I felt bad for valintine when her old team died. I’d say spoilers, but it’s right in her charecter introduction so if you didn’t know before, oh well.
Playing valentines story mode, if my memory is correct, double basically trolls the last hope with copies of themselves before she kills them. Or at least I think she did that with hallow, who has a great design by the way. Shame they all died.
I'm sure Adam wouldn't survive for long after that pre-match line from Umbrella... I'm already in mourning.
Back to topic, I guess, Contiello's family and friends dying was extremely sad and horrible. And Filia's parents too, considering that they were murdered by their own relatives. Seems that the whole point of the story is that the Skullgirl feels like a lesser threat, compared to some people.
I'm gonna say Squigly's family and herself dying (and the audience seeing it) was downright depressing. And, just recently played Filia's Origin Story so, whew, was not expecting Marcus and Amelia to get got by Vitale... Talk about being done in by your own kind.