4 Stories For Those Frustrated With Dating

frustrated with dating

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

Frustrated with dating? You need to read this week’s Love Essentially, in which I tell 4 of my personal dating stories. They will make you feel like your love life is a walk in the park! Or, they will just make you laugh. 

Dating is a tortuous but necessary evil. These 4 stories explain why.

by Jackie Pilossoph for Chicago Tribune Media Group

I have never met someone who actually enjoys dating.

What’s to enjoy? An awkward first meeting. A painfully long dinner with Mr. or Ms. Definitely Not Right. The disappointment of not hearing from someone with whom you were sure you hit it off?


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Dating is like a drug. No matter how many duds you meet, single people who are looking for that high off love, keep going back for more.

Why? Hope.

We’re willing to put up with all the jerks, liars, cheaters, womanizers and weirdos because, deep down, we know we only need that one awesome connection — that perfect person who will make all the less-than-perfect experiences worth it.

In other words, if you don’t play, you can’t win.




I didn’t get married until I was 35. Seven years after that, I got divorced and began dating again until I met my significant other at 49. So, you do the math. All in all, I’d say I played the dating game for at least 25 years of my life.

These days, my love life is picture perfect. But it took a long time to get here. The journey included a broken heart (multiple times), along with a roller-coaster ride of frustration, excitement, shock, disappointment and a weariness that made me want to give up and accept the fact that meeting the one just wasn’t in the cards for me. (Click here to read the rest of the article, published in the Chicago Tribune Pioneer Press, and several other newspapers across the country)

Like this article? Check out “Dating After Divorce: Advice, Tips, and Why This is an Exciting Time”


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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.

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