She swallows a bit, drumming her fingers against her glass for a moment as she tries to figure out how to do this. Awkward, so probably after they broke up. That, at least, is a good start. "It's really great, you know. About your mom?" That seems like a safe enough question to ask, given that it will tell her about when he is.

Either before or after his mom died. Meaning there were quite a few different levels of awkward.