It's sounds like he is a bottomless well of need. I have had some friends over the years who become very dependent on anyone who try's to help or reassure them. It can become exhausting, they can suck the life out of you and seem to be oblivious of the toll it takes on their friend or friends.
I remember a relative calling once, asked me how I was doing, I said I had the worst possible days in a long time and needed to rest. They answered, yeah, I had a bad day too, then proceeded to stay on the line for 15 minutes complaining about co-workers, traffic, car trouble until I was about to slit my wrists. They never did ask me what was bad about my day. I don't know why that happens.
On the other hand, I have a good friend who I have known for decades. When our 13 year old Vizsla was gravely ill, she would call about Sadie, but she waited until we had to put her down before she told me her Aunt had terminal pancreatic cancer. I would have wanted to know, I love her family, but she was afraid it was piling on too much while we were caring for Sadie. I understood why she waited, we've all been thru some serious life threatening illnesss,, thankfully not at the same time. But that a little different than being worried that you aren't smart enough and insisting someone at their mother's funeral spend all their time propping you up.
Before anyone mentions it, I know we aren't talking about funerals, it was used as an example.