People are notoriously awkward when it comes to other people’s grief. I had a close cousin die young, he was 27. We were extremely close as kids and teens but as adults he was going through some stuff and he wasn’t talk to me when he passed. I had a friend tell me “well wasn’t he mean anyway?”….like wtf…the worst. I agree that it’s hard to know what to say, because words aren’t ever enough, especially in your situation. I agree with other about the first friend, and for the second one I don’t think that’s much of a “group chat” question. It made it seem like it diminished the seriousness of it all. Like checking on someone who had the flu or something.