I Am Falling In Love With a Man Who Is Finalizing His Divorce. Should I Back Off or Can This Work Out?

Hi Evan,


Your blog has been really helpful as I find myself in an interesting situation. I’m 44, divorced with a son in college. Been divorced for a long time. Met someone at work and became friends over the course of 4 years. He’s been separated from his wife of 34 years for the past nearly 2 years. I didn’t realize he was interested in me as more than friends for at least 2 years, but found out 2 months ago. We started dating, held off on sex until last month, but he told me last night that he came to the realization that he’s not sorted through his emotions like he thought he had.


He still wants to see me, doesn’t want to pull away, but also doesn’t want to hurt me because he’s not sure what this will entail. He’s scared, has not felt this way before, and doesn’t know what is next. The divorce will be final within the next 2 months and I think it just really hit him, thought he thought he was doing fine. We get along amazingly well, laugh together, really care about each other and can talk to each other about anything. I’m not sure if I should step back even though he doesn’t want to, and let him work this through. Is there a chance it can work out? I think we can have something really special together. He’s as in touch with his feelings as a man can get, I think, so hopefully he can work through this and move on, hopefully with me. Any suggestions?




Dear Sunshine,

You’ve got to ask yourself one question: “Do I feel lucky? Well, do ya?”

Lots of women say they want the truth; few of them know what to do when they receive it.

Because this isn’t a matter about which I can give you any reassurance. All we can do is look at the facts objectively, and then assess your tolerance for risk.

The good news is that you’re with an excellent communicator. He has feelings for you, but has openly expressed his reservations as well. Apart from him declaring his blind love and devotion, you can’t ask for much more than that. Really. Lots of women say they want the truth; few of them know what to do when they receive it.

I know this from first-hand experience. Women always want to know what men are thinking, yet when we let you into our thought process, you immediately find fault – basically because we think things that you wouldn’t want to hear. That’s why we usually don’t say them.

“Yes, I’m attracted to other women.”

“No, I’m not positive humans are biologically programmed for monogamy.”

“Yes, I’m having reasonable doubts about whether we’re meant to be as a couple.”

These are perfectly fair thoughts that men usually don’t express, to protect you. Then again, just because we have a thought doesn’t mean that we don’t have equally contradictory thoughts.

“I’m very attracted to you.”

“I do see the benefits of monogamy, especially in raising a close nuclear family.”

“I may be having doubts, but I’ve yet to find a partner who makes me as happy as you.”

Clearly, I have some experience in this realm, and, as always, my wife is the exception to the rule. She had been burned before, by a cheating husband. And all she ever asked was to know exactly where she stood – even when it wasn’t what she wanted to hear. So when I openly expressed my reservations that I wasn’t “feeling what I thought I should be feeling”…she didn’t panic. She took it in and let me process. I proposed to her two weeks later and am EXTREMELY happy that I did.

Because you have clarity, you think it should be equally obvious for your partner. Alas, it’s not so simple.

To bring it back to you, Sunshine, your guy is in a position that millions of divorcees confront as they’re getting back out into the dating market. He likes you, he’s attracted to you, he desires a long-term relationship…but just doesn’t know if he’s ready to dive in again. He’s lonely. He’s made mistakes before. He wants to look before he leaps. But he just can’t help himself when he’s around you.

As such, he’s genuinely conflicted. And that’s the hardest part to deal with when you’re not conflicted. Because you have clarity, you think it should be equally obvious for your partner. Alas, it’s not so simple.

Be thankful that you have a man who respects you enough to speak his mind, be cautious that his reservations are legitimate, and be respectful of the fact that his process might be trickier than your process.

All I can say is that I guarantee that you will definitely not fall in love if you cut him off out of fear; you at least have a chance if you let him come to his own conclusions.

At least that’s what my wife thinks.

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  1. 61

    #60 Brenda

    Totally agree!  No one really who is recently separated is in the right state of mind to start a REAL new relationship, they haven’t processed the old relationship yet, and that takes time.  I think that we BELIEVE we are ready (and I am included in that!)…

    I dated a man who was divorced twice and his therapist told him it’s an average of 3 years for a man to ‘recover’ from a divorce.  Some never do…

  2. 62

    I should have found this thread about eight years ago.
    Because I briefly lived in an area where people married young — and divorced young — I was totally unprepared when I dated a recently divorced man. He was 33, I was 25 and because of my relative youth and naivete, I believed everything he said about being over his ex-wife.
    They had “only” been married four years, there were no kids, he talked about how much healthier he was emotionally… I fell for him and although we didn’t date long, he began to waver when I said I was looking for a long-term relationship.
    Suddenly, he was forced to recognize that he wasn’t ready for another long-term relationship like he thought he was. He said I had done nothing wrong and that my behavior and expectations were perfectly normal for a girlfriend, but he wasn’t ready to be a boyfriend.
    He still wanted to maintain a friendship though, and I went along with it for about a month until I realized that it was all to be on HIS terms. He’d see me when he was lonely/bored/needing company, but wouldn’t do the same for me. He’d call when HE felt like it, not when he promised to. That was boyfriend/girlfriend stuff (calling at the time he said he’d call), and I’d been demoted to “friend” who had to understand that he was busy and would call whenever he decided to.
    No, he didn’t state it that bluntly, but I remember this was a man who was never late for dates, who would apologize if he called 15 minutes after the time he said he would call me, who would call me in the car driving to work or meet me for breakfast when we were dating… suddenly it was, “Oh, you’re my friend, and my other friends understand that I get busy.”
    I did myself a big favor and cut off all communication. Best thing I ever did.
    But I then started to wonder if I had some kind of Recently Divorced/Separated Man magnet on my forehead because they kept coming. And I wasn’t even in the traditional age range in which I’d expect to meet a lot of men coming out of marriages.
    I really grew to despise these men because they were all the same. I fell for the game one more time — partially because I listened to women who kept saying that I was being too hasty and that I should give these men a chance, and each time, my suspicions proved correct.
    After that, no man who had been divorced for less than a year got a second date from me. Definitely no separated men. And if they asked me why, I told them the truth… “You have no business trying to date anyone right now. You are recently divorced, you have no idea what you want and the last thing you need to do is try to get in another relationship.”
    Yes, it might have been mean and reflective of my own past hurts, but at that time, I didn’t care. I felt like no one ever called these men out on their mess and even if it didn’t change them one bit with another woman, at least they knew exactly how I read them. A few came back and told me years later that I was absolutely right.

  3. 63

    I met one online too, said he was single. In our first phone chat i asked how long hed been divorced and the answer was 6 years.
    Two months later I am walking in my closest friends garden with them and him , and friend says , “How long have you been divorced?” he says ” Separated for 6 years now , not actually divorced” . I tripped over a hay bale !
    I lost my sexy REAL quick . See he was conflicted , still caught up in the domestic fairytale he had in his marriage , its demise , and the reasons he had never addressed , but really WANTED me to fix all that for him. After pinning him down about the lack of divorce he assured me he would work on it next time he was in his home country but it was tricky due to the financial declarations needed , huh ??
    Turned out he also owed his Government hundreds of thousands of dollars…DELETE !
    I did however learn to ask the question up front and eye to eye , Are you divorced? How long since ? hows youir relationship with the ex? etc..
    I wont date a married man until the divorce , and that means a year of separation by law here . It also means any one still sharing homes with the ex is a definite NO WAY for me.

  4. 64

    Hello All,

    It’s been intersting reading about your dilemmas with seperated men.  I too am going through a similar situation.  I was dating a seperated man for the last year.  It started out as friends, soon turned to what we jokingly called friends with benefits.  We were both going through a hard time, and my loneliness allowed me to get involved with him, even though I saw all the red flags, and found out so many after we started sleeping together, like his horrible financial situation, wife problems etc.  And the benefits were weren’t that great for me. 

    So, I was desperate for companionship, I realize this and so was he.  I tried to fix him, waste of my time, I know, and he certainly didn’t like to hear the truth from me about his irresponsibilites etc (he’s not young, in his late 50’s).  But, we hung in there and as a woman, my heart got more attached even though I know he isn’t life partner material, but unfortunatley the heart still gets attached, of course there were many good things and good times too. 

    Recently, I told him I don’t want to be a FWB, and I want more.  I would have even settled for an I love you, but he thinks that would complicate things, ha!  So, I realized after 9 months of being intimately involved that I was getting too involved and would be in trouble if I continued.  Now, I’m dealing with the grieving of that decision.  I don;t impagine any one of you would disagree with my decision, but it’s still hard to process. 

    However, I also wanted to share a success story that happened to one of my friends (not a friend of a friend), a real life tale and I hope Casey reads this too.  By the way, Casey, I do feel for you, it’s hard to beleive in what seems like a miracle (guy will come back) and I doubt it too, perhaps even harder when you’ve been intimate (although you would think it shouldn’t be so) 

    Anyways, my friend,  met a man, a very good catch I might add, who was interested in her and was going through a divorce.  She told him that she will not date him until he is fully divorced.  They proceeded to be friends and he did not see other women.  He told her she was worth the wait (music to our ears).  They were friends for 9 months, hung out a lot, lauged alot (not even a kiss was exchanged in that time).  After nine months when he divorce was complete, they started dating and got married two years later!! 

    She said to me “When he told me I was worth it, it told me a lot about his character”.  I love the story and I love my friend who must have had such amazing confidence to be able to stick to her guns.  She had been hurt before too, but how many times do we really change? 

  5. 65
    Vina Guardado

    Oh my goodness! a tremendous article dude. Thanks Nonetheless I am experiencing issue with ur rss . Don’t know why Unable to subscribe to it. Is there anyone getting identical rss downside? Anyone who knows kindly respond. Thnkx

  6. 66

    I’m in a similar situation with a twist. Eight years ago I had a breakup with a man who was the love of my life. It was an amicable breakup: we just couldn’t get over one huge difference. I wanted children, he didn’t. It was an insurmountable problem, so we parted, very sad, very much in love but knowing there was no way round this. We stayed friends and several months later he met someone else and married her in under a year. We stayed in touch – talking maybe half a dozen times a year on the phone and seeing each other for coffee maybe once or twice a year. Now, they’re getting divorced. It’s ugly, messy, she came home a month ago and demanded a divorce, hundreds of thousands of dollars etc. and the car. The marriage was always bad it seems – they slept in separate rooms within a year of getting married. She never worked, he spent a ton of money on her and now she’s getting nasty and trying to take everything. He called me when this all fell apart and we’ve spent a LOT of time together. I see him two to three times a week – sometimes just for coffee, sometimes we just chat about anything but her. We also talk on the phone every day and email. But he’s a wreck right now and I’m not sure if he just sees me as a helpful friend – a shoulder to lean on during these tough times. For me, all those feelings from 8 years ago are back with a vengeance. I am still deeply in love with him and I thought I was over him. Clearly I’m not. Given his awful marriage (she got a Green Card through him) and divorce he may swear off women forever. We have always been open and honest with each other and we’ve come back to spending time together and connecting in the same way we did 8 years ago. Now, I can’t have children anyway so the kid thing is moot. But I no longer know if he still has those kind of feelings for me that I have for him or if he just sees me as a friend he can trust. I don’t want to abandon him right now but I also don’t want to get invested in him again if he doesn’t have any feelings beyond platonic ones left for me. Maybe he’s spending time with me and those feelings are coming back to him (although he’s in no place to act on them and neither would I right now). But I wish I knew if he were thinking about me as more than a friend even if he’s clearly not ready to act on it yet. I want to be there for him but I also want to protect myself. If I landed up being hurt by the same person twice by discovering he just doesn’t feel “that” way about me anymore even I wouldn’t have any sympathy for me! I have no idea what to do.

  7. 67

    It is a mistake to think in terms of amount of time. The last guy I dated had been separated for two years. We dated for four. That was two years ago. He is STILL married!! Not that they are not really separated it’s just they can’t come to a settlement. He said he left his wife because she became addicted to video games and wouldn’t work or clean house anymore. After dating me and some other woman, he finally came to the realization that she might have become depressed because he was too critical, thereby turning to video games to escape.  So he started trying to work on being less critical with me, but still didn’t want to commit in any way shape or form. Oh, keep that in mind if the divorced man in a long term marriage complains his wife changed for the worse somehow, the man may have influenced it. But that is off topic slightly. Anyway..yes they will date but who wouldn’t be commitment shy after a bad marriage they are still struggling to get out of?

  8. 68

    I am in exactly the same situation.  I met a man online who is separated.  We casually dated for 3 months and around month 4 decided to become “exclusive”.  The relationship quickly escalated and we became very close to each other until he decided that he was too scared to continue with the committment part… His divorce is complicated but is now nearing the finish line; his marriage was loveless and sexless, so I was hopeful that our relationship would be welcomed and not make him scared – alas, I was wrong.  Now, he tells me that he wants me in his life, thinks that I am the perfect woman for him, that he loves me, but just cannot commit to me.  I am still seeing him on a regular basis while trying to protect myself and my heart which is proving to be nearly impossible.  This is the “risk tolerance” part that EMK aludes to with the LW…

  9. 69
    Beachy Keen

    Chloe #64
    Hooray for your friend! I hope my story has such a happy ending! I am a 50+ never married woman who has had a string of bad relationships with emotionally unavailable men. By now, anytime I meet a new guy, I tend to interrogate him about any issues with potential exes or triangles. I met a great man early this year and we really clicked mutually. He told me right off that he was separated 3 years, still sharing a house because of financial reasons, but they led completely separate lives. i proceeded with extreme caution, we dated as friends, but we agreed not to be involved sexually until he was divorced. Well, when he initiated the divorce process, the W turned crazy that he was getting on with his life and had a girlfriend! He & I were both blindsided by her reaction and decided at that point to put our relationship on hold to let him deal with the process of finally ending his marriage & reaching a settlement. That was 3 months ago & I’m happy to say the negotiations are smoother. Hopefully, things will be finalized soon. Meanwhile, I hear from him daily & see him casually ocassionally. We both feel the intense pain of “love interrupted”, but reassures me that we will get back on track because we’re/I’m worth it! It’s been very hard shifting gears, but I must give him the space & support to do what’s needed. The last thing I want is to be the nagging girlfriend or “transition girl”, so I’m being very careful. And I’m forcing myself to get on with my life, and enjoy the frienship without an attachment to the outcome. Wish me luck…

  10. 70

    Divorce is super-duper painful. No one wants to feel that sort to emotional and financial trauma again. While I do think that many men want to jump in feet first, they remember that they may not be ready to be in a committed, monogamous relationship….forever….if it means they have not gotten all their post divorce playtime out of their system if they feel they need to prove themselves of feel as free as possible. 
    I have a similar situation. Divorced and not ready. Do I think that he loves me? Yes because he told me so. Does he want to be with me? Yes. He asked me to move in with him. Do I think he’s ready for the type of relationship he wants to be in with me (and vice versa)? No. Why? He told me about his current dating style and I can tell (by his words and actions) he is not over the “horror and frustration” of his marriage. I am the type of woman who is not “free as a breeze” with myself and not uptight at the same time (I.e. I don’t like the on-nite-stand type of thing).
    From what I can rationalize, he wants to be honest with me because he is curious about my opinions of him and if it didn’t matter, he would not explain himself.  We are NOT IN THE SAME PLACE. The timing is off. So as he sorts out his stuff from a divorce (emotionally and financially) and dates whomever, I have my own life and do the things I want to do and date who I choose because I am not waiting for him. It’s about living your life and not living in the false hopes and dreams of what “may” come 🙂

  11. 71

    This post. . . although kind of old . . could not have reached me at a better time! I have been mourning the loss of a relationship for several months now. And while I saw many of the warning signs, I really wanted to be wrong and trust my heart that was telling me that this man was different somehow! No matter how much he thought he was ready and over his wife (she had cheated for years and finally moved in with her lover) he was never really prepared to be single again, a single father, the sole caretaker of their home. At first, he was an amazingly attentive and caring bf, excellent communicator, but slowly I think the walls came tumbling down at once.  i saw him struggle I tried to help and offer support, but I am realizing. . .it is really his battle. I miss him so very much, and those who knew us comment that “it was bad timing” or “maybe you’ll find each other again” and as much as I want to linger in those words and hopes. . . .I know I need to move on. I have dated other men (ironically some who are seperated-augh, NOT doing that again!) but I find I compare every man to him and how he made me feel. Perhaps I need to heal more. I am not waiting for him, I just wonder if those divorcees ever seek and reconnect with their early romances? 

    1. 71.1

      I’ve rarely see that happen.  If anything, they associate the person they dated “straight out of their marriage” with the pain and confusion of those times. 
      I do have one friend who is happily married and she was the first woman the husband after his split.  HOWEVER, he had spent years without dating and had definitely “done the work” to heal BEFORE getting together with my friend.  So… possible?  Yes.  Probable?   No.

  12. 72

    I am going through this as we speak. I found this to be helpful. We are good friends have known each other for years and he even admitted that almost 20 years ago he was going to ask me on a date. The only problem is i am falling in love with him and I am holding it back as much as I can. I am not one to presure anyone and I am a divorced mother of one I have been through some of the very same things he is going through.. He is very open about everything to me about his divorce about whats been going on in court and how he feels and that is that he still loves his wife even though she has been cheating on him for years. He kept taking her back every single time but now his wife is pretty much engaged and moving on with a new man while he is left sorting out his whole life and his feelings. The only problem is I am in the middle of all of these mixed emotions. Then my emotions to top it off. The only thing I have came to the conclusion on is that I need to live my life continue to be me and in the long run either he will come around and see that I am a honest loyal loving caring woman who would never treat him as his ex wife did. Or someone else will come around and sweep me off my feet and see everything i have to offer. But…..i am a very independent woman and I don’t take alot of crap so men find me un approchable. So finding another man who even shows a little intrest almost never happens. While all along married man (the nick name i gave him) has told me that he liked me way back in the day and even though we lost touch for almost 15 years…that he wouldnt be hanging out with me if he did like me. So I just am along for the ride seeing if the road ends with him or if there are many stops along the way with maybe a detour to something that is just as good but yet better. 

    1. 72.1
      Karmic Equation

      Ina, you’re setting yourself up to be the rebound woman. As he’s going through his separation, don’t date him. Insist he date and even have a relationship with someone else first. You’ll have a better chance of having a healthy romantic relationship if you’re the next woman after the rebound, not the rebound.

  13. 73

    Wow, this thread fascinates and terrifies me, ’cause I’m living it from three different points of view:
    (1) The first man I dated after my marriage probably saved me from a lifetime of “I’ll never date again”.  He was a year and a half past an amicable split when he mustered the nerve to tell me that he was still in the midst of a big transition and not ready to be in the sort of relationship I wanted.  I didn’t see any red flags that he wasn’t ready (I thought he just wasn’t that in to me), and if I take him at his word, _he_ wasn’t aware for a while either.
    (2) I’m now dating a man whose wife left him for another man three years ago.  His relationship with his ex is comfortable if not warm, and his divorce is final.  As far as I can tell, he’s ready to move on; he thinks he’s ready to move on; he’s committing to me and stepping up to “boyfriend” behavior.  But the discussion in this thread gives me pause.  I would be his first serious relationship since the divorce, so maybe I’m the rebound.  That would suck, ’cause i’m getting really attached to him.
    (3) _My_ divorce isn’t final.  It hadn’t even occurred to me, until I read this thread, that the final gavel might return me to that un-date-able crazy I was in the first years after my marriage ended.  That would suck, ’cause my boyfriend deserves better.  Do I trust myself?  It’s been seven years and a lot of emotional work, but I know I’m not going to want to throw a party the day all the legal crap is settled.
    My two big take-aways from this thread are (1) don’t date someone freshly divorced, but God only knows how long “freshly” is; and (2) talk to your guy/ believe how he acts, but he may not really know where he stands either.  Aargh.

  14. 74

    Oh boy just read this. I got involved with someone very slowly over the past year, divorce not finalised due to financial arguing, have had some great times with him but also a lot of listening to what she did, he did etc. very intelligent funny guy . Initially I wanted just friends and some walks – we both like hiking. He seemed to develop feelings for me and in the end I initiated physical contact as he seemed so shy. Well that was about 4 months ago. We went out last sat was my birthday, he bought me flowers, earrings and supper at a lovely hotel. We had a nice day out together. On the way home before dinner he announced that he did not see himself in another relationship, not at his age, (59) and he presumed I felt the same, we had both done that and he was obviously no good at it. In the middle of my birthday dinner he suddenly blurted out that he was a complete shit waste of space. We did not go into this at the time. He left the next morning as was arranged. We had been texting daily at least. No message mon until I sent one, in fact two, I was asking if he was ok ? eventually got one saying that things were unsettled but he would be in touch. Just got an e mail today saying he could not see me for a while as has had more solicitors letters, has written off his car and other family problems and he just cant cope just now. I had already been feeling upset after the birthday announcements but had decided to just see what happened. He finished his e mail saying could I let him know a convenient time for him to phone. Well this just does not feel like an intimate supportive relationship, I felt shut out, very hurt, we were supposed to be going on holiday in march – his request . I replied very politely saying I completely understood how difficult a time he was having and how sorry I was that was the case. I said I was there if he needed me but equally ok if not. I said I was going away this weekend – which I am thank goodness. Every bone in my body every alarm bell at the beginning said don’t get involved with him he is a mess just now – I am 7 years out of divorce plus tow 18 month relationships where I was rebounding around. Even in bed he would sometimes pull away and I would say what happened and he would say he thought I was about to shout at him or push him off like his wife had. Well stupid me, I feel very sad tonight , bit tearful and guess that’s why wanting to read others experiences. He was very generous, kind, but also just retired – loss of job as well as marriage, though he was liking that – Im similar age but still enjoying work and wanting new projects and things not retirement as such, if ever. Sorry to put my stuff here, needed somewhere though. THanks

  15. 75

    This has helped bring me some clarity in my own situation, thank you for taking the time to write this.

  16. 76

    I do not understand any of this ,let him have space let him lalalla be the one over the relationship to drop you if he gets a little depressed what about us women ?yes im in this same situation my man said he loved me we spent time together and now i dont even get a are you alright nothing he could care the less is the way i see it ,its selfish and wrong ,.there is a reason men and women Divorce they were not mint to be and life is too short to wait .. wait for what ? what kills the relationship is the distrust that Men put out going for that me time, well what about us we hurt too we got int he relationship and fell in love our feelings dont matter, it doesnt matter if we are depressed or hurt so bad we cant get out of bed .but on no has he called to see if we you are alright .if two people’s heart is open then it closed with the other relationship get over it spend that time loving each other ,dont go back move forward and help each other through the hard times  get through that old relationship together dont ignore them after letting them in your life and heart it will  ,make you stronger so you know what makes you tick and what hurts the other , you isolate the one that loves you and it will fail .if you can be friends with your Ex that is good if not get away from each other and start again but do not put that person that put there heart on the line for you in the ditch because you cant get over your ex hurting you ,that is what love is is  to heal if it is from God if not then its not love at all .just my opinion sorry for the crazy writing

  17. 77
    Not Jerry

    There’s no rules.  Some can leave their old relationship, go though a divorce and it’s fine. Some can’t.  It’s all individual.

    No one-size-fits-all rule, that’s for sure.

    I was married a very long time, and my divorce was a long time coming.  So when it was finally in process I was OK in a few months.  Sure it’s hard. But it was also a relief.  I was glad of it.

    You can’t make a rule for these things.



    1. 77.1

      Excellent point, Not Jerry! One of the best ones made here, and along with Evan’s advice, a really good way to end this thread! Also helped me with perspective in my own situation. Thank you.

  18. 78

    Thanks Evan and everyone else who has commented. I have recently been in a similar situation and this has helped give me clarity on my newly separated man who was a long time friend turned more than that, but is a mess and as such pushed me away.

    If you love then let them go, if it’s meant to be it’s meant to be! Really miss my friend though.

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