Dating The Guy From Hell

dating the guy from hell

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

“What the hell?” a divorced woman asked on a Facebook group page. Here is her story in a nutshell and my advice on why she shouldn’t be asking “What the hell?” but rather why she should be asking herself “Why am I dating the guy from hell?!”


This woman (who is divorced with kids) connected with a guy she grew up with on a dating app. After a few text exchanges, he told her he didn’t want to date a woman with kids. She reached out to him after hearing some sad news about a mutual friend. They decided to meet at a bar he goes to often. They hit it off immediately, kissed in the bar, went home together and had sex.

 Two days later, she didn’t hear from him so she texted him. He responded with a brief answer, and then she responded with another question and he didn’t answer for 3 days.

 She texted him again a few days later and his response was a smiley face. She then called him. He has not called her back.


Here’s what I have to say about this.


I have such a hard time with this story because why is this woman surprised at how all of this has unfolded? She basically chased him like a cat and mouse. Why would she subject herself to that?  What happened to her standards? Her self-respect? Her self-esteem? When did the bar get so low? Does she think because she is divorced and a single mom that she can lower her standards to the point of having this guy treat her like crap?


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Listen to me. This guy is a piece of garbage. Let’s begin with the fact that he said he didn’t want to date someone with kids. I actually respect his honesty. He has the right to feel that way and I would not judge him for that.  But, why the hell would he agree to go out with her unless he was only in it for a fling? He wouldn’t. What a user!


But, I do have to say that this woman sort of did this to herself. She knew what she was getting into when she asked him to get together and she knew he didn’t want to date someone with kids.  Did she think he was going to have such a wonderful time on the date, that all of a sudden he would change what he wanted in a woman and want to be a stepfather?  In effect, he had already broken up with her before they even saw each other! So, why would she want to take that risk? Why would she want to set herself up to just feel shitty?


To make things worse, she slept with him! I’m not judging someone for having sex on a first date (even though I’m not a huge fan of it.) But, I’m judging that her subconscious knew he wasn’t interested in her. She knew it before they even met! So, unless she wanted a no-strings-attached affair, (which she didn’t, otherwise she wouldn’t have called him a few days later) why would she have sex with him? Doesn’t she think she deserves to have sex with a man who wants a relationship? A man who will text her 5 minutes after she leaves his house?? Doesn’t she feel she deserves a man to be completely into her and love and cherish and adore her? –especially after the devastation of a divorce!


Another red flag by this jerk: sleep with the girl and then nothing. No text, call, contact. So mean. One option would have been to call her and say he just wanted to be friends, that it was nothing personal, but that he didn’t want to date someone with kids. That would have been the classy thing to do. Instead, he goes dark. AND, they knew each other growing up! That’s even worse! How can you do that to someone you grew up with, let alone anybody? I just don’t get it.


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Lastly, why on earth would this woman text and call him?? Why is she chasing him? All that does is make someone feel even worse about themselves. Trust me. I’m not judging her because when I was younger, I let some men treat me badly, and ran back for more. So I get it. I just wish something would click and she would realize how badly she’s being treated and just be done with him.


When people are dating after divorce, we owe it to ourselves to not settle, to recognize red flags, and to make sure we get rid of anyone treating us even remotely badly . I know it’s hard. No one wants to be lonely or be alone. And I know it’s hard to meet people, so people dating tend to brush red flags under the rug, because they think “Maybe this is the best I can do.” I do understand that and I am empathetic.


But, my advice to anyone who wants to be in a truly happy and fulfilling, authentic relationship is to make sure that you feel like you are in heaven, and that means staying away from the guy from hell!

Like this article? Check out, “Mixed Signals Means She’s Mixed Up




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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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