Alright, so, I'm dumb when it comes to dealing with people beyond the most completely superficial interaction.
I have a friend of mine from high school/college that I haven't seen or kept in touch with for like the past 4 years. When I say friend I mean like... casual video game/D&D pal who I always hung out with in a group. So not very close. Randomly got a message from him via a site we had worked on like 5 years ago sending him updates when I was randomly tweaking it. Since I'm in back in town for Christmas break I figure, why not catch up.
Now, his younger brother was killed in September this year in a freak accident. I heard about it from my mom shortly after it happened, but I'm not on facebook, don't have a phone number/e-mail for him, so I couldn't offer my condolences then. The appropriate thing to do would be to offer my condolences when we meet up again, right? I just don't know if I should bring it up right away, or like... wait for him to mention something or what. And since we're not close it seems weird to go from like "Man, I'm really sorry about your brother" to "How bout dem video games?"
I don't know. I'm dumb at people and haven't really had to deal with this. I'm probably overthinking it but it's a sensitive subject and I don't want to fuck it up. Especially since it's the holidays and it's probably gonna be fuckin' rough...
So. What do?