5 Tips For Saner Dating

To make the right decisions in love, you need to use your head as well as your heart. Here’s how to do just that—and win big in the long run.

By Veronica Chambers

hile many a rapper has proclaimed that there is “no romance without finance,” I never once thought to liken my love life to my investing strategies. But when the idea was suggested to me by a good friend who was an editor at a financial magazine, I got to thinking: People lose money in the stock market all the time by investing with their hearts, not their heads; likewise, people lose out in relationships by choosing to ignore even the most obvious signs that they should jump in, hang on, or cut bait. The longer I thought about it, the more similarities I found between building a nest egg and finding someone to spend the rest of your life with. What if I could apply some financial savvy to my dating life—would my search for Mr. Right finally pay off? In my experience, you can count on it. Here’s how to use a little logic to reap many happy dating dividends in the months and years to come:

Investment tip #1: Build a dating ladder
Taking the advice of my financially savvy friend, I decided to create a dating ladder—a version of an investment ladder many people use to build a strong stock portfolio. In
Instead of falling madly in love on the first date, I needed to diversify by building a “dating ladder.”
an investment ladder, you distribute your money over various stocks to reduce your risk. Similarly, instead of falling madly and hopelessly in love on the first date, I needed to diversify and see a few people until I was sure that one investment—or in my case, one guy—was actually going to commit to a relationship.

This meant that instead of worrying whether Mark, the starving artist I’d been seeing, was going to ask me out on a date Friday or Saturday night, I should make my own plans—say, spend Friday having dinner with a friend (and mini-crush) who’d just moved to the city and on Saturday go out on my own and perhaps summon up the courage to ask a new guy out. That way, by the time Sunday rolled around and Mark asked me to gallery-hop with him, it seemed like a perfectly lovely thing to do. He was just one rung of my dating ladder, after all.

Investment tip #2: Don’t always go for gold
Alas, life is not like The OC; few of us live in a world where we juggle two or three good-looking, charming prospects at one time. But if your dating ladder is to work, you have to fill your dance card with something besides the person you hope will become your one and only. One idea is to reserve a Friday or Saturday night for a platonic date. Go out with an old college friend to a great restaurant or invite an interesting work colleague to a play. For months, I had a standing Saturday night date for a private tennis lesson. Sure, I knew that I was just swatting balls and getting a workout, but the message this sent to guys I was dating was that I was busy, period. Author and life coach Sophfronia Scott sees platonic dates as a great way to keep your sanity when you’re dating. “One of the suggestions I give clients is to behave their way into the life and relationships they want to have,” says Scott. “Platonic dating is a perfect illustration of this. Dating platonically is a great way to remind yourself of the way you want to feel on a date: Relaxed, comfortable, just being you! The more you practice, the more you know how that feels.”

Investment tip #3: Don’t throw bad money after good low and sell high.
But sometimes (a lot of times, actually), that hot stock you gambled on keeps tanking—and you have no choice but to buy high and sell low. Dating is no different: In the classic film, Every Girl Should Be Married, Betsy Drake chases after Cary Grant. At one point, she admits that she is sick of the way he’s ignoring her, but justifies her efforts by saying, “I spent two week’s salary on this dress, on this dinner, trying to impress you.”

We all do similar things in real life: We hang onto relationships because the person seems like such a hot investment, or we’ve put in so much time and effort into one person that it seems like we’ve got to hang on for the payoff. But relationships gone sour aren’t that different from investments that have gone south. So, don’t throw good money after bad. Know when to move on, especially in those first few months when you’re getting to know someone.

Investment tip #4: Date like a millionaire
One question that financial advisors (and therapists, for that matter) like to ask clients is, if money were no object, what would you do? Your answer is an amazing
Many of us are waiting for the perfect relationship to do the thing we most desire. So what if you’re single; what’s really stopping you?
bellwether to your heart’s desires—and what quickly becomes apparent is how attainable those goals truly are, regardless of your financial situation. For example, you may need to be a millionaire to buy a sailboat and sail around the world, but you don’t need limitless cash to take a sailing lesson or set up a “sailboat fund” where you throw in ten bucks a week.

Similarly, many of us are waiting for the perfect relationship to do the thing we most desire: Buy a house, get a dog, join the Sierra Club. So what if you’re single, what’s really stopping you? There’s no reason to put off pursuing your dreams, and doing so will only frustrate you further. Life coach Scott always advise clients who wish to be in a relationship to spend as much time nurturing those wants as they do looking for a partner. “The idea is to get them excited about living their life and having fun,” says Scott. “They may not realize it, but when they start living and having fun is when they start looking more attractive to potential mates!”

Investment tip #5: The market always corrects itself
From the Depression to Black Monday, people have lost millions in the stock market. But ask any financial expert and they will tell you, it never pays to keep your money underneath your mattress. Over the years, you always make money in the stock market because the market always corrects itself. Similarly, it doesn’t pay to give up on dating. A friend of mine, who was sick and tired of being sick and tired, announced at a party that she was begging someone, anyone to set her up. Three months later, she is dating the most amazing guy she’s ever met.

I, too, know what it’s like to want to give up on the whole enterprise. Not too long ago, I had endured the worst, most humiliating breakup of my life. By my own estimation, I gave myself six months to start showering on a regular basis and another six months to stop breaking out in tears for no apparent reason in the middle of the day. I’d planned for a solid year of mourning because well, dammit, I deserved it. Then two weeks later, this guy called me up and asked me out for dinner. I didn’t want to go—in fact, I was convinced that there was milk in my refrigerator with a longer expiration date than this man. But I took a shower. I packed a purse full of tissues. I went out to dinner, and I had a lovely time.

Even though he claimed to be smitten right away, I stuck with the dating ladder and continued going out on platonic dates with other people. When my ex-boyfriend came back around, I made the difficult decision not to throw more good money after bad. In less than a year, the man who’d asked me to dinner when my heart was broken had proposed. Confident that this was the best investment I could possibly make, I said yes.

Veronica Chambers is a novelist living in Los Angeles. You can reach her at
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