Help! I'm Dating a Cheapskate

In this economy, it pays to be frugal. But there's a difference between frugal and downright miserly. Here's how to deal with a date whose wallet never sees the light of day.

Help! I'm Dating a Cheapskate!
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He won’t pay for parking, so you walk half a mile to the restaurant. She claims she’s just old-fashioned, but she never picks up the check and your relationship is starting to feel like an “arrangement.” How did you get mixed up with this cheapskate, this person who is always out to save a few bucks, no matter how inconvenient or annoying the consequences?

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Can you learn to get along with such a tightwad, and is there any hope that your partner will turn into a generous human being who’s more into you than into his money? Here are some suggestions:

1. Recognize the Difference Between Frugal and Cheap

Maybe he doesn’t have the funds to splurge on an expensive restaurant or a high-end club. Since expensive doesn’t always mean better, anyway, try to create quality experiences on a budget. Pick up picnic basket fare from your favorite deli, throw in a decent bottle of wine, and spread out a blanket on a spot with a view. If the weather is no good for a picnic, order takeout and serve it on your best dishes, with candlelight and flowers to set the mood. Remember that being thrifty is actually a virtue, and don’t put pressure on your partner to spend money that he doesn’t have.

If your date has the money but just won’t spend it, she may just be stingy. Because she values money so much, she is likely to want to hold onto it, and this unwillingness to give may manifest itself in other areas of her life. Is she equally stingy with her time? Her emotions? You may have to make the call as to whether such a relationship is worth continuing, especially if money issues continually crop up.

2. Share your Values

Like most relationship problems, issues with money can often be settled with a frank conversation. Avoid an accusatory assault and instead focus on your own values and what you think is worthy of a splurge now and then. Is a night at the theater justified on your birthday? How about dinner out once a month, followed by after-dinner drinks at a posh club?

If money is in short supply, advocate saving up for a special meal out or volunteer to split the cost of a night at the movies (she can buy the tickets and you’ll pay for the popcorn and drinks). Look for coupons in the newspaper that offer discounts at restaurants or keep your eyes open for free outdoor concerts in the park. You can let her know that you are not a spendthrift, that you share her concern about wise spending and are willing to do your part to keep expenses within bounds.

You might also point out that there is such a thing as being penny-wise and pound-foolish: ruining a pair of expensive shoes by walking three blocks in the rain ultimately costs much more than valet parking, for example.

3. Decide Whether you can Handle the Cheapskate over the Long Term

You need to decide if your partner is by nature a generous person who just doesn’t have a lot of money at the present time, or if he’s just plain cheap. If he sees nothing wrong with being a tightwad, his habits are likely to cause friction in your relationship again and again. Add to this that his withholding ways may extend to other sensitive areas (time or even love), and you could have a big problem.

It’s well known that bad habits are not likely to improve after you get married, so if you’re hoping that things will get better once you settle down and share the purse strings, you are likely to be disappointed. You may be doomed to a life of chintzy gifts and cheap vacations spent in second-rate hotels. When it’s time to buy things for your house, you may feel forced into spending much less than is required for good-quality products. Is this something you can live with? If not, it may be time to jettison the cheapskate and look for someone who puts spending money in the proper perspective.

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42 comments on “Help! I'm Dating a Cheapskate


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Wow. There's a balance here. This one friend of mine married a guy SO CHEAP, when they went to Paris on their honeymoon, and he wanted to stay at youth hostels. She was all, "Beyotch, please. I am 35." This is a man who all of his clothes came from a dead uncle. Who would not order dinner when we went out in couple's groups to dinner. He would sit there and drink water. I could go on... I clip coupons, I scout deals, I go to matinees, and I save money, but I also love a great evening out at a fancy place now and then. You balance it out. I like to buy products made well that last, as well. I would rather blow my head off than marry a guy so cheap. Fuggedaboutitt.

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[I]It's an attitude issue more than a money issue. It's the complaining constantly about how much something costs that gets annoying. I have friends who are very frugal amazing savers, hardly ever spend money unnecessarily. And are at the same time super generous, the first to offer to cook something, or volonteer to help you with something, or just randomly bring you a gift like an easter card or a brownie, b/c they know it will make you smile. That spirit of generousity is very attractive in a friend AND in a potential date. Its not about the bucks its about the heart. And I think that's important whether you are male OR female. I am a woman, and I find generousity attractive in my friendships too. I adore my friends and they are all sweet, kind and generous, each in their own unique way. And that's obviously what I'll be attracted to in a partner, I don't expect perfection but I'm definately not looking for the antithesis of that either. [/I]

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