Doctor Love: Cheap? Penny Pinching? Smart?

Sunday, August 4th, 2013

Dear Doctor Love,
I have a group of friends who get together every week for socializing over dinner and a few drinks. One of the people is probably the cheapest woman who ever lived. If there is any way that she can get out of paying for her drink or her dinner she will do it. She uses such ridiculous things as going to the bathroom when the check is being brought to the table or “forgetting” to bring her purse. The peculiar thing about this is that, in our group, she has more money than any of us. As a matter of fact she is the only one of us that is wealthy, although you would never guess it from the way she acts.
I have known her for years and I accept her for the way she is. I personally never let her get away with sticking me for the tab, although she used to try it all of the time. The other people in our group have not known her for as long as I have. Their attitudes are very different from mine. This is starting to make the situation a little awkward.
Last week she had to leave the restaurant before our check was delivered. Once again, someone had to pay. Two of the guys in our group split her bill, which was for dinner and four drinks but that started a discussion. The discussion ended with most of the group agreeing that it would be the last time she gets away with being cheap. They appointed me to tell her the news because I’ve known her longer than anyone else and I’m the one who brought her into our social group.
Is there any way to do this without hurting her terribly? I don’t even want to do it at all but I can understand the point of the group.
/s/ Stuck With the Bill

Dr-LoveDear Stuck,
Don’t worry too much about hurting her. If she has done this repeatedly, she knows what she is doing. It is obvious that she plans to be missing when the bill arrives so. Even if she does it unconsciously, on a subconscious level she has to be at least slightly aware of her actions.
For some people, being tight with money is a kind of game. There is a group of people that, for lack of a better name, the Doctor calls the Unlikely Rich. These are people who are just like the rest of us, except that they are wealthy. How do they get that way when they have the same kind of jobs that the rest of us do? They do it by pinching pennies and investing the money wisely; even if it is only in a savings account. Even in this day and age, that technique still works.
Sometimes the game of saving ends up taking over the person’s personality. The Doctor knows a multimillionaire hotel owner who goes around town picking up beer bottles to sell for the deposit. He does not need the money but the habit to avoid waste is so ingrained that he cannot stop himself.
Explain this to your friend and warn her that she is in danger of letting her financial concerns ruin her social life. You will be doing her a favor.

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