Challenges Of Dating A Separated Man Going Through A Divorce

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dating a separated man

Disclaimer: We have nothing against dating a separated man nor do we think that a separated man who is going through a divorce should be off limits. Yet we can’t (neither should you) turn a blind eye to the challenges that come along with such a relationship. As long as the divorce is not final, he is still legally another woman’s husband. I hope you comprehend the gravity of that fact. 

As they say, the heart wants what it wants. If you think you are falling in love with a separated man and you are willing to take a leap of faith and build a relationship with him, we can at least offer you a reality check. Do you consider yourself strong enough to deal with all the emotional, financial, legal, and social hurdles you’ll encounter along the way? 

If so, we’re here to guide you on the journey of dating a separated man with a lowdown on the potential challenges you need to brace for, in consultation with emotional wellness and mindfulness coach Pooja Priyamvada (certified in Psychological and Mental Health First Aid from Johns Hopkins Bloomberg School of Public Health and the University of Sydney), who specializes in counseling for extramarital affairs, breakups, separation, grief and loss, to name a few.

Challenges Of Dating A Separated Man

One of the major disadvantages of dating a separated man is the uncertainty of your place in his life. Does he simply need an emotional support system to go through this difficult phase or is he looking for something more meaningful? It may sound a little too harsh, but maybe to him, it’s nothing but a passing fling to keep himself distracted from the complications in his personal life. The odds of that are high if you are dating a separated man who lives with his wife. 

Not knowing how much he wants you involved in his life as he navigates the turbulence of a divorce can make you feel extremely anxious. But that’s not all there is to dating separated man problems. In case he wins the child/ren’s custody, are you willing to take on their responsibility as well? Or worse, what if he wants to give the marriage another chance? Although statistics show a lower percentage (13%) of reconciliation after separation, it’s still a risk factor. 

Infographic on - challenges of dating a separated man
Challenges you can expect to face while dating a separated man

You see, there is a lot to consider before you even consider taking your relationship to the next level. Pooja says, “The key challenge is to develop empathy for this man who has probably loved another woman as deeply and as intensely as he loves you, maybe even more. Will your ego be magnanimous enough to hold space for this? 

“Also he might have had a complex relationship with this estranged spouse – they could have kids together, they could have been business partners/colleagues. Can you handle their space in his life maturely and with grace? You have to be prepared for putting in greater emotional effort when dating a separated man.”

We are not saying it has to be this complicated for every couple. Proper communication can save you many a sleepless night wondering where this relationship is going. But for yours to be one of the dating a separated man success stories, he would have to wrap up the legal obligations to be with you. We have listed out 9 typical challenges of dating a separated man that you should watch out for before you fall head over heels for him:

1. Is this the real deal or just a rebound?

If you are falling in love with a separated man who’s recently split from his wife, he will be at his most vulnerable in this phase. There is a clear lack of affection and mutual understanding in his marriage. The moment you enter his life, lending him an ear to vent and validating his feelings, he may hold onto you like a drowning person grasping at straws. Being with you could very well be an impulsive decision given that he is in the middle of an emotional crisis right now.

Pooja categorizes rebound relationships into 5 stages: pre-rebound, honeymoon, conflicts and reality, nostalgia and comparison, and the epiphany. And non-rebound relationships go through three: lust, attraction/obsessive love, and attachment.  

She says, “These signs make it easier to understand what kind of partnership you can expect while dating a separated man going through a divorce. If it seems like a rebound relationship to you, ask him to take it slow and give him the space and time to recover from the previous relationship.”

Related Reading: Effects Of Divorce: Psychological, Emotional And After Effects

2. Commitment may not be a word in his dictionary now

One of the major red flags when dating a separated man is that he would be skeptical about committing to you. To be honest, we really can’t blame him for acting like a commitment-phobe when he is coming out of such a massive relationship failure. Of course, it’s not a point of discussion until the divorce is final. But if you see him deliberately stalling the paperwork, probably he still feels attached to his ex-wife.

When you ask him to define the relationship, he would be in two minds about whether it is cheating on his ex or not. A Reddit user shares, “Waiting around on a person to file for divorce is hell. It’s really difficult to grow your relationship as he’s legally married to another person. You should say that you need a break until they file. I think it would expedite the process. Right now there’s no incentive for him to push things along because he still has you.”

3. Dating a separated man comes with an emotional baggage

Studies show that the recovery timeline for a divorce is approximately 18 months. So, if you are dating a separated man going through a divorce, chances are he is not entirely invested in the relationship. A divorce procedure can cause havoc on the mental health of a person. 

He may be too drained, both psychologically and emotionally, to start another relationship from scratch. Plus, a shadow of his mental turmoil would also fall on you. He might use you as a punching bag to release the pain, the frustration, the anger. We know you signed up for a loving, romantic bond. In reality, you may end up being this guy’s unofficial therapist. 

Pooja says, “If you are both serious here and see a future for your relationship, then you need to give him time to process his failed marriage. This might need lots of emotional support from you as a partner and sometimes also professional loss and breakup counseling. If his emotional baggage is affecting you too, then you might also require help and guidance.”

4. The prolonged legal procedures will keep him busy

When you talk about dating separated man problems, this is a big one. Vivian, a television journalist in her 30s, shares her experience with us. When she started dating Mark, he gave her the impression that he can’t wait another day to cut all ties with his past and move in with her. Vivian thought she would make another headline on those ‘dating a separated man’ success stories and prove everyone who told her not to get involved in something so twisted wrong.

Related Reading: 11 Ways To Remain Sane During a Divorce

“Little did I know the divorce proceeding will hog most of his time and energy. We hardly had the opportunity to spend some carefree quality time alone. Even when we were together, every conversation somehow turned into a discussion about the divorce. I saw us slowly drifting apart. By the time it was all over, there was very little romance left between us,” she says. 

You know how ugly the alimony fight can become. Seeking custody of a child is another struggle in itself. Overall, the legal battle can get dragged on for a long, long time. Quite naturally, he will be distracted by these complications. Dating a separated man could test your patience in every possible way. You need to be prepared for that mentally. 

5. Financial crunches will be an issue

Listen to the story of one of our readers from Florida, “I was aware of the disadvantages of dating a separated man. I guess I never really comprehended how they could affect my personal life until the financial issues started cropping up. I am not someone who expects their man to spend a fortune on gifts or to arrange fancy dates every weekend. 

“But given that I was not born with a silver spoon and work really hard to make a living, I believe in sharing expenses. I knew the lawyer’s fees, selling assets for the alimony – it was all placing overwhelming financial stress on him. As it was on me as well. I had to bear a large portion of our expenses because he could rarely pitch in.”

Pooja adds, “Financial security is crucial in life, and if he is going through a crunch, it can become one of the major dating separated man problems. If his divorce is going to affect your current financial situation adversely, it is a good idea to talk clearly about it. 

“Plan your money well, maybe curtail extra expenditures and support him as much as you can. Of course, lack of money can often become the main grouse in a relationship too. So, try to avoid falling into that pit and try to stay afloat amidst the crunch.”

6. Could you take things any slower?

Are you surprised? Honestly, we are not. The relationship is bound to move at a ridiculously slow pace when you are dating a separated man. This person’s marriage just ended. He is a walking talking storehouse of anxiety, insecurities, trust issues, and more. If you pester him to spend the holidays with your family or try to discuss how many children you want to have, it might backfire.

Especially if you are dating a separated man who lives with his wife, he would try to keep it on the down low. As long as the divorce isn’t final, such personal matters can be used against him in court. He would definitely not want to give her any more ammunition than she already has. 

Related Reading: Fear Of Relationships After Divorce. Face These 10 Fears First

7. The kids will top his priority list

In an ideal world, we fall in love with a single, independent, emotionally stable person and live happily ever after. But real life is far from that utopian dream. Here you may feel strongly for a guy who’s going through a divorce and find the disadvantages of dating a separated man staring you right in your face. 

Say, you are having the best time with your man, sitting at a romantic cafe, sipping on hot chocolate. Just about then, the phone rings and he leaves to help his kid/s with their homework. Sometimes, you will be shocked to see yourself competing with his child/ren for his attention. But all in vain, cause no matter what, you will be his second priority. 

If his child/ren are young adults, they will have a say in your relationship. In fact, there could be a constant comparison going on between you and their mother. Even when it comes to younger children, you will have to put solid effort to create a place in their hearts. Either way, they could be welcoming or spill hatred against you. Keeping this in mind, measure your steps wisely from this point forward. 

8. Having the ex-wife in the picture can be irksome 

Dating a separated man who lives with his wife has this added pressure of dealing with an ex. Are you ready to handle the repercussions of his hot and cold relationship with his ex-wife? Even if they are staying apart, this woman can keep a tab on you. She might even see you as a potential threat or a reason behind her marriage being a shambles.

In a completely different scenario, if your guy is separated for a long time, the hostility between them may have mellowed down by now. Perhaps, they share a friendly bond and co-parent the kids. Seeing them so close, managing everything together, jealousy might rear its ugly head. Falling in love with a separated man is a tough ride as it is and the ex-partner certainly makes it harder for you to not drown in a pool of relationship insecurity. 

According to Pooja, “Maintaining any relationship is a two-way process. You can only do your 50%. Never speak ill of her to him or anywhere. Respect their years together. If they have kids, respect their co-parenting space. He could miss her on their special days, that’s natural. Do not hold it against him or her.”

Related Reading: Finding Love After Divorce – 9 Things To Be Mindful Of

9. He might change his mind about the divorce

You may not like the sound of it but let’s break it to you before he breaks your heart. Being with you during the separation period could work like an eye-opener for him. Eventually, he may realize that what he had with his wife was pretty amazing and he is not ready to give that up. It’s certainly one of the red flags when dating a separated man. 

dating a separated man who lives with his wife
He may want to go back and fix his broken family

Suppose the thought of leaving you never even crosses his mind. Still, you can’t help but worry about the what-ifs. The question is: for how long can you put up with such terrible relationship insecurities? Because dating a separated man going through a divorce may put you through the same. 

Puja says, “Any relationship can end anytime. Yes, when you are dating a separated man there is a possibility of him wanting to go back. You need to discuss this openly with him. Is there a space for reconciliation? Your preparation for such an exigency shall depend on his response. A relationship must never be codependent. You both must be together because you want to. Always be prepared for impermanence though.”

Key Pointers

  • You could be just a rebound for him
  • Dating a separated man comes with emotional baggage
  • He would want to take things slow and be shaky about commitment
  • There might be a constant financial crisis
  • His relationship with his kids and ex-wife might be an issue
  • He may want to go back to his wife after the separation period

There you go. The challenges of dating a separated man are laid on the table. Now it’s all up to you to assess their severity and make a wise decision. If you ask us, we won’t advise you to get too emotionally attached and dream of a happy future with this guy. At least, until you hear the final verdict. 

If it’s only a fling for you as well, then there is hardly any cause for concern. But it is still better to communicate expectations from the very beginning so that you’re both on the same page. We wish you all the strength and courage to face the obstacles and make it to the end. 


1. Is it OK to date someone who is separated but not divorced?

There is nothing wrong with dating someone who is separated and going through a divorce. But don’t get your hopes high just yet. Try to figure out their true intentions and whether this is only a rebound relationship for them. Wait until the legalities are complete before you start planning a new life together.

2. Why shouldn’t you date a separated man?

Don’t put all your eggs in one basket if you are not ready to meet the challenges that come along with dating a separated man. It will put you through an awful lot of mental turmoil – insecurity, jealousy, misunderstanding, all of it. Plus, a part of his financial burden might fall on you. Think of all the adversities before you let yourself fall hopelessly for this man. 

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