I imagine I'd try and flip the awkwardness, calling him out on being overly sensitive regarding his newly departed wife. It wouldn't be a conscious plan, it would just kinda happen.
I mean, It'd not be fair to spring a dead wife on me in a conversation, that requires like professional level social interaction skill, and I haven't even managed to figure out the basics yet.
So like, poor him and his hypothetical dead wife I guess. But how does he think I'd feel when he doesn't laugh at my "too soon" jokes?
What's always awkward is the Twogag facebook page.
You'll feel right at home.