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When Gloria MacDonald matches potential partners, she says attitudes towards money are always considered. Ms. MacDonald, founder of Perfect Partners, says both men and women equally want a partner who shares the same financial values.

"Some have the mentality that you can't take it with you, others say you've got to save for a rainy day," she says.

Even if you have financial security, are you a Warren Buffett or a Donald Trump in how you choose to showcase your wealth? Ms. MacDonald uses a sliding scale to assess the financial compatibility of savers and spenders, and says if you're on opposing ends of the spectrum then the chances of the relationship ever working out in the long run are pretty slim.

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The beauty of a professional matchmaker is that you know some important financial facts up front. If you don't have a matchmaker finding financially compatible mates, when should you start digging on your own?

Asking about finances on the first, second, or third date is tacky, according to Ms. MacDonald. By your fifth date though, you're okay.

Between date five and 10 you should be talking money, according to dating expert and coach Christine Hart. "When you're sniffing around for status, do it naturally," she laughs. If it doesn't naturally unfold then offer up some of your own financial anecdotes to start the conversation. Mentioning you just opened a tax-free savings account, or just started saving for a place, is a start. Sharing your financial stories will help your date open up about theirs, she says. If an answer doesn't sit well with you, always follow-up. The reason for a zero bank balance and a rented apartment could be because of student debts and investments in other areas.

Having a money conversation in a new relationship can be awkward, but experts agree it has to be done. The earlier the better. U.S. financial guru Suze Orman even has a saying for it: "before you get involved in a relationship or anything, FICO first, then sex."

I tell Bruno Malta, a fee-based investment adviser with Wellington West Capital Inc., about Ms. Orman's words of wisdom. "Well, I've never brought my credit score on a first date," he jokes. "It's a mood killer." He agrees though that we all need to know where our potential long-term partners stand financially, but the real discussions don't need to come up until we're considering co-habitation. If you're apprehensive about the talk, he says start with the facts and create a net worth statement.

Couples who are committing need to establish a net worth statement and update it once a year at least, says Mr. Malta. It's an easy way to see where you are today and where you are a year from now. Is our debt going down and our savings going up? These are the questions you want to know. Mr. Malta says that two of the biggest issues for couples is debt load and how to combine finances. You should be on the same page with both issues.

Money and sex are two of the early-stage conflicts Ms. Hart sees with clients and she's never seen the issues just disappear. "Our relationship to money is far more important than what is in our bank account but if conflict pops up, it's here to stay," says Ms. Hart.

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If you've got different money personalities in the first five dates, you'll still have them in the next five months. The struggle to get on the same page then feeds into sex, socializing, and day-to-day living, according to Ms. Hart.

If you are in the early stages of dating it is important to have honest conversations about your finances. If you can get on the same page, and other high-priority values mesh, then you have a shot at financial peace. If not, you might want to chalk it up to irreconcilable financial difficulties and find a more suitable money match.

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About the Author
Angela Self

Angela Self is one of the founders of the Smart Cookies, a group of five women who specialize in personal finance. They are hosts of a self-titled show on the W Network and the authors of The Smart Cookies' Guide to Making More Dough. More

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