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Dating After Divorce: How To Answer “Why Did You Get Divorced?”

Written by Jackie Pilossoph. Posted in dating, dating after divorce, Dating over 50


dating after divorce






When it comes to dating after divorce, the question “Why did you get divorced?” undoubtedly comes up. Right? I mean, can you blame someone for wanting to know?


As a person who has experienced those conversations, (both the one who has asked the question and who has been asked) I can honestly say that when people ask “Why did you get divorced?” or “What happened in your marriage?” they know they aren’t getting the full story. They are hearing their date’s side of the story. What I wouldn’t give to hear the responses of some of the ex-wives of the guys I’ve gone out with, but that will never happen. I’m sure I’d get a totally different perspective, which might or might not have an affect on the way I view the guys.


So, if we ask our divorced dates why they got divorced, and we’re only getting one side of the story, why do we want to know? Because we want to hear what they have to say. We want to see if there’s bitterness in the answer. We want to see if things add up. We want to gauge the sincerity of the response. Because even from one side of the story, we get the landscape of the person’s situation.


A few months ago, I met a guy on Facebook who was newly separated. We decided to meet at a bar. I felt more comfortable with my friends around, so I made the evening a group get together.


The four of us talked a lot and eventually it was just he and I in a conversation. And, I say, “So, why are you getting divorced?”


His response was, “Well, my wife and I were going through a tough time and I did some things I probably shouldn’t have.”


I sat there listening with what I thought as an empathetic look on my face, but inside I said to myself, “Boom. Deal breaker. This guy is a cheater. I’m done. I have no interest in ever going out with him again.” Although he seemed very nice and normal, that was a deal breaker for me.


We stayed in touch on Facebook a little bit and a few days ago he called me and asked me some questions about dating after divorce. I decided to be honest with him and tell him without sugarcoating what I thought of his response to “Why did you get divorced?”


He then told me that he did not cheat on his wife, but rather that he flirted with some women, that it was inappropriate, and that he knew he handled things badly.


“Why didn’t you tell me that at the bar?” I asked.


Here is my point. How you answer, “Why did you get divorced?” is very important and can make or break a new relationship.


In this guy’s case, he is a total sweetheart. We had a long conversation and he admits he shouldn’t have done what he did, and that flirting and talking to other women is not a good way to handle a rough patch in a marriage. That he instead should have reached out to his wife and said, “You aren’t giving me what I need emotionally. I want this to work. I don’t want to lose what we have. Can we get help? Can we try to make our marriage better?”


If he’d have said those things to me at the bar, I’d have viewed him as he really is: a really good guy who made some mistakes, and actually, he didn’t’ even cheat. Maybe a tad bit of emotional cheating, but as a divorced woman, that wouldn’t stop me from dating him.


So, how do you answer, “Why did you get divorced?” First, have this answer prepared. I’m not saying rehearse it and be non-genuine. I’m just saying, really think about what you want to tell men (or women) about what happened in your marriage. If you know what you want to say, things will come out more smoothly.


Secondly, answer honestly. If you did cheat, you owe it to the person to say so. You can always follow up with how you regret it and what you now know you should have done instead.


Also, I want to add that you don’t have to go into tremendous details and air your dirty laundry about why you got divorced. Share as much as you feel comfortable sharing. But, make sure there is enough of an explanation so that the person knows who you are.


Lastly, don’t answer the question by talking about what an asshole or jerk or bitch your ex is. That just sounds classless and bitter. It’s unattractive.


Whether it’s in the first five minutes of a first date, several dates down the road or somewhere in between, the question will be asked, and how you answer it could be a game changer in the relationship, for better or for worse (no pun intended.)


How Do I Meet Someone After Divorce? The Answer: Start With YOU

Written by Jackie Pilossoph. Posted in dating, dating after divorce, Dating over 50


how do I meet someone after divorce


how do I meet someone after divorce







“How do I meet someone after divorce?” is a question I get asked almost on a daily basis. It inspires me that even after a bad marriage, men and women still crave happiness in this regard. However, what men and women don’t realize is, meeting someone isn’t dependent on how many dating sites you belong to, or how many blind dates you go on, but rather getting to know yourself, and what you really want and need. In this week’s Love Essentially column, published yesterday in Chicago Tribune Pioneer Press, I interview a relationship coach who helps people find Mr. (or Ms.) Right by helping them first discover themselves.

Relationship Coach Says Finding The One Starts With YOU  by Jackie Pilossoph


I can’t even count the number of single people who have said things to me like, “It’s so hard to meet someone,” “There are no good guys out there” or “I’m going to be alone forever.” It kind of makes finding Mr. or Ms. Right seem pretty hopeless, doesn’t it?

So when a friend of mine told me she was seeing a “relationship coach,” I was intrigued. I had plenty of questions for my friend. What does a relationship coach do? Help you set up your profile? Talk about where to meet single people? Tell you what to wear on a first date?

My friend’s answer: none of the above. Her Chicago-based relationship coach, Sue DeSanto, LCSW, offers a 3-month or a 6-month program that helps single, divorced or widowed men and women embrace their gifts and talents, and feel confident in sharing these with the world. In other words, according to DeSanto, being truly fulfilled in a romantic relationship starts with the person seeking rather than the person being sought.

I sat down with DeSanto to learn in more detail how she helps facilitate relationship opportunities. The first thing I found out is that nine years ago, she herself went through the program she now shares with her clients.

“I got divorced 14 years ago with two small children at the time, and found the dating world daunting and scary. I didn’t know how to do it,” said DeSanto, who holds a master’s degree in social work, and who has been a practicing psychotherapist for 20 years.
DeSanto attended the California-based Relationship Coaching Institute founded by relationship guru David Steele. Crediting the program for her success in finding true love and getting remarried a few years later, DeSanto decided she wanted to become a relationship coach herself.

DeSanto said her clients are successful professionals (like my friend) who want to find a partner. She said they feel frustrated and incompetent in their dating world, so they turn away from that part of their life and focus on work and career because that’s where they feel confident and safe.

“They feel invisible and not seen or heard in romantic relationships,” DeSanto said. “They are not able to see their own hidden blocks or barriers to having the life and love they want. I help them feel as confident and clear in their relationship life as they do in their work life.”

With weekly sessions either in person, via remote video chat or phone, along with homework, DeSanto said she helps clients first find their tools and strategies to determine their vision. In other words, figure out what they want, what they need and what their non-negotiables are.

The program includes…click here to read the rest of the article, published yesterday in Chicago Tribune Pioneer Press.


Coming Soon!



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