-He talks about his childhood/young adulthood endlessly
-how his father bullied him
-how crap school was
-I feel it's totally inappropriate for me to say how secure I felt as a child and what school did for me etc.
-He doesn't seem that interested in my past experiences so I never really talk about them and if I did, he wouldn't be able to relate to them anyway.
-I realise what a hold his past has over him, as if he's constantly trying to come to terms with it.
-And that includes his failed marriage -divorced twelve years ago but still bears his ex a grudge
-the fact that he could have been more successful, like most of his mates.
-I feel sad for him in a way and just wish he could put it all behind him.
With the greatest respect, I don't think this has anything to do with your education, as his 'lack' of education.
Breaking down your last post into bullet points as above....
Bears his ex a grudge years later. Bears his school a grudge, his father, everyone is to blame but him.
Many many people had a poor upbringing, poor schools, and so on. The point about becoming an adult is that you do something about this, not resent others who you perceive to have had 'advantages'.
The pity hook is also a huge red flag.
Sorry if I am miles off the mark.
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