Doesn’t Everyone Have Dating Nightmares? Listen to This Guy’s!

I have to believe that everyone who has spent a significant amount of time dating has dating nightmares. I don’t mean bad dreams about dating, I mean they’ve met people who can be called dating nightmares!

I have a lot of personal experience with dating nightmares. Examples include a guy who started yelling at me (this was a first date, mind you) because a random guy started talking to me at the bar we were at. The guy told me he was upset because I looked like I enjoyed talking to the other guy.  Another dating nightmare was when I was dating a guy in my office, who was cheating on me with another girl in the office. We both found out a week later he had a third girlfriend who lived in another state! My favorite dating nightmare hands down is the time I was out with a guy and he got a text on his iPhone I happened to see that read, “Honey, we’re out of milk. Want me to pick some up before you get home?”  

But, as bad as I had it, author, Chad Stone had it just as bad if not worse! Here is Stone’s guest post, The Worst Dates EVER, where Stone talks about his dating nightmares. 

The Worst First Dates EVER

By Chad Stone


Back when I was a single man on his way to becoming a Middle-Aged Babe Magnet, I went on a lot of dates. Some were good dates, and some were the worst dates ever. Sometimes it seemed like I went on 1.7 million first dates before I met “The One”– the delightful woman to whom I am now happily married.

The worst of the worst dates were so bad I wondered if maybe I should take a vow of silence, become a monk, and never talk to another woman for the rest of my life.

One of my favorite bad dates actually started out really well. I met Elizabeth at a group dancing class. Elizabeth was an attractive woman in my age group in the class, and we got friendly right away. I asked her out, and I picked her up at her very impressive house. We went out to a local Country and Western club for a little bit of dancing, and then I took her to dinner.

Elizabeth seemed fascinated by every word I said, and I thought things were going great. Then she told me that she had 12 brothers and sisters, and her long distance phone bill used to be astronomical. She asked me what phone plan I had. She told me about how many friends she had overseas, and then asked me how many long distance calls I made every month.

We went back to her house for a glass of wine, and she told me that she wasn’t technically divorced. In fact, her “ex-husband” was still paying all of her bills—including her phone bills. There were so many red flags waving at me that it seemed like a Russian May Day parade from back when everyone in Moscow was a communist. Then she started telling me about the “opportunity” she was sharing with her friends about a new phone service. “Are you happy with your current phone plan, Chad?” she asked. To her, this wasn’t a date—this was a sales call. I couldn’t get out of her house fast enough.

Another one of my very worst dates lasted just six minutes. It was during a speed dating event, and Joyce should have been a great match for me because we had many similar interests. But she was sarcastic, bitter toward men, took herself way too seriously and was impossible to please. I could not get her to crack a smile. Listening to her complain was worse than fingernails on a chalk board. After three minutes, I started thinking about becoming a monk. The rest of the date was the longest three minutes of my life.

Another really bad date: My first dinner date with the Yoga Babe. She was the most beautiful woman who had ever agreed to go out with me. The Yoga Babe had long blonde hair, a perfect smile, and the body of a sex goddess. (I called her the Yoga Babe because I met her at a yoga class she was teaching.)

The Yoga Babe invited me to dinner at her house, and I thought we were going to have a sexy date for two. She had another agenda. Her 11-year-old daughter was part of the evening, and it quickly became clear that this wasn’t a date. It was a job interview. I was being considered for the opening for Step Father.

Now I love kids, but kids should not be subjected to their parents’ dating life until things are moving toward a long-term, stable relationship. The evening turned out to be a horrible experience for all of us. On top of that, the Yoga Babe couldn’t cook, didn’t know where her own silverware was, and only wanted to talk about Indian yoga gurus and her personal philosophy of transcendental parenting—whatever that was. By that time I didn’t care how beautiful the Yoga Babe was. I didn’t even stay for dessert.


Thanks Chad! I think the message here is that if you are going to go out into the dating scene, be prepared for dating nightmares. You could get lucky, but I highly doubt it and I bet Stone would agree with that. The good news is, there are so many wonderful men and women out there, and you have to date a few nightmares to find them. It’s kind of like shopping at Marshall’s. You have to sift through a ton of crap before you find a shirt or a sweater or a pair of jeans that fit and look perfect!



Chad Stone is the author of the critically acclaimed book, Confessions of a Middle-Aged Babe Magnet—One Man’s Brave Adventure into Dating Again in the 21st Century.” Chad lives with his wife in Santa Fe, New Mexico.

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Divorced Guy Grinning is a blog for men facing divorce and dating after divorce. It's kind of like hanging out with your platonic female divorced friend and hearing her perspective on your divorce and your love life issues.

One Response to “Doesn’t Everyone Have Dating Nightmares? Listen to This Guy’s!”

  1. Bella Fish

    Hi there,

    I’m a mature student at the University of Kent (England) doing a project based on online dating experiences. My project involves individual stories being told about dating experiences using either apps, or online-based websites. It can either be in the form of short stories, short videos, or recordings tell the stories.

    If you would be interested please let me know as I would love for you or some of your members to take part,

    Thank you,



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