Doug's method of teaching Brian about Coral was totally unacceptable
In what bizarre universe did Doug think that would work out ok with Brian? It was completely unethical.. no wonder Brian was angry.
shareWell a few things.
Doug was completely out for himself. As he even said, "Had to get my money back."
That said, I think Doug also realized Coral was just money and not really worth anything. She was just a whore and looking to score with the good looking guy, not wife material and certainly not anyone to maintain a long term relationship with. Any girl that would not even talk to Brian and just make out with his friend and have sex with him (whether or not he told a story to her) is complete trash IMO.
The way Doug played it off, it was almost like, "Dude, had to get my money to win that bet. You're REALLY going to be pissed off about that?" Brian was young and naive and I don't think Doug wanted him to turn out like himself... 40 and chasing rich chicks who aren't sincere and just treat them like little play things.
*spoilers* Brian eventually figures that out when he hooks up with the rich chick that he dumps at the art gallery and then it fully hits home after he finds out that Greg took his life, hence why he goes back to Shue's character.
Brian's perception on money was just as F'd up as Doug's and ultimately it ruined Doug's life. Shue's character sees this as well, "Because you're so wrapped up in money, I wanted to know how you felt about me.... ME!!!" Doug taught Brian a lot in the end and Coral was nothing more than money and a squeeze.
While I don't agree with it, I think Brian ultimately realized it and that's why he was so welcoming when he saw Doug in Jamaica. Even Doug said, "You'll thank me some day..." and Brian definitely did by the end of the movie.