How to Stop Dating Losers and Meet Someone Meaningful

dating losers

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

A DGS reader asks: What do you think I can do to draw a healthy, stable, loving relationship into my life and stop dating losers?

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 are a few possible reasons people are susceptible to dating losers:

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.


Tiffany Hughes Law



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

1. Be open-minded and give every date 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.

2. 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!


Katz and Stefani Family Law Attorneys


3. 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.

4. Like and love yourself.

Tell yourself (and mean it) that you deserve to be in a healthy, meaningful relationship. 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 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 person, 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!

Like this article? Check out, 9 Signs of a Healthy Romantic Relationship


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    Editor-in-chief: Jackie Pilossoph

    Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. 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.

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