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

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

I get a lot of questions from readers wondering,  should I keep dating a separated man going through a divorce?  I thought I’d help shed some light with two examples of people in this scenario. The first one, a separated man who is frustrated because a woman doesn’t want to go out with him because of his status (he’s not officially divorced) and the second, a divorced woman wondering if she should break it off with a separated man, whose divorce isn’t going to be official any time soon.


“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 children 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?


Michele Heffron, Divorce Coach, Life Strategist


“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? 


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Online Dating Coach and Stylist


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 tall, 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. Or, there is an act of abuse that takes place. These are instances where a couple might decide to separate overnight. But even in these cases,  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. As far as the abuse, maybe the person never went this far, and now the spouse knows there’s no going back. Again, it wasn’t an overnight decision.


Joanne Litman - Eagle Strategies LLC - Financial Solutions for Women


The thing is, 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, roller coaster 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. Dating can be an attempt to move on, to break away from the marriage. That can be healthy–as long as the person doesn’t use their new partner as the solution to all their problems.


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?”


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These 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!


Nix Baker Wellness and Therapy


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

    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:

    8 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.

    4. Beth

      Totally agree regarding just because a man/woman has finalized their divorce they are ready to date. I dated a man who was divorced 3 years. He was still in love with his ex wife who was about to get engaged to another man! This former paramour of mine was obviously not ready for a relationship! Unfortunately, it takes time to figure this out.
      Sometimes ppl are still separated because the divorce is heavily litigated through no fault of their own. Their soon-to-be former spouse won’t let it go and settle. This could go on for years! But this person is whole-heartedly ready to date.
      Great article because it is not so simply cut and dry as to whether or not to date a separated man or woman. One needs to consider many factors. I whole heartedly agree with Jackie on this one.

    5. Melanie

      I am recently divorced. My ex has a Gf while I remain unattached until I am ready to put energy into dating. I have been interested a few men, but there is no rush to get into something so soon. I dated a couple of divorced men before I met my ex, and both of them held resentment toward their ex wives even after one had been divorced for four years.
      I think dating after divorce is completely different than dating before you get married the first time. When someone is unable or unwilling to be alone for at least a year, that is a red flag to me of being replaceable quite quickly.

      • Beth

        It can also mean that they are an avoidant personality, the absolute worst type to date.
        It’s such a delicate balance. Nothing is cut and dry. One just has to be aware and ask a lot of questions to determine if your date is ready to date again. Agreed, that expression of resentment of an ex spouse is a huge red flag.


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