American English – Meaning of ‘Hi, How Are You Doing?’

“How do you do” in modern American English is a formal noise made upon meeting someone. It rarely, if ever, indicates actual Interest in an answer. It can be acknowledged by repeating the same phrase back, or by saying “Very well, and you?”, to which the answer is also “Very well”. It can be abused as an opportunity to seize control of the conversation by interpreting it as one of the others, but that's rude.

“How are you” is an inquiry about the person's health, usually physical but mental/mood is included . Again it's often just a ritual, a friendly greeting, but it's not unreasonable to give a real answer to this one: “Great except for my allergies kicking up”, for example. Generally the answer should be brief, so the querant can decide whether they want to ask for more details or not. But in most cases, some version of “Fine, and you?” is the right ritual answer unless this is asked by a close friend or your doctor.

“How are you doing” is a more general inquiry about how your life is going. Depending on context and intonation, it can range from another ritual greeting (fine, and you?) to a deep expression of concern (which can be brushed off with the ritual answer or given a more meaningful response).

Exceptions abound, but those are the most common usage patterns in my dialect, anyway. (NE US)

There is nothing wrong with saying You are a good man.

After he's told you he's been to the cemetery, you could open up the conversation by saying I see you've gone there often. You must really miss whomever. What were they like? Sometimes it is good to get the bereaved to recount the good memories.

What's most important is he will feel what your intention is when you talk with him. Be of good heart and good intentions.

I realize this is a sensitive subject, it's just a suggestion, please no flaming...