her out of the looped until the point in the story were the mc oust him in fount of everyone. The only other time the fmc get a dark expression is when she is having sex with the mc and she is imaging him getting close to other women. I don't know how true this is but I have seen a comment that said that the mc forgot that their was a fanmade game that turned a character into a yandere. as for Ryo getting away Ryo himself said in a pass chapter that he had a goddess on his side if true then said goddess helped him escape. The only character that I know of that got mad about Ryo leaving the country was the married nurse thats why she want's revenge and thats why the married nurse is the new main villain.