Relationship Roulette: What To Expect When Dating A Divorced Man

October 18, 2012  |  
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With divorce rates what they are, the chances of you falling for a divorcee are getting higher and higher. There’s been a surge of people that married in their early twenties, when that was the trend, realized in their forties they didn’t know who their partner was, or who they even were themselves, divorced, and are now looking for a new, more informed type of love. So what are you in for when dating a divorcee? He comes with the experience, but also the pain, of a married man. Here are the pros and cons.


You can see his Ex everywhere

Even if his ex lives in another country, you can Google her, Facebook her, Twitter her, Instagram her…and unless you’re an individual of extremely strong will power, you will do all of those things. And doing those things is a form of self-torture. He loved this woman in the ultimate way once, by making the decision to conjoin lives with her. And then, he rejected her in the ultimate way, by divorcing her. You’ll obsess over anything you learn about her. Is she different from you? The same? Is that good? Is that terrible?

They (might) still have to talk

No matter how great the lawyers, there are still plenty of loose ends after a divorce. She needs the number to the handy man they used. He needs to give her dad back the golf set he lent him. The possibilities of reasons they need to get in touch are endless. And every time they have to talk, he will hurt a little more all over again. And you’ll need to console him.

He will always hurt

Loose ends aside, there will always be a place in this man that hurts over the divorce. Divorce can feel like the biggest failure to a person. Something they thought they were 110% certain about, they turned out to be wrong about. It is disconcerting, confusing and very painful. There’s a seriousness that divorcees inevitably carry. They will never be as hopeful, as positive, or as big of dreamers as the man that’s never married. They’re a little jaded, whether they like it or not.


His parents will be tougher than ever

You think his ex had a tough time winning over the parents? You’re the one that will really struggle. You don’t have to be good enough for any old guy. You have to be good enough to heal the wounds of a divorcée. You need to seem like a foolproof, 120% guarantee, sure-thing woman. They will seek out flaws in you that they didn’t seek out in the past women they dated.

His friends will be more protective than ever

His friends, even if they are sweet and welcoming to you, will have a certain undertone that says, “Be careful with him…” They will probe any story you tell them about yourself, or about you and the guy, extra carefully to make sure you really care about him. You’ll be aware of being watched always.


He may not want to marry again

Some men only want to marry once in life. If your divorcée has been divorced multiple times, the chances of him wanting to marry again are ten times slimmer. You either have to be okay with not marrying, or you have to be prepared for the long battle of winning a guy over again, that has become disenchanted with the idea of marriage.

He might not know how to date

If he was married for a long time, it’s been a while since he had to court a woman! He may take things very slowly for fear of messing up, or far too rapidly because he’s used to having a close relationship. He will be a little rusty, and a little awkward.


He knows how to commit

The guy clearly doesn’t have a problem with the idea of monogamy since he did at one point agree to be with just one woman for the rest of his life. Certainly many divorced men just want to be alone for a while after divorcing, but once a divorcee is out on the market and dating, it’s usually because he wants a close relationship again.

He knows a thing or two about relationships

He learned by the biggest trial and the biggest error what makes relationships tick. He probably knows how to communicate and compromise more than any of his never-married buddies. He knows how to incorporate somebody else into his life. He’s overcome that selfish, “everything is about me and what makes me happy and successful” phase all men go through at some point.

He knows a thing or two about himself

Nobody comes out of a divorce without doing some serious self-reflection, and perhaps some therapy. He probably isn’t afraid to look within himself, and figure out when he can do things differently and what he needs to work on. In other words, he has probably figured out what parts of the divorce were “his fault” and will pay close attention to that in future relationships.


He doesn’t have a space issue

He’s over his bachelor mentality. He won’t freak out if you leave a toothbrush at his place, or bring over some books to read while he is working. At that point, he probably won’t freak out if you just want to hang out at his place for hours upon hours, while he runs errands or works.


He knows what he wants

After the major pain of a divorce, he took some serious time to analyze all of his past relationships, and understand what he wants in a woman. So if he’s with you, he wants you. He understands what he likes about you. He’s less likely to suddenly disappear, like many guys do, when they suddenly find something they don’t like about you. He is far more perceptive from the beginning, so less surprises him.


His finances have probably shifted

He may not be broke, but if he was super loaded before the divorce and now he’s worse off with good reasons, it probably took a toll on his mentality about finances. If he did have to give up a lot in the settlement, he might be very wary to spend money on you in the beginning before he knows he can trust you.

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  • Jackie

    Dating a divorced man is only a problem if he is not over his ex, you are pathological irrational jealousy, and you don’t like kids and he is a father. Personally, the most loving partner I ever had so far was divorced with a young son at the time. Unfortunately, the problem was that he was not over his ex-wife and constantly compared us. I’m not a jealous person but I couldn’t take it after three years because it felt like she as forever a presence in our relationship because of his inability to stop being stuck on her.

    • Gracie Holford

      “his inability to stop being stuck on her (his ex)”…….that there is the number reason I will NEVER date a divorced man……

  • Everyone should have his own life, and not a person ( except for a few individuals ). So we have to find our own who wants to pass together, maybe after married, and divorced. I have to say, this is very sad, but also very normal.

    Two people together is not happy, so one can only leave. And then to find his or her lover, everyone should continue to search for his lover, must stand up, even the divorce.

  • flyer27

    damn, this is my situation right now. i swear this board is about me.

  • Christine Reynolds

    I’ve also had mixed experiences from dating divorced men. Some seem to learn from their previous marriage and recognize what they need to do to make a relationship actually work. Others learn nothing from their marriage and think the woman was all to blame for the divorce.

    • cupcake

      I cant understand why everyone is blaming the ISSUES that these men have on their divorces, Have you guys ever stopped to think that it is possibly just HIM? And, all the reasons the writer listed are the reasons that he is divorced in the first place! Why do we as women always feel the need to make excuses for these knuckleheads? It just BAFFLES me to NO END!

  • NiceGuyfinishingFirst

    As a divorced man, I can say that this list is mostly spot on, but it leaves out some things. One thing that it leaves out is that when it comes to dating someone (like me) who had a difficult end to things, what a woman really needs is foresight and patience. If you can see through the hurt and pain and recognize what type of man he was before and can be again, then with lots of love, reassurance and patience you may have a real winner on your hands. The article and slides make it seem like dating a divorcee is all work and very little joy, when the opposite can be true. Not all male divorcee’s want to party all the time, are overly selfish and need therapy. Some are, and some do, but there are those who want that close relationship.

    Also, there is this to consider: if you over 35, the chances of you meeting and dating a divorced man are probably higher than meeting someone who is single and never been married. If someone hits 35 and isn’t married you might want to wonder if there is a fear of commitment, poor dating / mating choices or if he is a guy who didn’t want to or wasn’t ready to grow up. That being said, don’t listen to others who say it’s too hard, or impossible or you would run the other way from a divorced man because you will be limiting your pool of available men and the chance of being with a potential soul mate. some of us just want to meet that right woman who will respect and appreciate when our ex-wives did not, and when we do, we want to make her as happy as we can. There is a chance that your divorcee will cause you less head aches than those who have never been married. We know the pitfalls and how to avoid then, and do… for the right woman.

    • me

      “If someone hits 35 and isn’t married you might want to wonder if there is a fear of commitment, poor dating / mating choices or if he is a guy who didn’t want to or wasn’t ready to grow up. ”

      ….or was living for God waiting for the right one

      • Smmmoke

        Exactly. He left that one out.
        For a person to wait until the time is right to do something as serious as getting married or starting a family is one of the most noble and responsible things they can do.
        I wouldn’t judge an never married ‘mature’ man or woman too harshly. It’s tough out here.
        -Says the 38 year old lifetime bachelor w/o children who still dreams of meeting ‘the one’

        • Smmmoke

          I meant to write ‘time and person is right’
          *a never married ‘mature’ man.

    • Why can’t the divorce man simply take himself off the market until he heals himself? That seems much healthier than expecting some woman to come in a nurse your hurt away. I agree with most of what you typed however.

      • NiceguyfinishingFirst

        I agree, and most men do keep themselves off until they think thay are ready/ healed…, but women need to understand that no matter when you meet a divorcee, the scars will always be there and it will take some time for him to be, for lack of a better word, better. It’s like an Athlete who is injured, all the rehab in the world won’t tell you if your ready to get back in the game. you won’t know it until you actually do.

        • I see. And I understand.

        • Gracie Holford

          “the scars will always be there”…….geez, what woman wants to deal with that lifelong baggage…….life is too short…..

    • cupcake

      I agree that divorce is not always the man’s fault. Sometimes people just grow up and grow apart. There is somebody for everybody. Just because it didnt work out with one person doesnt mean that it cant work out with another. It really all depends on the dynamics of the individual relationship, not the individual person.

  • SheBe

    Funny… As I read the comments I see these people have been with their divorcee significant other for YEARS. Right after that, they say they have been miserable with them. Why are you STILL with that person then? Is the woman’s insatiable desire to “change” a man or the hope that he would? He is divorced for a reason…. This is just my opinion expressed out of love.

    • SheBe

      *is the woman’s insatiable desire to change a man/hope he would change be to blame?* sorry. On my phone and feeding my baby….

    • Adrina

      I was thinking the same thing! 6-7 years, I mean really…you’re wasting your own time smh

    • JaneDoe

      Still with him because I LOVE him. I never wanted to change him and still don’t. We broke up a few months ago and somewhere along the line he knew he had to make changes for himself and he did. Thats what real men do when they love their significant other. I never put a gun to his head or gave him unltimatums. Can’t speak for anyone else but thats my reasoning. I would really hate to start over with someone new after all that time. And I have my reasons why

      • I think the last two sentences were the real truth. You spent so much time on and with him that you don’t want to start over.

      • Shebe

        No need to get defensive. I’m sorry Jane but “real men” don’t wait 6 years to “change” for the better for their relationship. If he LOVES you and is truly interested in investing in a real future regardless of his past, you wouldn’t have to deal with years of mess before he wakes up. I agree with Cheekee; you got in too deep. I wish you well dear and hope that his changes bring you peace and happiness.

        • JaneDoe

          I wasn’t being defensive. You asked a question and I simply gave an answer. The good with him outweighs the bad. I know who I am dealing with and so I decided to stick it out. I am no dum dum. I didn’t put all my eggs in one basket for the entire 6 yrs but at the end of the day I found that I was more compatible with him than all the other guys I dated.
          How can you say “regardless of his past”? People deal with situations differently. Yes it took 6 yrs but its 6yrs that I am not mad at. It was hard work but we got through it. I didn’t waste anytime because I know exactly who is. He is my best friend, lover, and someone who I will eventually spend forever with. So thanks for the wishes.

  • Vandellish

    So would these be ‘Bag Gentlemen’?
    From a guy with several divorced friends, frat brothers and family members (some very recently) I’d say this list is dead on especially right after a divorce. Later on, some of these men have said they’d definitely marry again (usually those who married in their 20s) and some say never no never. I think a lot of it depends on who they perceived to be at fault.
    The only one I’d argue a bit is #4. I believe a guy who’s never really had healthy and long relationships with women (sans his mother) can be EVEN MORE jaded than a divorced man. At least the divorced man has had some amount of success and found someone who they THOUGHT was the one. A man who’s never had much luck with love can harbor a bitterness that grows exponentially. These are the default playboys.

  • me

    not immediately after the divorce because chances are, I will be a rebound or he will be mad as hell

    • NiceGuyfinishingFirst

      Not all men are mad as hell… confused, yes… hurt, yes… needs time.. yes. Avoid… no, but approach cautiously. If you think he’s a good catch it’s ok to start to stake a claim because when he gets out of the fog of depression over his failure he will remember you as the person who first showed interest. Loyalty.

  • im

    I have been dating a divorced man for 7 years and I recently had to end it.My reccomendation is to not date a divoreced man. I really regret my decision now. It has caused me so much pain and the same situtions KELLS explained I have dealt with them both. But if you do date a divorced man asked him if he has sought some professional help because that may be the only way to continue a relationship with him. Black men don’t think they need help but they do.

  • leah4cali

    I have been in a relationship with a divorced man for 4 years….every single one of these slides are the ABSOLUTE truth…take the good with the bad ladies if you choose to get in this situation. While I love him with all of my heart and he is a wonderful man, but if I knew what I know now, I would have ran fast and furious…

    • JaneDoe

      Yep.. Its been 6 yrs with my divorcee and in the last yr he is just starting to act right. The last couple yrs have been a real battle. Def not something I would ever do again

    • sexylanz

      @ leah4cali Just curious, why would you have run for your life? Just starting a relationship with a divorced man so trying to do as much “research” into the matter as possible 🙂

      • leah4cali

        Every situation is different number one, but me personally knowing what I know now I would save myself the headache. There was/and still is emotional and financial damage that he has had to deal with because of divorce and of course at times those things have taken a toll on our relationship which is unfair to me because I am the party without the drama. However, it was much easier for him to commit, to compromise, to share his space and he is so much more patient that any of the men I have dated that were single w/o children. Our relationship is very slowly moving in the right direction, but if I had to do it all over again, I don’t think I would jump into a relationship with a newly divorced man.

  • Thabi

    Shooo tell me about it … Mine was à nightmare. Constantly partying and selfish as hell.

    • Ready to sign them papers

      So… Wit all the comments I just read… Would it be safe to say the same reasons you guys wish you wouldn’t have gotten involved with them at all is the same reason they may be divorced…. Imagine what their ex probably went through…

      • NiceGuyfinishingFirst

        sometimes it’s not the guys fault. The article does a poor job of acknowledging that sometimes it’s the wife’s fault.

        • This article doesn’t assign blame to anyone for the divorce. It just says these are things he may be dealing with as a result of being a divorcee.

      • Exactly . . . I would recommend anyone dating a man who has been divorced to do some recon work and find out why the marriage ended. Read through the lines of his blaming her and match that up with what you personally witness. Go into it with your eyes not your nose wide open.

        • Kells

          9 times out of 10 they are going to lie and blame the woman. Never fails. You can’t help who you like so having an open mind and paying attention is the best thing one can do.

          • You can help who you like. You control who you allow around you. Anyways. Of course he’s going to lie or minimize his role in the divorce. But if he tells you she didn’t understand that I needed my space. That would cause me to take a step back and see what he means by space. Does that mean he likes to hang out at the bars/clubs with his friends 4 nights a weeks? Does it mean he likes to be secretive or that he is just a man that likes doing what he wants when he wants without answering to anyone. That’s what I mean. Look at what he says and more importantly watch what he does.

  • Kells

    I’ve had two experiences dating a divorcee. One was bitter as hell. And the other was completely unstable. Guess he was beyond thrilled to be done with tha part of his life because he was partying every other night and flying in and out of town every chance he got. Dating a divorced man is hard work