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Cheapskate… Or Money-Smart Date?


With the economy making misers of us all, how can you tell a cheapskate from someone who’s simply being frugal? Here, we offer tips to help you spot a smart money honey.

By Kimberly Dawn Neumann

s your date putting you out? We mean financially! No doubt courting Mr. or Ms. Right can become a pricey proposition. And in this penny-pinched economy, dating and money can definitely become issues. But while spending beyond one’s means is not attractive, neither is being frugal to the point of
Your job is simply to observe and put the pieces together.
not having fun. So how do you know if the person you’re dating is being economically conservative or flat-out cheap? Cash in on the following advice from top financial and dating experts to spot a smart money honey.

What Constitutes a Cheapskate?
The first thing to keep in mind is that being a cheapskate or a money-smart dater has less to do with the current economic climate and more to do with mindset, philosophy and approach to money. “Someone who earns a lot and has accumulated assets can be a cheapskate while someone who has modest means and little to no assets can be extremely generous with what they do have,” says Jacquette M. Timmons, financial coach, trainer, and author of Financial Intimacy. “Daters need to recognize that it takes time to determine a person’s financial style and it is the person’s behavior that will provide the necessary clues.” Your job is simply to observe and put the pieces together.

So how can you tell if someone is being cheap or just penny-pinching? Look at these five clues.

1. Gauge with your gut
The main difference between a cheapskate and a money-smart dater is usually how it feels. “If it feels bad it’s probably cheap,” says M. Gary Neuman, author of In Good Times and Bad: Strengthening Your Relationship When the Going Gets Tough and the Money Gets Tight. “The most important thing is how your date reacts to your wishes, especially when they don’t fit into the ‘plan.’” One rose beautifully presented feels good. Someone controlling your meal choice does not. A cheapskate is not likely to be flexible or present alternatives when you want to do something that isn’t in the pre-planned budget for the evening, which indicates less concern about pleasing you than preserving his or her own thrifty desires.

2. Beware of flashy over-spenders
While you might think that the big spender is the non-cheapskate, it actually could be quite the opposite. “Does your sweetie always insist on picking up the check at a big dinner and/or throw down his or her credit card without even looking at the bill? While this could be a sign of innate generosity, it could also be a red flag for someone who is trying to show off and is doing so by living beyond his or her means thanks to the ‘friendly’ help of credit cards,” says Manisha Thakor, author of Get Financially Naked: How to Talk Money with Your Honey. “The unfortunate reality is that over two-thirds of Americans routinely live beyond their means…in today’s credit-driven society, the guy with the big house or flashy car or the gal with the expensive handbag and designer stilettos may well be presenting an exterior image that bears no resemblance to his or her true economic reality.” In other words, watch out for impulsive or compulsive spending as those are not true hallmarks of wealth and could actually indicate financial immaturity or
Everybody is being cautious with money in this economy.
problems — which is far worse than someone simply being cheap.

3. Look for non-fiscal generosity
“It is very important to look for generosity in a person — and this has nothing to do with how much money someone makes or has in the bank,” says Dr. Bonnie Eaker Weil, prominent love expert and author of the bestselling book Make Up, Don’t Break Up: Finding and Keeping Love for Singles and Couples. “Everybody is being cautious with money in this economy, but a generous date will try to find ways to show you a good time while still maintaining budgetary balance.” In other words, if your date offers to cook you dinner at home so you can attend a Broadway show together, that is a sign of generosity with fiscal prudence. There are other ways to be generous as well; for example, spending time together (i.e., helping you with a project) or routinely looking for ways to make things easier for you. These all count in the dating equation, so pay attention. These actions may indicate selflessness and a true desire to enhance your well-being, which is something that money cannot buy.

4. Don’t be afraid to talk about traditional gender roles and money
“If money is not talked about early on, it can be a smokescreen to cover your date’s fear of someone getting close,” says Weil. Even before the economy tanked there was some confusion about traditional gender roles and money, as one-fourth of women are the breadwinners in their households and two-thirds of women are working outside the home. However, studies still show that men who are the family’s source of financial support have happier marriages. “What that means is it still affects men psychologically if they can’t provide adequately on a date,” says Weil, who suggests broaching this touchy subject in a validating manner in order to separate true cheapskates from singles who are simply fiscally cautious. Try casually mentioning the issue to potential dates early on. For example: “Since money’s such an issue these days, I wasn’t sure if you wanted to go Dutch or take turns when we go out. What do you think?” This will open a dialogue about money in a non-threatening way. It also allows the other person to counter with options: “I would prefer to go somewhere I can afford and could treat you, but if you prefer something more expensive and don’t mind splitting the cost, I’m open to suggestions.” This gives both of you economically viable date options while still protecting everyone’s ego.

5. See how your date manages expectations
One really good clue is how open someone is about his or her current employment status (maybe your date is currently unemployed, building a business, etc.). An honest discussion about someone’s employment status gives you a better idea of what you date can or cannot do. “Cheapskates are usually not generous in spirit and therefore have no interest in helping to manage your expectations,” says Timmons. “Sometimes people also do things to ascertain your motives; they want to know if you are interested in dating to find out who they are as individuals, or for what you believe they bring to the table financially.” Pay attention to creativity. Someone who doesn’t have a lot of financial liquidity but comes up with innovative dates — like taking you to every hot dog stand in the city to compare and contrast — is being an economy-smart dater. “A prudent person recognizes that it is about the experience and building a connection — and will look for creative ways for you two to get know each other better without breaking the bank in the process,” says Timmons.

In other words, a bulging wallet doesn’t necessarily make your date the most generous companion. On the flip side, someone who is truly giving will be concerned about you having a good time within the confines of his or her unique financial situation. And that is someone you definitely want to date!


Kimberly Dawn Neumann has been called the “Carrie Bradshaw of Broadway” due to her two careers as a performer and writer. The author of two books — The Real Reasons Men Commit and Sex Comes First — and countless magazine articles, she’s also the founder of DatingDivaDaily.com.
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