Should I Keep Dating A Separated Man Going Through a Divorce?

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

I get a lot of questions from readers wondering,  should I keep dating a separated man going through a divorce?  Here are two examples, the first one, a separated man who is frustrated because a woman doesn’t want to go out with him because of his status, and the second, a woman wondering if she should break it off with a separated man.


An online prospect won’t go out with me until my divorce is finalized…


I’m heading into the permanent separation stage with the outcome being divorce. I have been married for 27 years and have two grown children. The last 10 years have been absolute misery. I hung in so my kids could launch. I am now setting the stage for my new life. The problem is this; I met someone online and we really connected. However, she does not want to proceed until my divorce is finalized. That could take 2 years! Should I forget about her or text her from time to time?


I know that he will still need to go through a period of mourning, especially once things become more finalized with his divorce…


I’m a 27 year old woman dating a separated man going through a divorce. A quick background: I met him about a year ago through work. We became fast friends, bonding through shared interests. I knew he was married with two young girls, but had no idea he was going through a separation, until he finally told me the situation had been going on for almost 2 years.

We remained platonic for about 5 months but over time we’ve eventually evolved into something more.  I realize that this situation is difficult, especially since the marriage is not officially over. I know that he will still need to go through a period of mourning, especially once things become more finalized with his divorce.

I would like to know, from your perspective, if this is a period that I should be around for, or if it’s something that he needs to go through alone? Despite the fact that our relationship became more than just friends, we both pride our relationship on the fact that our friendship is the most important thing to us both. Do you think that returning to a platonic friendship now would benefit us – potentially allowing for a long-term relationship in the future? 


Here are my thoughts on dating a separated man going through a divorce, something I’ve done twice.


When people begin dating after divorce, they have certain criteria, conditions, and qualities they are looking for, which are probably continually changing. They are flexible with some of the criteria/qualities, such as, “I really want him to be over 6 feet, but if he isn’t I might be OK with it,” but other things are 100% musts. In other words, they are deal breakers.


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One of these musts/deal breakers for a lot of people is, “He/she MUST be officially divorced.” Maybe they fear that the person hasn’t grieved the divorce, or hasn’t been alone long enough, or maybe they think there’s still a chance he/she might get back together with the ex. Or, maybe they think think he’s just covering up his pain with a Band-aid, the Band-aid being a new girlfriend. In any case, they have their reasons for being opposed to dating a  separated man going through a divorce.

Here’s how I feel. The decision to separate takes time. A couple doesn’t  just decide one day that they want to get separated. In most cases, they have been unhappy for months, years, even decades. They might have subconsciously ignored the red flags, tried to just grin and bear it, and not want to face the fact that the relationship was falling apart.

So, they did nothing. Then you have the couple where one person cheats and they decide to separate. That is the only instance I can think of where a couple would just decide to separate overnight. That said, the cheating probably happened because one or both people weren’t happy in the marriage, so again, the decision to separate wasn’t really an overnight decision.


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Then, getting divorced takes time. You don’t decide to move forward with a divorce, go to court the next week and then sign the papers the week after. The divorce process can take months, even years, because it is a very very complicated, rollercoaster process where emotions and children and finances collide.


The point I’m trying to make is, if someone decides to start dating when they are not officially divorced, no one should judge them. Chances are, they have spent years unhappy, feeling lonely, knowing the marriage was over, and grieving it. So, really, they could be divorced (emotionally) but the process just takes awhile.


My criteria for dating a separated man going through a divorce was never “is he officially divorced yet?” but rather:

“Does he seem emotionally ready for a relationship?”

“Is he truly accepting his marriage is over?”

“Does he have hopes of getting back with his ex?”

“Does he seem checked out of the marriage—i.e. not talking about it every second?”

“Is he using a girlfriend as a quick fix for getting over his divorce?”

“Does he have no intention of getting divorced and is he just telling people he’s separated?”

“Is he considering divorce and just playing the field?”



Those questions are more important than a piece of paper showing that your divorce is final (in my opinion.)


I will say this. Dating a separated man going through a divorce could blow up in your face. It blew up in mine once.

I dated someone who was separated for several years. “We just haven’t gotten around to finalizing the divorce,” he would say. When his wife decided to get married, all of a sudden, the divorce became final very quickly. I found out years later that he cheated on me with her for a long time. It hurt like hell. I realized that he always kept the door open to getting back with his wife until she remarried. He then wanted to marry me. It was the worst feeling in the world to realize that.

Now, all that said, guess what? A guy who is officially divorced could be that way, too!


A divorce decree does not mean someone is ready to date, and not having a divorce decree yet does not mean someone isn’t ready to date.

In closing, dating a separated man going through a divorce might fee risky to some. I say dating a guy who isn’t emotionally ready to date—divorce decree in hand or not, is risky.

Every person and every divorce and every relationship is different. No one should judge or tell anyone what to do, because they don’t know the whole story. But, I will say, if they swipe left because the guy isn’t officially divorced, they could be missing out on something really great.

Like this article? Check out, “Dating after divorce: Why This is an Exciting Time!”


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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. 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.

5 Responses to “Should I Keep Dating A Separated Man Going Through a Divorce?”

  1. Christie V

    This is a GREAT article. I tried dating before my divorce was over and it didn’t really go well, but everyone is different. I also decided not to date anyone who is not yet divorced either but this article gives me a new perspective!

  2. Susan M Feller

    Stay away until they are completely divorced . You really dont know the whole truth. You could be getting in the way of reconciliation. To many home wreckers. It could be absolutely devastating to the spouse and they are human you could be causing unnecessary anguish. Just wait and ask around do a background check. People that leave whether their miserable or not will go after the new excitement and not take responsibility for the hardships of marriage. Toss out the old model for a new one. No integrity these days. I sure wouldn’t want to be the rebound person anyway.

  3. Byron

    Every situation and ever person involved in them is different, may we all have the grace not to judge them.

    Having said that, and as hard as it was, “getting off the Merry-Go-Round” not just until the divorce was final, but until I could stop venting about it in every conversation I had – was probably the best thing I could have done for myself and the kids. But we’re all different. I don’t at all regret that 35-month journey of healing and self-rediscovery. Freed from the chaos and animosity of divorce, it’s been so much easier maintaining a long-term and stable relationship afterward. Some of us will make a relationship during a separation work. Some of us will write a new page in our life’s book of missteps. Some of us will avoid it altogether.


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