Let's see. MillionaireMatch.com. Who cares about money? LOL!
When a woman tells me she doesn't care about my money, she has just told me that everything I have done to get it is of little interest to her and I am immediately deflated. This is not a positive comment, despite the intent of telling a man you are not a gold digger that is intrested in is money more than him. And, he knows you are lying. If you truly don't care about money, can I have yours? Please? Oh, so you do care about money.
Then don't say you don't care about money. Say what your really mean so that he does not misinterpret. You believe to convey, I think, that the fact that a man has a lot of money has it's draw but is not high on the list of characteristics that you find attractive. Excess money is simply icing, and that lots of money isn't a requirement or important enough for you to overlook the other characteristics that you find important.
When a man brags about money, he is trying to show you that he is a man of achievement, a winner, on top, a successful man and not a failure, and he is in no way saying he does not also have compassion, feelings, love, sensitivity, consideration, manners, honesty, or any other appealing characteristic. He just wants you to recognize his achievement and agree that achievement is a positive quality.
He wants to impress you. And in response you are unimpressed. He gets an F for wanting you and doing what he thinks will help make you want him. Give him a C for no affect, acknowledge that his impressiveness is implressive to the extent that it should be even if YOU don't care about it, and be nice. You ARE on this date to and it is not up to him to win you over. By defeating him, you have defeated yourself because a date that ends because his efforts were not the right approach to take with you is just as much your fault if not mostly your fault. He is trying, you are not.
Judging a man as a failure because he desperately seeks to cause you to find him great by telling you he is great is going to cause you to overlook men that otherwise have many positive qualities. Just because he sucks at winning you over and desperatley has put you up as the better person and hopes you will acknowldege his chest thumping and pull him up to your level or even place him above yourself does not mean that he isn't already the better person, it just means he lacks a skill that is mostly the domain of players anyway.
Give him a break and smile. He doesn't know any better and he just wants you to like him. Is is so bad that he wants that and isn't a good player? It does not define him and you should be happy that if this is a good one and you get him, you don't have to worry so much about other women, for he sucks at acting in a way he'd need to in order to get them.
So, when he braggs, your response would better be something like, "So, you are saying you want me and hope I will want back". Because that is the fact.