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. 1

    Maybe there is a part of the letter that was cut before posting, but I don’t see where he says that he wants a LTR (and nothing that says he doesn’t). From what we’ve read here, what he wants long-term is an unknown.

    A lot of people don’t want that again after getting divorced, and that ambivalence might be part of his pulling back. Maybe she should ask.

  2. 2

    I think really the solution is to approach it exactly as you would any other dating situation…don’t read too much into what he says, watch what he does and how he treats you, don’t try to rush or force the situation because you are afraid, enjoy his company and wait to see how things evolve, enjoy the emotions you are having in response to his company but don’t assume there is an implied promise of forever. That’s what it’s always all about, isn’t it?

    1. 2.1
      Lawanda Gibbs

      Love this!!! Well Said!  

  3. 3

    Also, she doesn’t say anything about what she wants, either. She thinks they can have “something really special together.” What does that mean exactly?

    This goes to Honey’s point on the other thread–assuming that they both want “tradition LTR” might be wrong here.

  4. 4
    JoAnn Anglin

    Having been in an almost identical situation, I’d say proceed with caution is the least of it. His whole sense of identity will change as he gets used to the idea of being divorced, and he may never resolve his sorrow over it. For me, I was so sure of how perfect we were for each other, that I’d just bide my time. I was way more invested in this than even I realized. A 1.5 year relationship took about 5 years to get over, with individual counseling and a support group. Nobody’s a ‘bad guy,’ but it can be devastating none the less. Hold off and hold back is good advice, but as the cw song says, the heart has a mind of its own.

  5. 5

    Maybe it’s time we stopped trying so hard to be politically correct and shoot straight for once. Evan…you whimped out. Sorry, but it’s true. The gentleman should back off and so should she. Any divorce class in the world that is worth it’s salt will tell you that right after a divorce, or worse yet, before it is final, is NOT the time to be out forging new relationships. Most classes tell you it’ll be a good year, or more realistically two years, before you are healed, healthy, and ready top start dating again. It takes two healthy people to have a healthy relationship, and if a part of you is still in the old one, then that’s just all that much less you have to give to someone else…and we all expect to have 100% of someones heart when we’re giving 100% of ours. It simply isn’t fair to the other person not to have 100% to give. If you are going through, or just getting out of a divorce, you are hurt, you’ve suffered a loss and there isn’t any getting around it. Thing is, we think we are ready when we’re clearly not in most instances. I know this from experience. It’s easier being on the outside looking in than being the one who is all excited about someone and looking for ways to justify it, I understand that. But the truth is the vast majority of people are not ready right after a divorce…especially if the marriage lasted 34 years! Now, I’m not saying it can’t work for these two, but she has to give him some time, and he has clearly stated he doesn’t know where he’s at.

    1. 5.1

      Well said Paul.

    2. 5.2

      So on point. I am in this situation currently and I have decided to back away to protect my heart as well as my friend who’s going through a divorce currently. We are very much smitten by each other. However, we both need to be healthy for this union to be successful.

  6. 6

    I whole-heartedly agree with Honey (#2). It’s all a gamble anyway, whether you’re recently divorced, been widowed for years, never been married, or have been divorced 14 different times. Everyone heals differently and everyone has their own relationship history, clear back to their family of origin. In spite of that, I still think Evan’s advice is sound and comforting. I know many women (me included) tend to think the bold, definitive, even courageous move was to get out of Dodge the minute the guy shows any kind of hesitation..what I call The Ambivalence Reactionary Maneuver. Cut your losses, don’t give him a chance to dump you, march out of it with your head up high, and be sure to slam the door on your way out. Yea, yea, yea. You go girl. Well, that clean-break high lasts about… a day. Real maturity, self-love, and courage are what’s at work when you can hang in there — not like some needy, clinging puppy and not like some delusional overly-optomistic Pollyanna, but as a realist. If you keep yourself open to the man while at the same time keeping yourself open to the rest of your life, too — which you should do anyways, whether in or out of a relationship — you’ve got the best shot at having a relationship that will endure these rough spots and continue to grow into something deeper. No guarantees here, but there never is. I think Paul (#5) has some very valid points, but I disagree with the conclusion that You Should Never Date A Recent Divorcee. I was separated a year after a 20 yr marriage when a man initiated a relationship with me. I was clueless at the time, thought I was doing “fine,” but was actually a basketcase — a complete novice at being a single adult again. This guy stuck with me, was empathetic and self-confident but so very, very kind. Without being a doormat, he continued to treat me lovingly but gave me whatever space I wanted (trust me, I didn’t know what I wanted). I flip-flopped over and over and when my divorce became legally final, all of my insecurities erupted all over again. Eventually, due to his patience and steadiness, I was able to see this new man as an incredible gift and started showing my sincere gratitude, got outside of my self-involvement and gave back all that had been given to me. I was extremely lucky, I know, and I’m not saying everyone should be that patient. My point is simply that there are no hard and fast rules; and even if there were, there are exceptions to every rule.

    For this one, my vote it so hang in there, with poise.

    1. 6.1

      Thank you for this.   I am divorced and have a child.   I am with a guy who says he loves me (I love him too and I know I am a strong person so whatever is thrown at me I can handle).   However, we are Asian and therefore parents play a big part in relationships.   He is spending many hours thinking about how this will hurt his parents and therefore is confused about balancing his own happiness with his parents and with that hurting me too.   I keep thinking what you have written “I’m going to get out before I get dumped etc and have tried to get away but we love each other and he doesn’t want me to let go.   So it was nice to at least read that many of us women feel like running before we get hurt again.   I think if he can sort his own issues out then we can work well…he is very communicative and wants to understand me and vice versa.   Something I’ve never had before.   

  7. 7

    I think you have done a great job describing some real thoughts that are going through many men’s head in a time like this. Everything isn’t black and white and some people can’t handle hearing that and some people can.

  8. 8

    Back off. You are not his therapist, but hopefully a future girlfriend or wife. Be thankful that he is a good communicator, but you need not carry his load of doubts, and wear yourself out in the process. Your guy needs urgent therapy, not an overly patient almost-girlfriend. Then, AFTER he’s healed, he may be a great guy for you.

  9. 9

    I’ve got to agree with Paul. I have been there. Twice. Both men had been married less than 10 years, and I can tell you, they were NOT ready prior to the divorce. They WANTED to be ready, and yes, they liked me a lot and thought they WERE ready, but when push came to shove, they bailed. When the LW says “I think it just really hit him, thought he was doing fine.”, boy, does that sound familiar.
    In one case, the guy was a already good friend, and our friendship was ultimately ruined. In the other case, once the divorce became final, the man was much more upset about it then he thought he’d be. Both men had assured me they were fine with their break-ups. It’s very hard for me to imagine a man being ready so soon, after 34 years.

    Sure, every situation is different and should be evaluated on its own merit, but the odds on this one aren’t very good. That doesn’t that mean they can’t work down the road, but I’ve found that getting involved too soon can ruin any chance of things working out in the future. I’d back off on this one – I don’t believe this man, even with the best intentions, is emotionally available. The LW doesn’t want to end up being the rebound girl, and her man saying “he’s not sorted through his emotions like he thought he had” is the equivalent of waiving a big, red flag.

    Janet #3
    “Something really special”. Yes, she means an LTR, not a short-term fling. She wouldn’t bother writing this letter if she didn’t.

  10. 10

    I have been there. Twice. And I’ve had friends who have been there as well. In my case, both men thought they were ready, wanted to be ready, said they liked me a lot. But they weren’t ready. Both men had been married less than 10 years. When the LW says “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”, it sounds painfully familiar. In my case, one man was a good friend (friendship ruined after the romance failed), and the other fell apart as soon as the divorce became final. I’m told that, no matter how long people are separated for, the finalization of the divorce is still very traumatic.

    Yes, every situation should be evaluated on its own merit, but I don’t believe that it’s possible for this man to be ready for a new relationship so soon, not after ending a 34 year marriage. Perhaps this relationship can work out later on, but the odds on it now are not good. This man simply isn’t emotionally available. He told me last night that he came to the realization that he’s not sorted through his emotions like he thought he had” is the equivalent of her man waiving a big, red flag. She doesn’t want to become the rebound girl, and she is better off waiting until her man has had a chance to mourn the loss of his marriage. And yes, I’d guess that the LW is hoping for an LTR with him.

    Zann #6
    While I’m glad your guy stuck with you, I can’t say that flip-flopping “over and over and over again” is really a great deal for the other person.

  11. 11

    She already answered it – he hasn’t sorted through his emotions. He’s in no shape to enter a new relationship. I’m divorced, and I started dating immediately after separating. I needed the touch of a woman. 9 months later, I met a woman I wanted to be in an LTR with. We broke up a year later. It wasn’t until 3 years after my divorce that I had truly processed most of my emotional junk. And during those 3 years, I tried reconciling with my wife on multiple occasions. I was in no shape to move on.
    If a divorced person is still working through stuff, they aren’t ready for a lasting relationship. Period.

  12. 12

    I was in a similar situation about six months ago, although this man’s divorce was not almost final. In fact, it was not going well at all. There’s a lot of anger between him and his estranged wife, the divorce is contested on a number of issues, there are children involved, etc. Any lawyer worth having will tell you not to date while your divorcing not only because of the emotional issues, but also because it makes things worse from a legal/settlement standpoint, particularly in a contested divorce.

    But, I digress. In the end, he broke it off. We had a conversation after that, where he mentioned staying in contact. So, I sent him a few emails, and never received a response (never mentioning getting back together, but saying that if he wanted to talk, I was there to listen). I realized that he either didn’t want any contact with me or contact by me made him feel pressured…or as is more likely the case, probably a combination of the above and a lot of other things I have no idea about.
    I realize that we didn’t go out that long, and he doesn’t owe me anything. He may have owed it to both of us to know the truth of where he was at, that he wasn’t really ready to date seriously and as that was the case, he shouldn’t have let things go as far as they did (as I shouldn’ t have either). However, I respect the fact that he talked to me about it and was as honest as he could be instead of just disappearing.
    Just so you know Evan, I want the truth from men, and sometimes it hurts…a lot. I don’t always know what to do with the hurt, not because I don’t want to hear it, but because often men send mixed messages trying to avoid hurting womens’ feelings (actually most people do this…men and women alike). When in this situation, a man often flip-flops and says things you have no idea what to do with because he contradicts what he just said making it hard to know what the right thing for you to do is.
    Sure Sunshine can ask if he wants a LTR, but one minute he’ll say yes; the next he’ll say no. He’s on an emotional roller coaster and will likely flip flop several times. So what does she do? Should she really ask that question?
    I get I should have been more cautious, paid attention to the red flags, not had sex with him and all of that. I should have slowed things down and taken more time to get to know him and see where he was at. But, I didn’t and I screwed up. I know he bears some responsibility also, but given what he’s going through and I saw the red flags, I believe I bear the greater responsibility to have been the one to slow things down.
    Having said all that, knowing what I should have done differently from the start, I have a few questions: When you say back off and give him space…what does that mean? To be supportive…what does that mean? Should I have done something differently, i.e., not just stopped contacting him when I didn’t receive a response to a few attempts to stay in touch?
    I ask these questions because most of the men I will date in my age group will likely be divorced or in the process of getting a divorce, so I’d like to know if there are other things , other than those I’ve already mentioned above, that I could and should do differently.

    1. 12.1

      Oh Casey,
      I understand your feelings and thoughts….Was in the situation like you, and now on my way to recover and move on. It’s really hard process.

  13. 13

    What’s the rush? Why don’t you continue to spend time together and see if it develops into “something really special”?

    It either will…or it won’t. No crystal ball prediction.

  14. 14

    A lot of good discussion here. OP seems to be approaching things in the right way, asking good questions. Bottom line is that actions speak louder than words.

    Guys who’ve been divorced have told me never to date a guy who’s going through or has just gone through a divorce if you’re looking for a ltr. They may end up having true feelings for you but at the end of the day only needed compantionship/diversion/ sex to get them through an emotinoal transition and aren’t able to commit emotionally.

    Of course there are always exceptions but proceed w caution. OP, you’re right to be skeptical. You’ve been friends w this guy for a while and sounds as if there’s a great deal of mutual respect. And he’s already told you he needs to sort things out. Allow him the space to do that, spare yourself further heartbreak. if it’s meant to be he’ll return when he’s ready.

    I have too many girlfriends who’ve had their hearts battered by seemingly terrific guys they’ve dated while ‘in transition’.

  15. 15

    Casey #12

    I have learned that you cannot go by what a man says, you have to evaluate him on your own reading of the situation. So if you are getting mixed messages, that is a red flag. But don’t beat yourself up. You really liked him and hoped for more, and you hoped the positive messages would win out over the negative ones.

    I never date separated men now. It just seems so unlikely that they’ll be ready for what I want. But if I was interested in someone going through this, I would tell them to check back AFTER the divorce is finalized, and maybe WELL after.

    I have been surprised (as have my friends) to encounter men who aren’t ready for a relationship – or even dating – for YEARS after their divorce. I’m talking 5-10+ years. I suspect they should have gotten professional help, but didn’t. In general, I also think that men process things differently. Women will get therapy, will rant and cry to their friends, while men often behave more stoically, and have a more difficult time expressing emotions.

  16. 16

    Ava @9: “something special” means “LTR” to YOU. We don’t know what it means to the letter writer. It’s a good question to ask her.

    Another good question to ask: What do the phrases “LTR” and “something special” mean to you?

  17. 17

    I agree with many of the sentiments here. I know from my own excruciating divorce experience after a 26 year marriage, and from what I could gleam from my former husband’s experience, no matter how ready you believe yourself to be in moving on, the reality of going through the divorce process and solidifying this painful, final act in what was once a loving and lasting relationship is difficult to go through, and fraught with emotional peril.

    He will have his good days and his bad days. As I am certain you know, he is likely dealing with feelings of guilt, regret, grief, anger, and confusion, and now he’s also dealing with longingly held feelings for you, Sunshine, that have now been escalated and compounded through your intimacy.

    My suggestion is that I would let him know that while you care for him and you respect how he feels about you, and that you hope to have a future with him, you feel that it does your relationship a disservice not to be there wholly for each other. If your relationship is truly meant to be, then when his divorce is through, and he has allowed himself to have that emotional space and time that he needs to fully heal and find himself again, then you will be together, if that is what you both still want at that time.

    Otherwise, you will become a part of his painful journey, and in the clearing, his new awakening and possibly yours, too, may reveal a different light that may have you realizing that his burden was not worth carrying.

    This takes clarity and strength, and love of a different kind. I wish you well.

  18. 18

    Janet #14

    LTR and “something really special”, yes, for me they’d mean the same thing. I can’t read Sunshine’s mind, but if she is in fact, “falling in love” with this guy and writing a dating coach about her fears, my guess is that’s where she would like it to lead. That’s what I think “hopefully he can work through this and move on, hopefully with me” means.

  19. 19

    Ava @ 18: “Falling in Love” is from the headline of the piece (an editorial insertion) and not from the letter itself. Again, maybe she says that in some part of the letter that didn’t make it onto the site, but it isn’t in the letter as posted.

    I still don’t see where the LTR part comes into this, and today I am feeling the frustration of other posters on here who have spoken about this–that “dating” isn’t the same thing as a relationship, or an LTR, or a marriage. Further, not all people who are dating are looking for LTRs (especially among the male population), not all LTRs are marriages, not all marriages are LTRs. I mean, don’t you all know people with relationships that fall into these different categories or am I the only one? (Or maybe those with other viewpoints have left this board!:) )

    But I do encourage this kind of discussion–every discussion starts with an agreement on the definition of terms. And it’s good to know, Ava, that you yourself hold the expectation that dating leads to falling in love to an LTR/marriage. It is also good to realize that not everyone holds this same expectation so that you can have these kinds of discussions upfront and not assume that the person you are dating wants or is expecting the same relationship trajectory. A lot of women get hurt when they assume this about the men they are dating. And, to be honest, I know many men who have been hurt in the same way.

  20. 20

    Evan’s got great advice no doubt about it. We also would encourage you to post the question on our site http://www.Leftos.com. We have a very dedicated, active, mature, and loyal user base that hopefully could help you. It’s also a very interesting conversation. The notion that Evan brings up about women not wanting truly hear what men are thinking is another great discussion. We’ll definitely point our users this way to check out this post.

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