My turn as the Love Doctor?

A female friend introduced her hot girl friend to a tall, mid thirties Wall Street guy with an Ivy MBA from Stamford. She thought he was perfect for her late 20's former party girl friend from CT who's now ready for a serious relationship. After a late night at PM Nightclub all three decide to share a ride home together in a cab.

When the new couple dropped off the woman who introduced them, Miss Matchmaker offered to pay for her share so she handed Mr. Wall St. $10. He accepted it and he gave her $5 back. Former Party girl decides to stay over Mr. Wall's place and in the morning says "Can you lend me $10 for a cab since I didn't have time to go to a cash machine last night." He cheerfully replies "no problem there's a cash machine in my lobby which you can use."

Now both Miss Matchmaker and Former Party Girl are completely turned off by Mr. Wall St.'s "lack of manners." They think he should be graciously paying all these "nickel and dime" expenses. They now consider him a cheapskate. And hot girls don't date cheapskates. So my question is: "If Former Party Girl is serious about getting into a relationship, should she reframe her view of Mr. Wall St. from "cheapskate" to "responsible guy who will never miss a mortgage payment?"