We have a friend similar to this guy... It does get old when you must battle over who pays for what, etc... It is an ego thing with our friend, and he takes it to the wall every time. He even goes so far as to get money from his girlfriend (who does not have it to spare) to throw around and play the "big-shot."

He loves to brag about spending money on other people, and makes up stories to tell us about it... I feel bad when he does this because we all know the stories are more fantasy than reality. He has seen a therapist who advised him that he has low self-esteem, and tried to help him work on it. He now declares that he was totally "cured." He is impossible to reason with.

However, this guy is really a decent man, and a true blue friend. So we tolerate his quirks, and try to gently steer him in a sensible direction when we can. He will allow us to pay for meals part of the time. We will never abandon him since we're about the only friends he has.