I've just had a tough conversation with my friend whose grandfather has passed away very unexpectedly yesterday. They're also going through a breakup and a few other bad life events have happened to them recently. I've never been the best at condolences but this was much more difficult than usual because they're having an objectively bad time, many bad things happening at once. We're supposed to speak again tomorrow but I felt a bit taken aback by how much they're going through (I only just found out their relationship had ended too), I was really left lost for words so I did just say "I don't know what to say" which really isn't helpful, it it? Any advice on what to say (or what not to say!) would be helpful.