Beware of Bad Dating Behavior: My Story

bad dating behavior

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

I want to share something that happened to me while dating in an effort to make a few really good points about bad dating behavior and why you should steer clear from someone exhibiting it.

Several years ago, I met someone in a business setting, who subsequently called and asked me out. We set up a night and time to have dinner. So far, so good. A day before the date, he texts me and says something like, “hope we’re still on for tomorrow.” I text back, “Sure, looking forward to it.” We set a time and restaurant.


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The next day comes along. It gets to be around 2pm and I haven’t heard from him. The date was set for 7pm. I texted him and said, “Just making sure we’re still on. Want to meet there? Should I make a reservation?” At this point, I’m a little annoyed because it might have been nice for him to make a reservation and offer to pick me up. Is that too much to ask? Am I being high-maintenance? I don’t think so.

Here’s where the bad dating behavior begins. I get a text back that says he has to cancel because a close friend had a family emergency. I’m not heartless or so self-centered that I don’t understand, but here’s where I have a big issue.

Was he going to text me and tell me this? In other words, I texted first. Was he not going to text at all? Was I going to be stood up? Or, was he going to text me at 5pm? Or even 4pm? Or 7pm? My point is, I am a single mother working full time who like most people have limited free time. Did it ever occur to him that if he cancelled, I might want to make other plans? Maybe call a girlfriend for dinner or go to a movie? This is a kid free night for me. Any single parent can understand how you might want to take advantage of that, right?



What I learned from this bad dating behavior is that this person had no regard or respect for my time. But let’s even give him the benefit of the doubt and say that he coincidentally just found out about his friend’s emergency 10 minutes before he got my text, and hadn’t had time yet to contact me. Shouldn’t he have picked up the phone and called me so that I could hear the tone in his voice? So that he seemed sincere? If the situation was reversed, I’d have called him and said the following:


“I am so so sorry that I have to cancel. I feel terrible about it and I really do want to go out with you. Can we make a date right now? How is next Tuesday?”


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The reason I would do that is because I would want the person to know that I was sincere, and that he shouldn’t take it personally.

But let’s say the whole thing was a lie–that there was no emergency (although I don’t think that is the case. I will never know.) But let’s just say he changed his mind and didn’t want to go out with me. If it was me, I’d either go on the date and keep it friendly, or I would cancel and just be really honest. Maybe say, “Just feeling like I have too much baggage right now and don’t feel up to it.” However bad it is, the person would probably be livid, but would respect the other for being truthful.

To top things off, he then texts me a couple days later and says, “Just wondering what you are up to today. Want to get together?”

I politely declined, as I no longer had any interest in getting together with this person.

Here’s the thing. In many ways, dating at my age is much much different than it was before I was married, one being that I am going to recognize red flags very very early on. Does that mean I won’t give someone a second chance? Maybe, maybe not. It all depends on my gut feeling.

I just know I’m not settling for bad dating behavior this time around, like I occasionally did, looking back to my twenties, thirties and even in my early forties. It’s not good for self-esteem and for anyone who seeks a healthy relationship.It’s better to be alone than to feel like that.


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In closing, I just want to say that I don’t think this guy is a bad person. Actually, I bet he is nice person. But, for me, he’s the wrong person. Why? Because bad dating behavior can only lead to more bad dating behavior, and it just makes you feel bad about yourself for settling for it. In other words, the relationship is already tainted. Not a good way to start off with someone.

Dating that is stressful or disappointing, or that makes you feel rejected or disrespected isn’t good. Dating is supposed to be fun. It’s meant to make you happy. So, seek out good dating behavior instead. And great dating behavior—well, that just makes you feel like you can fly.

Like this article? Check out, “Dating Someone Who is Hot and Cold can Really Burn

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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

    3 Responses to “Beware of Bad Dating Behavior: My Story”

    1. Emad Missak

      I can understand her feeling that the red flags, bells and whistles are everywhere. But after my divorce I attended a seminar on life and realized that half of the conversations perceived are only in our heads we prejudge, criticize and subconsciously critique everyone based on these “feelings” if I were her I would’ve took the initiative and called him to hear his tone using an the excuse that was worried about the friend or put phone in pocket and it butt dialed. But we all need to realize we all have busy schedules and lives and just be understanding of this fact. And put the human contact and understanding back in dating.

      • Kimberly

        I agree with you, Emad.
        —Being involved in an emergency (even for someone else, not personally), there likely was so much adrenaline/upset/rushing around that calling her could easily have slipped his mind until later.

        I wouldn’t have lied to him about calling by accident, though. Would have said I wondered whether there was something I could do to help. That would have provided the side benefit of getting the opportunity to “read” his honesty, etc.

    2. Lamonica

      Oh my I totally have encountered some bad dating behaviors, as well. Just encountered one on yesterday. I plan to blog about that nightmare on my blog very soon. Yes, I’ve learned a lot about myself since my divorce and I realize that I deserve to be treated with respect…anything less is not acceptable. Enjoying your blog!


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