Dating Advice on Avoiding Losers and Attracting the One

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

dating advice

In this week’s “Love Essentially,” (published yesterday in Sun-Times Media local papers–first print edition, by the way!!) I give dating advice on things you can do to avoid losers and attract “the one.”


What do you think we should do for ourselves to draw a healthy, stable, loving relationship into our life?

Is it me, or is this a nicer way of asking, “How can I avoid picking complete losers and meet someone who is normal and who treats me well?”

In answer to this question, I first I want to ask: Why is it that when we go into one of those self-serve frozen yogurt places, like Menchie’s or Cocomero or Pinkberry that we sample different flavors before choosing the ones we want in our cup? We then peruse the fruits and the sauces and the candies before we “commit” to topping off our treat. Why? Because we want the perfect desert. So, why can’t we act the same when it comes to choosing Mr. or Ms. Right? In other words, why do people lower their standards and accept men and women who aren’t the yogurt flavors and toppings they really want?

Here’s why:

1. They have low self-confidence and think they are lucky that someone actually likes them.

2. They lack self-love and feel that this is the way they deserve to be treated.

3. They are afraid to be alone.

I will never forget the time I was at a restaurant and began talking to a woman who said her boyfriend was outside getting the car. As women tend to do, she and I began chatting non-stop, only to be interrupted by a very rude guy standing in the doorway with an angry face, shouting, “Let’s go, woman! Do you want a ride or not?”

Those were his exact words.

The woman, who instantly transformed from relaxed and happy to tense and worried, started to say good-bye when I asked her if she’d like to stay here with me, along with the girlfriend I was meeting. I told her we would drive her home.

She declined, at which point I said, “No offense, but why are you with that guy?”

The woman replied, “Because I’m in the my 50s and I don’t want to be single.”

As she walked off, the guy shot me a dirty look and then began yelling at her. I sat there with a look on my face probably resembling a little kid whose parents just told him there’s no Santa Claus.

Here are four tips that could take you from dating losers to a healthy, stable, loving relationship:

  • Give every guy/girl a chance. Not just the good-looking ones. Everyone brings gifts to the table. Being wise and open-minded will give you the ability to uncover the best ones.
  • Don’t ignore the red flags like you normally do. If he has six beers in the first half hour, let yourself see that’s excessive. If she spends the whole night talking about old boyfriends in a negative way, realize you could be next on her list!
  • Listen to your friends. They care about you and have your best interest at heart. If they’re not smitten, there could be a good reason why.
  • Like and love yourself. Make good choices that foster self-love, self-acceptance and inner peace. When you are happy in your core, you attract healthier relationships.


I conducted a poll on Facebook asking men and women, “What’s your number one criteria for your next boyfriend (or girlfriend)?”


Here are some of the answers I received: “Faithful, kind, attentive, honest, a true friend, appreciative, loyal.”


These are some pretty lofty expectations, but at the same time, shouldn’t the traits listed above be standard? I don’t know about you, but I’d rather be alone than settle for anything less than these.


It takes patience and strength to wait for the right guy or girl, and guts to move on if the person you’re dating is cheesecake frozen yogurt, when what you really want and need is cookies and cream!

Buy novels by Jackie Pilossoph



Featured Expert Articles

Jackie Pilossoph Jackie Pilossoph
Creator, Editor-in-chief, Divorced Girl Smiling
20 Things I Wish I Could Have Told My Newly Separated Self

20 Things I Wish I Could Have Told My Newly Separated Self

Elaine Koby Mossr Elaine Koby Moss
Vice-president and Senior Advisor, Vestor Capital
Want Financial Security After Divorce? Here’s Your Checklist

Want Financial Security After Divorce? Here’s Your Checklist

Dan Stefani Dan Stefani
Divorce Attorney, Principal, Katz & Stefani
Thinking About Divorce? Here Is Your Legal Consultation

Thinking About Divorce? Here Is Your Legal Consultation

Jeremy Woods Jeremy Woods
Senior Residential Mortgage Banker, CIBC
Your Mortgage And Divorce: 4 Reasons To Refinance ASAP

Your Mortgage And Divorce: 4 Reasons To Refinance ASAP

Leslie Glazier Leslie Glazier
Real Estate Agent, @properties, Certified Real Estate Divorce Specialist
Do I Have To Sell My House In a Divorce? Here’s What You Need To Know

Do I Have To Sell My House In a Divorce? Here’s What You Need To Know

Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

Leave a Reply

Your email address will not be published. Required fields are marked *