Loosing a close loved one is really disheartening. I empathize with your friend and I hope that he will get through this phase soon.
For your question on how to comfort a deeply grieving person, hmm, sincerely for me, I refrain from saying "sorry" or "I understand" rather I stay mute allowing the grieving person to pour out all the emotion they can as that would help them heal better and come to terms with the current situations of things. After the emotional ride, I do the work of an encourager by letting the grieving person understand that this is a phase of life but it will get better with time.
Thanks for your concern Becky, your tips are really helpful my darling thank you again and again and compliment of the season🤗
You're very welcome dear 🥰