A Divorced Woman’s Really Bad Date

bad date

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

One of my friends recently began online dating after divorce. She met a guy on Bumble a couple weeks ago and they went out last weekend. Turns out, it was a pretty bad date. I tell her story and offer my advice in this week’s Love Essentially.

When Did Men Stop Being Gentlemen? 

by Jackie Pilossoph for Chicago Tribune Media Group

When it comes to men, I’m old school. I like a gentleman. I like a man who walks around and opens the car door for his date, a man who gives up his seat for a woman on the train, a man who asks a woman out on a date and pays for dinner, and a man who takes off his jacket and puts it on the woman he’s with if it’s cold outside.


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So when my girlfriend told me about a date she had last Saturday night, I found myself cringing. Why? Because her date was anything but a gentleman.

Here’s what happened. My friend connected with a man on the popular dating app, Bumble. The two set up a dinner date in the city, close to where the guy lives. My friend lives in the suburbs, but said she enjoys driving to the city for a night out.

It was the night of the big snowstorm, so her drive was long and a little bit stressful. When she got to the restaurant, she found a metered spot close by, but was having trouble with her credit card payment. She decided to leave the car, go into the restaurant, and ask her date to come out and try the machine.


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“You mean you want me to pay for your parking?” he asked.

This is the point when I probably would have said “Bu-bye,” but she didn’t.

“No, I’m just asking if you will take my credit card and see if you can get it to work,” she replied.

The guy obliged and headed outside. Second red flag: the guy (who had a short Uber ride to the restaurant) should not have accepted her card. He should have just paid with his own card.



A few minutes later…(Click here to read the rest of the article, published in the Chicago Tribune Pioneer Press.)

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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.

    5 Responses to “A Divorced Woman’s Really Bad Date”

    1. Wheeler

      I saw your article “when didnmen stop being gentleman? Just to say. We are still out there. Im am old school man at 52. My wife never has to open a door, put her coat on ( I even pull her hair out from under the coat, walk on the outside of sidewalk etc. Everyday I’m excited to hear about her day. We are still out there. I have taught my 3 sons those same skills. Good luck to your friend

    2. Joe Porter

      “Second red flag: the guy (who had a short Uber ride to the restaurant) should not have accepted her card. He should have just paid with his own card.”

      That quote is why men stopped being gentlemen. If females want everything to be equal (which is fair & I agree) then women can pay for their own parking and hey why not open the door for us equally? For every time I open a door it should be reciprocated the next time.
      Is it really fair that men have to do all the courting? Pay for all the meals, open all the doors, get the chocolate and flowers for V-Day. Not to me.

      • Jackie Pilossoph

        Who said anything about being “fair?” It was never fair in the history of men and women, but it’s nice. It’s classy. I’m not saying women shouldn’t open doors for men or treat them with kindness and love, what I’m saying is, when a man acts like a gentleman, it makes a woman love him more. And by the way, I do think some women, in their quest for equality, have lost sight of the fact that they are women, and that their will never be 100% equality, which is totally fine. That’s just me.

    3. Joe

      The great Dave Chapelle said, “Chivalry is dead. Women killed it.” Stop blaming and bashing men. Sex is cheap these days.


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