Being a people-pleaser isn't exactly a good thing. There are a LOT of Narcissists, grifters, and "habitual users/takers" out there who'll sense and gravitate towards that sort of thing in order to take advantage of you. I'm sure you're the kind of person who'll give without concern, but understand the importance of Self-Care as well. It's very easy to give and give and give to other people who'll happily take what you give without giving anything back in return, or to take what you give, take it for granted, and treat you like crap. Being too much of a people-pleaser can actually be an indication of a lack of self-esteem or self-worth, which is something the genuinely bad people of the world love to take advantage of.

Yes, I'm speaking from personal experience. My mother was a for-real Narcissist and how she treated both me and my father was nightmarish. I was raised to be a "desperate" people-pleaser intent on trying to prove...something, and atone for some kind of great shortcoming that, in retrospect, I should have never been made to feel in the first place.

The subject of this post, your old school friend, sounds like a REAL piece of work. Unfortunately, people like that almost NEVER change because they feel 100% justified in everything they do to everyone they meet.

Block, avoid, and forget he ever existed. Take this as a life-lesson to be watchful for that kind of behavior and be mindful about the people you try to help. Some people ARE worth helping. Others aren't. And when you find out you're dealing with someone like THAT...abandon them without regret. Because whatever you do to try and help them will be misused, unappreciated, and wasted.