Should I Continue Seeing a Separated Man Whose Divorce is Nowhere in Sight?

Should I Continue Seeing a Separated Man Whose Divorce is Nowhere in Sight

It feels so good to have found you: your advice on your YouTube videos has felt like a soothing guide to my soul. 🙂

I am going on 4 months dating a man who has been legally separated for over 3 years. He asked me 2 weeks ago for a relationship, to be committed, exclusive, and only then, were we intimate for the first time last weekend. I mentioned how I feel about being intimate with a man who still has a dating profile up and last night I took mine down, told him, and he said he is doing the same. He has booked a trip for us to go away together for 5 days at the end of the month.

My question is, how do I navigate this issue of him being legally separated? On date 4, I asked what it takes to be divorced these days since I divorced 5 years ago and it only took me 3 months. He shared with me that he doesn’t want to be taken to the cleaners and that he doesn’t understand why he should have to give up 60% of his money. He does very well in finance. (On our 2nd date he confessed he still supports his ex who doesn’t work, and they have a 14-yr old daughter whom they both adopted at a later age in their marriage.) I have meditated on listening to my gut before continuing to date him and this feels good to me. I prayed internally on this before saying Yes to being in a relationship after he claimed me. I told him I don’t want to be a perpetual girlfriend, and that I want a loving, long-lasting relationship with one man and was keeping my options open until I found that… and that I do want to be a wife someday again, but want to do it right, not rush, and take time seeing where a relationship can go. He understood.  Yet, I never hear any news about him progressing with his divorce except for my asking him about it when he claimed me and I asked him if he is going through the proceedings at this moment, and he says, yes.

I want to give this relationship a try, not do online dating or any other, and would feel so happy and honored to have your guidance navigating through this situation.


Every relationship is a contract.

In every contract, both people have to agree to terms.

If you’re buying a house, you agree on a price.

If you’re taking a job, you agree on a salary.

If you’re entering a relationship, you agree on the nature of the relationship.

When you say, “I want to give this relationship a try,” or “I meditated, listened to my gut, and prayed internally,” you’ve apparently done everything except listen to what this guy is saying.

If you’re entering a relationship, you agree on the nature of the relationship.

He already told you how he feels about divorce.

He’s been separated for three years.

He doesn’t want to get divorced because he doesn’t want to give up 60% of his money.

The fact that you never hear any news about his divorce progressing is because his divorce is not progressing. He wants to date you. He doesn’t want to get taken to the cleaners in a divorce.

Next time around, trying listening to your man instead of listening to your gut.

Thus, you have two choices:

    1. Break up with him now before you’re too invested and find a man who wants to be your lawfully wedded husband.
    2. Stay with this man, fall deeper in love, and be perpetually dissatisfied that he never gets divorced (much less proposes to you).

Seems like a pretty clear-cut choice to me.

Next time around, trying listening to your man instead of listening to your gut.

Your man is telling you the truth. That’s more than I can say for your gut.

Join our conversation (30 Comments).
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  1. 1

    It is hard to make a judgement call here as more details are needed. Assuming his divorce has been filed, where do things stand? Is it in active litigation? Has there been a settlement or one in sight? Or is he simply ok being “separated” forever? These things make a difference. Besides, a person can never fully control the speed of his/her divorce. Not only it is a function of the court system and its backlog in any given county, but also it depends on how adversarial their ex is. And a very adversarial person can prolong things considerably, especially if it is beneficial to them in one way or another.

    I was in a situation where tables were turned. I dated a guy during my divorce, which from the date of separation to the date of the final divorce decree took almost exactly 2 years. My ex fought hard, and our fight sometimes turned dirty. While I wanted nothing more than to end any and all association with this person, I was also not about to walk away from a considerable amount of money that he owed me, but flat out refused to pay. So we litigated until the courts forced his hand. So, my boyfriend at the time was very concerned about it, and he was bringing that up. I explained very calmly that things with my ex were so over, we needed another word for over, BUT it was about my financial security and I was not about to compromise that. I am responsible for myself, no one else is. A few years later, the guy I was dating is history (and his concerns about my divorce and the uncertainty it created in his head was a part of why that relationship failed), and while I do miss him, I know I made the right decision. Since the money is still in the bank (or, rather, in the form of the downpayment on my new home). “Diamonds” are the girl’s best friends after all.

    All I am saying is, the OP needs to find out exactly where this divorce stands and where it is headed. You can’t hold one’s desire to secure their financial future against them. This is not about you.

  2. 2

    AHHHH…..Evan I wish this was printed four months ago. My gut DID tell me NOT to get involved with the man who was “separated” with three kids. After about six weeks, when I added up certain things he told me, I realized that he was still living with his (ex) wife. When confronted, he told me he didn’t “lie”, but rather “didn’t disclose”. Of course I pushed this red flag down


    Anyway, to make this short, you are right…I am going through the heartache now of him “dumping” me….when I am the prize here…I wish I listed to my gut, and then asked myself “WHAT WOULD EVAN SAY?”…he’s not the last man on earth, I can find the same qualities in another guy who is single, etc…GIRLS/…LISTEN TO EVAN! Ive been following him for 15 years…his advice is spot on

  3. 3
    Jill Jones

    This is very good advice, absolutely hits all the right points you should be paying attention to. Also, in this day and age when so many things are online I cannot imagine why more women don’t go online to validate things for themselves. The vast majority of counties have domestic relations records publicly available online ( they are called different things in different places but generally can be found via a county prothonotary’s office, civil litigation office etc. ). I’m a paralegal so maybe this is second nature to me,   but you owe it to   yourself to “trust, but verify”.    For divorce records   you won’t be able to see individual pleadings, like you can in general litigation matters, but you will be able to see the high-level docket –   when the matter was filed, when it was served on the other party, who the plaintiff and the defendant is, and generally what the status of the matter is (are they   going to mandated counseling, are they in the discovery of assets process, or are they almost at the end).   You can generally see who is filing motions and for what, and get a sense of who is dragging things out.   And of course the date the final decree is ordered and signed is also public record.   Viewing the docket is usually free, although in some places it may cost a nominal fee but it is still well worth the time and any money you spend   do you not have your time wasted or your emotions   trifled with.

    I can’t   tell you how many men I dated over the years who claimed to be separated or divorced (or that their divorce was further along than it really was)   and actually were not. Once I knew generally where they lived it was very easy to find out.

    Still, question your date to make sure you have the whole picture (you don’t need to let them know you checked them out; if they’re telling the truth they shouldn’t care, but some people are very private and get wiggy, even though they should respect your right to protect your interests).

    For example, one guy I dated checked out as divorce in process (he initiated). But what I didn’t know was that he and the wife, although technically separated & divorcing, the soon-to-be-ex was still living in the same house with him, a situation I was not comfortable with. I told him to call me when she moved out and/or divorce final).


    1. 3.1
      Yet Another Guy


      I was raked over the coals for the practice of “case searching” my date’s divorce records.   I avoid women who have been divorced multiple times as well as women who had messy divorces.   I have also discovered that women also lie about being divorced.

      1. 3.1.1

        you were also raked over the coals for calling me cheap.

    2. 3.2

      Jill says “….but some people are very private and get wiggy, even though they should respect your right to protect your interests).”


      It’s very understandable to me that they are getting “wiggy” at the idea of you snooping through their personal documents like that. I would be creeped out by that also. Especially if you say you spent money to snoop like that.   And nah, it’s not you using your “right to protect your interest”. It’s you being a bit paranoid and psycho.

      Just my humble opinion of course.


    3. 3.3

      amen Jill…for lack o a better phrasing, I am SO GLAD to hear I WAS NOT the only one this happened to…

  4. 4

    I personally, would never date anyone who is merely “separated” and I am surprised that anyone does– especially if what you want is a relationship.   In my book, separated means unavailable.   Available for casual dates (if that’s what you want), but certainly not for a relationship. Period.

    1. 4.1

      I agree 100%

    2. 4.2

      Yes, separated is a no no. At least a year should pass after divorce is final. I remember a guy on Match, who wrote me a nice message but he had “separated” as his status. I asked few questions and he has only moved out for a week from his wife and 3 kids. I wished him good luck and declined. He tried to convince me with bragging about his big house on the beach and a boat and what not. After few days I saw he changed his status to “divorced”… I bet women didn’t really want to go out with separated guy.

    3. 4.3

      I got online when I was going through my divorce and showed my status as separated.   The smart women refused immediately.   The nice ones explained why they were running the other way.   The crazy ones went out with me.

  5. 5

    Please allow me to add some personal experience to Evan’s advice.   Just because this man has “claimed you” doesn’t mean you are “his,” for God’s sake, so walk away!   You are clearly not his first priority.   I know a man who was legally separated for 10 years for financial reasons (and his hand was finally forced with disastrous results).   Also, men and women need space to heal and make a transition after divorce, and the first relationship after (or during) divorce is temporary.   And when he promises to step up the divorce proceedings when you tell him you are moving on, he will not, so do not change your mind.   Listen to Evan and hear what your man is really telling you.   You deserve better.

    1. 5.1

      thank you Ann…needed to see this in the bold you typed it in!

      1. 5.1.1

        I didn’t mean to type in bold – sorry, it looks like I’m yelling!

  6. 6



    I sympathise, because I’m in a similar situation, although there are significant differences. I’m seeing a man whose wife moved out in February, he has filed for divorce, and where they’re at is that they are trying to sort out the money issues. I won’t go into details, but the ex is asking for much more money than she is entitled to. He and I have been seeing each other for a few weeks; it’s not serious yet, but it’s getting there.


    In my case, the reason I’ve given him a chance is that he’s a wonderful man. Gorgeous and successful, but most of all he’s just incredibly respectful, gentle, caring and even-tempered. He treats me (and women in general it seems) like precious treasures, which I think is part of why he wound up in this situation with his ex-wife to begin with. I genuinely feel that he’s worth being given a chance.


    Having said that, there are signs that I have been watching out for from day one, and that I think are important to mention. In my guy’s case, he was the one who filed for divorce, he was the one who got his ex to move out, and he is the one pushing and trying very hard to get things resolved. In my book, that’s very important. He has told me (literally from our first date) that he is at a point in his career where, financially, he is able to and wants to enjoy life with his own family. He told me he was not looking for short-term dating but wanted a family again. He’s emotionally done with his wife and wants to put her behind him and move on with his life as soon as possible. He has told me this, and I can see that it is true, which is one reason why I don’t have the same insecurity about my relationship as you seem to have with yours, Juli.


    If the man is the one holding up the proceedings in the divorce, then that is a situation I would steer clear of. If he has not had enough time to grieve and emotionally move on, I also would steer clear. If there is a great deal of acrimony towards the ex and feelings of bitterness towards marriage in general, I would steer clear. I’d say also the degree of contact he has with his ex-wife is also potentially a red flag.


    Juli, what I would be worried about for you in your situation is you becoming like a comfort blanket for him. Someone there so he doesn’t have to be alone, so he doesn’t have to think about you dating other people, but with no solid, secure future. I’ve heard on this blog a few times of people in the US who don’t actually get divorced but stay separated indefinitely for financial reasons. I don’t quite understand it myself, but then again, the divorce laws may be much harsher than they are here. Divorce proceedings in the US also seem to take much longer than they do here. Once you reach agreement here in South Africa, getting a divorce is quick. Of course, reaching that agreement is what can be time-consuming. But staying married for financial reasons… that’s something I’ve never heard of here.


    So yeah, Juli, I think you need to get very clear with your guy on where he stands with the whole divorce thing. If he’s vague or cagey, I’d say that’s not a good sign. And even if he makes you promises, I’d say you need to set yourself a timeline to walk if he doesn’t follow through.

    1. 6.1

      Don’t you know, that in absolutely all divorces each party is sure that the other is asking for “more than they are entitled to”? Lol 😂 Just like prisons are filled with innocent people… so your guy wants to have a family and yet he kicked his ex out of the house and filed for a divorce? Sweetie I would be more worried about you than the OP. You can always learn about a person by seeing how they handle their divorce.

      1. 6.1.1



        No need to be worried about me, but thanks for your concern.


        I really didn’t want to provide details, but you’ve forced my hand by making assumptions. In my guy’s case, his ex-wife was the one who cheated. He was absolutely devastated about it. She had an ongoing affair with her boss, lied about it, and if that wasn’t bad enough, converted to Islam and started insisting that there be no bacon or alcohol in the house and asking him to convert too. Even with all that, they went to counselling and it took him two years to finally get her to move out. He just couldn’t take it any more.


        As for how he’s “handling” his divorce, if anything it’s made me respect him far more. He’s a wonderful father to his two daughters, and despite the fact that she was the one who cheated, he is fulfilling all his obligations to his daughters and to her, and will continue to do so. When I say she is asking for more than she is entitled to, I’m talking about exorbitant, extravagant amounts of money that she did not earn.


        And, yes, I do know how divorces go, so please cut the patronising tone. My own parents were divorced when I was six and the custody and maintenance battles ensued in a war-like fashion for years. I also worked in civil litigation. So I know what a bad divorce looks like and a good divorce look like. I also know what it looks like when one person is bitter and twisted and the other just wants to put it behind them.

        1. Marika

          I wouldn’t feel you have to justify yourself, Clare. I think it was clear you were sharing your experience in an effort to help the LW.

          Anyway, divorce is hard. No one can fully be prepared for what it’s like. Those of us who’ve been through it navigated it as best we could. No one can judge it externally.

        2. Clare



          Thanks for the support, and yes, I was trying to help the LW. I was trying to point out that there are nuances in these types of situations that I think often get lost when people are telling you to do this and that.


          As to divorces, I’ve seen it from both sides. My parents’ divorce was messy and awful, and they fought over my brother and I and money for years and years. My own divorce was incredibly civilized. We came to agreement quickly and were divorced within six weeks. We managed to stay on fairly good terms. Splitting up hurt like hell but neither of us tried to screw the other in any way. I even had a card for his bank account that he only asked for back two years after we got divorced.


          So yes, you’re absolutely right. No one can judge a divorce from the outside. It can depend so heavily on the circumstances and the people involved.

  7. 7
    Mrs Happy


    you clearly like him a lot and think this relationship has a future, so now you have to clarify what his desires and plans are.   So,

    1. bluntly ask him when/if he is planning to get divorced, and after that, ask whether he wants to remarry anyone once/if divorced, and then ask when he would see a 2nd marriage in his future. If you want kids, ask if he can father, or wants to have, kids.

    Listen to his answers. If those timelines or answers don’t suit you, leave.

    Lots of separated men have absolutely no plan to remarry again in the next 5 years, or even ever.

    2. It isn’t 60% of his money, it’s 60% of their money, thus the ex is only getting 10% of their wealth to raise a teenager.   Unless she can earn what he does, it’s actually a bad financial deal for her. They have a child together and kids cost a lot.

    3. Absolutely listen to Jill Jones at #3. In fact I’d hire her to do the search. There are yellow/orange flags here and you need objective clarification on the state of the so-called divorce proceedings.

    4. What’s with the “he claimed me” comments?   Have some backbone. It’s not the 19th century or a pirate ship.

    Best wishes.

    1. 7.1

      @Mrs Happy

      Personally, I would just leave, all these questions be damned. Sorry, but if a dude is not even ATTEMPTING to get a divorce and still financially supports his wife, the reasons he is doing so wouldn’t even matter to me. I don’t see why any marriage minded (or not) woman would settle for this foolishness. I see not one upside to this relationship.

  8. 8

    From the way he’s worried about his money, and dragging out the divorce, I don’t think he’ll ever even want to get married again.

    So, even if he does get divorced, there’s not telling if he’ll ever give her the relationship she wants.

  9. 9

    When I was single following a difficult divorce, I made a point of never dating a ‘separated’ man. If he’s not divorced, he is still married as far as I’m concerned. That means he is not free emotionally, legally or financially. Find someone who is, so that you can have the secure relationship you are looking for.

    1. 9.1

      amen to this

  10. 10

    This is not a black and white scenario. Legal status (separated/divorced) tells you exactly nothing about a person’s emotional status. I’m equally as suspicious of people who divorce quickly as of those who drag it out too long. This was meant to be the most important relationship of his life. Give him a break. At four months in, you barely know each other.

  11. 11


    I was in a situation like this. We wound up getting married and it worked out, but I’m not telling you this to get your hopes up. It was a long and at times painful road. It required complete honesty, communication and perseverance.

    My husband had been separated for three years from his ex. They had no children and she lived across the country. They split up initially because she had many affairs over the course of their 11 year marriage, even before they were married, and he had finally had enough. On top of that they were also very incompatible, nothing in common. They had grown civil to each other over the years and stayed together for the financial benefits, but they were living totally separate lives seeing other people.

    So when I met him for the first time, I almost walked away. It sounded like a bad situation. So if you want to do that in your own circumstance, I don’t blame you at all. It was tough for me knowing that there was unfinished business hanging over our heads. I chose to stay because we had the right connection and I wanted to give it a chance. I said to myself, “If this fails, it was my choice. I knew what I signed up for.” And I repeated that mantra a lot to myself for about a year before their divorce finalized and we could all move on.

    Even though it worked out for me, I wouldn’t recommend this situation to a lot of people. It was painful, it was drawn out and there was some drama between me and the ex at one point. There was a point when I almost walked away and he decided to make things right. That’s when I knew we were going to make it.

    The difference between your situation and mine is that your boyfriend is telling you straight up that he doesn’t want to leave his marriage. He doesn’t want to go through the financial and emotional trauma of a divorce, which there always is no matter how amicable it may seem.  In my case, my husband told me straight up that he did want to leave the marriage and he wanted a future with me, he just needed to cross a few hurdles first. But he was willing to take that step and he proved it to me when he took action. That was the key. Our relationship had a goal. It doesn’t sound like yours does. So if your goal is marriage, I suggest moving on because this man isn’t looking for the same thing.

    Evan is right: Its your call, just be aware of the terms that are agreed upon in the relationship from both sides. Be prepared to walk away at any time. Own your choices. Know what you’re worth. And no regrets. Peace.

  12. 12

    If you prayed internally then the answer to that prayer would be to pick up a Bible. Go to Exodus chapter 20, verse 14 and there is your answer.

    1. 12.1

      As for “listening to your gut”, you pick up that same Bible, turn it to Jeremiah, chapter 17, verse 19 and there is your answer.

      1. 12.1.1

        I mean verse 9

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