Ask Mrs. Riches: Dutch on Dates

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Dear Mrs. Riches:
A few years post-divorce, I am ready to begin dating again. Despite the cringe factor, I have signed up with Match.com and have also let it be known to my friends that I am willing to be set up with their eligible bachelor friends. However, having met my ex-husband in college and gotten married shortly after graduation, I find myself very out of practice with dating. Can you give me the skinny on money matters and the modern date? For example, who pays if it's a setup in which the parties are strangers? If it seems like I make more money than my date, do I pay? If sparks are flying, is it safer to assume he will pick up the tab?  How do we bring all of this up in casual conversation? Please help me avoid making a fool of myself.
-- Dutch Girl

Dear Dutch Girl:
The simplest answer to your question is: Always be prepared to pay your own way. If you really want to err on the side of caution, carry enough money to pay his way, too, or at least to take an emergency taxi ride home. But you weren't necessarily asking for the simplest answer; you want the one that acknowledges all the complexities brought to light in the era of speed-dating, Internet match-making, and casual encounters at Starbucks, which all raise the question: "What constitutes a real date anymore?"

It's true that the word "date" used to carry a sense of gravitas, setting in motion an accepted protocol -- he picks up the girl, he pays, he delivers her home safely, and then waits gallantly to see if she will accept a kiss at the door. One look at reality TV shows like The Bachelorette and Big Brother will have you throwing those ideas out the window.

The modern date does call for a different set of rules and mores, both with regard to money and behavior. Unfortunately, "sparks" aren't quantifiable, and therefore the chemistry two may feel (or not feel) on a date isn't a reliable way to judge who pays. Making assumptions about income level or worse, comparing salaries, is clunky at best and may make aforementioned sparks a moot point. Without having contract negotiations before the date even gets off the ground, you're safest assuming that you'll take care of your own bills.

Think of it this way: If you enter into every dating situation prepared to pay your own way, you can only be pleasantly surprised when he insists on footing the bill. In the meantime, you have helped to preserve the "no expectations" clause that should accompany all dates with strangers -- whether they are registered with Match.com or simply happen to be friends with someone you know. If the date goes well and you're in for a follow-up, then you'll most likely begin to take turns picking up the tab. By then, you'll be on speaking terms -- or more -- and the two of you can work out the complexities on your own. 

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Fool contributor Elizabeth Brokamp is a licensed professional counselor who regularly talks money with her honey, Robert Brokamp, editor of The Motley Fool's Rule Your Retirement newsletter. The Fool has a disclosure policy.