Dating in the 21st Century Cases #6 & #7

Photo by Huy Phan on Unsplash

In our ongoing effort to explore the current dating culture, we’ve heard about a variety of first-dates that went no further, due to fetishes, concealed marital status, unexpected nudity and public crying (his, not hers).

Today we discover that second dates can have their downside as well.


Brenda couldn’t believe her luck.  She met Dwayne online.  He was tall, good looking, well-spoken and took her to a trendy new restaurant.  (She’s a bit of a food snob, so this was big plus.)  They talked.  They laughed.

OK, in retrospect, he seemed a “bit off,” she admits.

The second date?  He invited her to a party at his home.  While eager to continue the relationship further, she arrived fashionably late, with the party in full swing.  As she moved from room to room, she noted most of the guests seemed a “bit off” as well.

Then she saw it.  They were all smoking crystal meth out of glass pipes (which she recognized from watching “Orange is the New Black.”) Brenda did not wait around for the police to arrive or Dwayne’s teeth to turn black.  She was gone.

Case #6

Michelle, who’s a sucker for romance, was swept off her feet when she met handsome, romantic Prince Charming, who sent flowers after their first date.

For their second date, he wanted Michelle to meet him in his neighborhood, at least 45 minutes from her own. She demurred.

“No problem,” says the charming prince, “I’ll send an Uber for you.”  He wouldn’t tell her where they were going, however.  It would be a “mystery date.”

Thrilled, she dressed up, had her hair and makeup done and chatted for 45 minutes to the driver about how excited she was.

“Do you want me to tell you where you’re going,” the driver asked.  “Oh, no, said Michelle, I want to be a surprised.”

“Surprised,” does not cover Michelle’s reaction when the car pulled up to a hospital where her date was waiting with his entire family.

It seems that Prince’s grandmother was being admitted, and he thought this would be a great opportunity for his parents, siblings and other relatives to meet Michelle.  Oh, but before they go to dinner, would she mind if they stopped at Granny’s to pick up a few things she’ll need in the hospital.

Michelle opted out of a third date, which didn’t kill the romance for Prince.  He sent flowers every Valentine’s Day until she finally blocked him.

What’s your worst date? Please use “comment” button to tell me about it.

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By |2018-05-08T22:58:42+00:00May 8th, 2018|Uncategorized|2 Comments

About the Author:

A former marketing executive, Judi Schindler, is a past president and founding member of the Chicago Area Chapter of the National Association of Women Business Owners. She is a member of the Leadership Team of Engaging Speakers and the Advisory Board of the Chicago College of Performing Arts at Roosevelt University. She’s listed in “Who’s Who in America,” “Who’s Who in American Women” and “Who’s Who in the Midwest.” Follow on Facebook, Twitter, Linkedin, Subscribe to “The Toilet Seat Must Go Down!”


  1. Gillian May 9, 2018 at 8:39 pm - Reply

    Worst Date: Well I’m not sure but actually I think this classifies as the most stupid date.
    The first couple of dates were fun. He owned a sailing boat. We went sailing along the coast from Boston. Lovely weather, I love sailing and I enjoyed jumping off the side of the boat and swimming to shore (he wasn’t up for that – he rowed the dingy). Then came the day he invited me to his home. It was a long time ago and I certainly wouldn’t do that today. I arrived and he invited me in. There in the middle of his living room was a rubber dingy and he invited me to join him in it (fully clothed thank you) and drink Dr Pepper. I’m not sure which was yukkier – the Dr Pepper or him! I suddenly remembered that I had to get back to take care of the two small children I was in charge of because the parents were going out. They weren’t of course, but I wasn’t hanging around to find out “what happens next?”

    • Judi Schindler June 13, 2018 at 12:34 am - Reply

      I am trying to picture the rubber dingy — you do mean a boat?

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