The Painful Downside of Dating a Separated Man

Are you dating a separated man? You face a lot of potential issues when dating a man who is not done with his divorce. Find out why this might not be your best strategy to find true love.

dating a separated man, understanding menThe Inside Scoop on Dating a Separated Man

So, you met a man online who is really cute and a lot of fun. Yeah – finally. He seems into you and ready to spend time together. You text, talk on the phone and go out on dates. So far so good.

He’s not divorced yet, but what the heck right? He’s not living with his wife any more so that’s a good thing.

Then something shifts. He starts to have less time for you. Maybe he reveals some of the struggles from his on-going divorce. His schedule with his kids isn’t settled yet. He has court dates. His job is stressful. He’s fighting with his not yet ex. His children act out. Wow – there’s a lot going on.

And all of this stuff takes its toll on YOU!

See, the inside scoop on dating a separated man is that he is not divorced yet. That means he is STILL MARRIED.

Divorce Is Hard

I realize this is stating the obvious, but in most cases, divorce is extremely difficult. There are so many things that need to be worked out like:

  • Finances
  • Custody
  • Visitation
  • Division of Property
  • Child support
  • Alimony

In addition, divorce has a massive emotional component. Breaking up is rarely easy no matter what the reason. So it’s hard to heal until everything has been completed and the dust settles. Therapists agree that can take a minimum of one year and often longer.

So dating a separated man opens you to havoc and strife. He’s not ready for a true relationship. His heart is not healed or available. He has so much to figure out, work out and go through. How can he be the loving, supportive, fun guy you dream of with all this weighing him down?

The simple answer is HE CAN’T!

The Drawbacks of Men Who Aren’t Divorced Yet

  1. They don’t know what they want
  2. They are not emotionally available
  3. They are confused about romance and relationships
  4. They have not healed the wounds of their current relationship
  5. They aren’t ready for a serious relationship
  6. They might just want emotional support, sex or ego boosting
  7. They are still connected to their ex, even if they hate her
  8. They are often embroiled in a difficult struggle
  9. They are smothered in loads of drama
  10. They might want your help to get through it, but then they’ll move on

Given this list (which doesn’t cover every possibility) does it sound to you like dating a separated man is a good idea? DON’T DO IT!

If you are looking for lasting love and a long-term relationship, a separated man is a very poor choice. This is true no matter who he is or how good it COULD BE. You are not dating a man’s potential.

You are dating him with all his problems and warts. And you will be exposed to his pain and drama and will not remain untouched or above it all. No way. You ‘ll be sucked in and sucked down in the vortex of drama along with him.

Looking for True Love? Date Men Who Are Available

If a lasting, loving relationship is your main objective, you need to find a man who is relationship ready. He needs to be healed from divorce or breakups. He needs to be divorced for at least one year if not longer so time has passed and the emotional dust has settled.

Do NOT date men who cannot meet this basic criteria. If you do, you are boldly CHOOSING drama and pain. You deserve better. You deserve to be with a good man who wants what you want. Being in alignment regarding your dating agenda gives you a solid foundation to build on. It won’t always work out, but your chances are about a thousand times better.

It’s not that he isn’t a good person – he might be wonderful. Just not right now. Don’t think he’ll get better while you are dating him. You might be his transitional woman, but he won’t likely see you as “The One”. You might be “The One” who helped him get through the divorce, but most often you’ll be abandoned.

That’s why my dating advice is loud and clear – don’t start dating a separated man.


Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

25 thoughts on “The Painful Downside of Dating a Separated Man”

  1. I have been dating a guy who is separated and they live apart. He has a 3year old and is a fantastic father. He is always worried that if the mother knows about me she won’t let him see the child. He says he would like to introduce me to the child and his family next year after we have been together for a year. Now he has been distant for a few days after he spent the night with the ex’s family and their daughter. I told him it made me uncomfortable and it crosses boundaries. He didn’t argue but we haven’t spoken on the phone in 2days since. Just what’s app messages. Is it time to let go? I spoke to a counselor because I wanted clarity. She said nothing his done prior to this raises any red flags.

    • Hi Smiley, This is a perfect example of why I recommend NOT to date men who are not yet divorced. He’s not over her and spending time with her! To me, he’s not at all ready for a relationship and his pulling away demonstrates that clearly. He’s not emotionally available. If you want to avoid heartbreak, I know this is hard, but my advice is to move on to find a man who is relationship ready and is single or finished with divorce, maybe for a full year – that is the best. The last thing you want to do is “nurse” a man back to emotional health because they tend to leave and find a new woman to marry once they feel better.

  2. I started dating a man who has been separated and living apart from his wife for six years. I have been widowed for 9 years. He says he likes me and wants to take things slow. He and his wife have decided to be respectful and polite to one another. They have three children 25, 22 and 16. I have one 16 year old. This man is very sweet and kind to me. He keeps our plans and contacts me throughout the day. Should I continue on this journey? I have started to have real heartfelt feelings for him.

    • How can I say what you should do Shoshanah? Taking things slowly often means a man is not serious minded about finding the right relationship. But if you enjoy his company and see him as often as you want and he treats you well, it could work. But if you want to marry again, he’s not the guy – at least not now since he is still married…

  3. Im having a hard time.. my boyfriend is still married but separated from his wife.we have been living together for about 5 months. I left my country to be with him. He always showed me he loved me. He always tells me he loves me. He has never made me feel worthless. We always talk about having a family getting married and have a future with me. I went back to my country for two weeks to visit family. We were talking on the phone.But out of nowhere he said he had a dream about his wife and his daughter and that he is confused… idk what to do

    • Hi Jasmine, I know this is incredibly hard. But, there is literally NOTHING you can do. This is HIS journey and he is demonstrating the very reason why I strongly urge women not to get involved with separated men. They are not emotionally free or truly available. So this isn’t about whether or not he loves you. It’s about his capacity to love you freely when he is STILL attached to his wife. SHE’S NOT HIS EX – that is the problem. The only leverage you have is to not return and tell him to figure out what he wants and let you know when he’s ready to get divorced and focus on you. When he has a court date for divorce – then its far more real. But it’s still best to wait for a year after a divorce is final before dating a man. Ultimately, I’m not sure what will happen here, but the last thing you want is to invest more time and your heart in a man who is not sure of what or who he wants.

  4. Really interesting article! I am in a relationship with a separated man now for 8 months. I’m 34 and he is 46. He is separated from his ex wife now for a little bit over a year. His problem is that he is confused, on one hand he wants to have a woman in his life, he is even open to marry again. But on the other side he tells me he is scared and so on. He even told me he loves me, but is just not ready to commit…I don’t know what to do. Should I wait another year? Should I tell him, if he wont commit to me I will leave ? Should I give him an ultimatum? With divorce he is currently still separated, but is willing to finalize his divorce in the near future. He knows that is bothering me. Thank you for your advice! [See the full question and my answer on this post]

  5. Hi, my husband of over 20 years left me and our children to be with another woman who he says is nice to him. He has only been with her for about 2 months and as far as I know they have not had any sexual relations. I know that he is still in love with me because he said he is and says he always will. the main reason he left is because I was going crook on him a fair bit and he was sick of it and not because of this other woman. We still do things together with our children and we always cuddle whenever we see each other. This other woman doesn’t like my husband drinking, but he won’t stop for anyone. He has depression and I think I maybe the cause of this. He seems to think that I don’t love him anymore. But I’ve always told him I do. It’s really complicated and there is too much detail to put here. He did tell my daughter that he’d be back when he was ready. He seems to be so confused as to what and who he wants. Any advice?

    • I mean you no offense but how can you believe he hasn’t slept with this other woman he left you for? This man LEFT you and your children. So I wouldn’t cuddle with him making his leaving seem OK with you. And why does he think you do cuddle with him if it isn’t love? Now maybe you were being too difficult to handle and showing too much anger, so my advice is to work on that yourself. But over all it seems to me like he wants you both and if you are not OK with that, let him go. You don’t have to be mean to him, but you don’t have to offer him wifely duties of any kind. And if after everything you do want him back, suggest couples’ counseling. If he won’t go- he doesn’t really want to come back.

  6. I’m in a difficult position, I am scared I might be the transitional woman for the man I am seeing who is technically separated. He’s told me everything any woman would want to hear. I’m the one for him etc etc. I explained to him what my concern is and he says he finds it hard to believe that will happen. Whereas I’m a little more paranoid about it. I’m going to kick my self hard if down the track he ends up leaving me after I stuck by him because he “reassured” me that I am who he wants to be with. Stuck between the pain of letting him go and telling him to find me when the time is right (which could be a long time)…or sticking by him still now, but then possibly finding out that he doesn’t end up needing or wanting me anymore as I may fit the transitional description…. such a crap situation to be in.

    • Hey Worried, The truth is life is a crap shoot. You never know what will happen so you make the best decisions you can with the info you have. I recommend avoiding relationships with separated men for this reason. However, if he’s good to you and you don’t put up with a lot from his ex, then staying might not be such a bad idea.

      If you aren’t hoping to have a family soon and need to marry, why not just relax and enjoy each other? You are already in it. There are never any guarantees in life, career or love. Any man could leave – not just this guy. So, my advice is to enjoy what you have and stop the “what ifs” and driving yourself crazy. If it ends, you’ll find another.

  7. I know this is an old thread but I have been reading some stuff online and would like some advice or perspective. I have been amicably divorced for 5 years. I have dated a little but not much. For the last few months, I have been talking to a man (we are in our 40’s) whose wife of 15 years came out to him a couple years ago and began seeing another woman. Because she is afraid to publicly come out to her family, her girlfriend is just considered her BFF to outsiders. For now, it appears she is calling the shots. She is reluctant to file for divorce for fear that she will upset her family. And I suspect for financial reasons. He told me that she knows about me and that he knows that if she had cheated with or seeing another man, they might already be divorced. I know I’m only hearing his side of the story, but some of what he has said I have confirmed myself and it appears she is holding him hostage. He has been very open with me from the beginning, doesn’t get defensive and answers any questions I have about their situation. They have a 12 year old daughter so custody would be involved. How long should I wait before something is filed or a move is made? What should I look out for? Is it possible this could work out?

    • Hi Regina, My advice to you is to get out now. Why would you want to put yourself through this ugly divorce? That’s why the post is about now dating separated men – divorce is so hard and this isn’t even your divorce. Worse still he’s not even in the process of getting divorced. So you are looking at years of torture. Why wait at all – just go meet a man who is emotionally available and ready for a relationship. This man is actually NOT available and even if he is a really nice guy chances are strong this will end in heartbreak and tons of lost time. I would rather see you avoid that – don’t you think?

  8. Great article. Wish I had read this (and the dozens of other articles online giving similar advice) before I started dating a separated man (who had his heart broken by his wife of over 20 years who was having an affair). I have a better understanding now of why it’s a bad idea to get involved in the first place and the reasons why they are not ready for a serious relationship while they are going through the first year after a difficult separation. But I guess what I’m struggling to understand about “transitional” relationships is: If the relationship with the “transitional” person is going well, why wouldn’t they choose to continue and gradually progress to a more serious relationship as they are beginning to heal rather than “moving on”? I realize all relationships are different, but it seems that the consensus on “transitional” relationships is that it is “most often” the case that they will not see the transitional person as “the one”, and I just don’t quite understand why that is typically the outcome of these relationships.

    • Hi Jessie,
      Who can really say. But my one thought on why a man wouldn’t continue is that he was into you as you helped him recover. Then he lost interest as his neediness declined. When he feels more like himself again and has recovered, he looks at you, remembers how far he has come and wants a clean slate. He finds a new woman who didn’t see him at his weak point and doesn’t remind him of that time. So he moves on. Does that make more sense?
      Sometimes understanding is not always available, but that doesn’t change the truth of the situation.

  9. Can you advise on dating a man who’s wife died from cancer. I am dating a man (for 3 months) who’s wife died just over a year ago after a 40yr marriage, he is always putting me first when making plans, holds my hand and hugs and kisses me in public, he works week days and we spend every weekend together, and sometimes go for lunch together during the week, he has introduced me to his friends and family as his girlfriend (after asking me if that is okay) has told me I am the best thing that has happened to him, he loves me and is committed to me and yes we do have a really great sexual relationship (we waited a month) as well. The problem is he quite often keeps talking about and bringing up things that his wife did or said. I told him I did not want to be compared to his wife and he totally accepted that and said he doesn’t and wouldn’t. But him talking about her does make me feel uncomfortable, so how do I deal with it? I am falling in love with him. As you may have guessed we are both in our Sixties.

    • Ngaire,

      When a man or woman has spent 40 years with someone, that doesn’t disappear. Even someone who has healed completely will have memories to share occasionally. I don’t know if he brings her up multiple times when you see him or once in a while. If it’s not every time, I would try to live with it. He’s a great guy and loves you. She’s gone and you are with him now.

      If he brings her up constantly and you can’t handle it, there’s not much more you can do. You brought it to his attention and he’s probably trying to be aware of it. But like I said, it’s pretty difficult to erase 40 years with another woman. Only time does that. You can give him the time and be patient or leave. But those are the only alternatives. If you turn this into a huge deal, I can’t see how you’ll win. You can occasionally remind him very gently that you rather talk about something else.

      I advise you to think big picture. What percentage of the time does he talk about his deceased wife and what percentage of your time together is wonderful? Then decide what you want to do.

    • Kristin, sometimes people have experiences that they learn from and become wiser. Now that you know, good for you for deciding never to do that again! Wishing you love, Ronnie

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