10 Questions to Ask Before Dating a Separated Man

dating a separated man
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Did you know that nearly half of all marriages end in divorce? I have a front-row seat to the evolution of a separated man when it comes to moving on and being ready for love again. I have been a practicing divorce attorney for over ten years. In my practice, I see men at all stages of separation, from the initial split to the final divorce decree.

If you are on the dating scene, you will likely encounter potential suitors that are either divorced or separated from their spouses. Perhaps you are already involved with a separated man not sure if the relationship is right for you. Everyone deserves a second (or third, or fourth) chance at love and happiness. However, you cannot go into these relationships without recognizing that dating someone who is separated or divorced is different than dating someone who has never been married.

I don’t just offer this advice as a divorce lawyer. I also have single friends who were involved with separated and divorced men. So, armed with this knowledge, I will give you ten questions you need to get answered before you start dating a separated man.

1. Where is he in the divorce process?

Before I discuss the emotional aspects of dating a separated man, I wanted to clarify the difference between someone who is divorced and someone who is separated. While this is a legal distinction, it can also affect whether pursuing this relationship is emotionally right for you.

When someone is separated, they are not legally divorced. Therefore, they are still technically married to their spouse. First, let’s discuss the legal effects of this. When someone is separated, they are not able to marry someone else until they are officially divorced. Doing so would be bigamy and is illegal.

If you are dating a separated man, you should find out where he is in the divorce process. How much longer it is going to be until he is officially divorced? It is particularly important if you are looking to get married. If a divorce action hasn’t been filed, it may take years until he is officially divorced. Do you think you are ready to wait?

If you are dating a separated man, you should find out where he is in the divorce process. How much longer it is going to be until he is officially divorced? Click To Tweet

Second, the stage of his divorce process may be a signal as to whether he is serious about getting divorced and if he is ready for a new relationship. Has anything been filed in court? Have he and his spouse discussed the division of assets or child custody? Are they still living together? The answers to these questions may signal that he doesn’t want to get divorced, and this separation is not severe or permanent. Remember, many couples separate, go to counseling, and get back together. Some even repeat this cycle multiple times before calling it quits. Therefore, you need to ask yourself: is this separation leading to a divorce, or is it just a bump in the road of his marriage? If it is the latter, you should move on. Getting caught in the drama between him and his spouse is not anywhere you want to be.

For some, dating a man who is technically still married may be against their religious beliefs or moral values. As an attorney, I know how long it can take to resolve a divorce case in the court system. Therefore, the fact that the divorce is not yet final is not enough for me to pass on dating a separated man. Instead, I would look at whether he is taking active steps to end his marriage as a signal as to whether the relationship has any long-term potential.

2. Does he have children?

Children add an extra layer of consideration when deciding if dating a separated man is right for you. First, what are your thoughts on children in general? Are you a place in your life where you want the responsibility of being a step-parent? Or, on a less serious note, are you okay with having your weekends revolve around soccer games and his custody schedule? If the answer is no, then you should probably not be dating someone who has children. There is nothing wrong with that. Don’t feel guilty. It doesn’t make you Cruella Deville. You have every right to have the relationship you want, and it is okay if that doesn’t involve children at this stage in your life.

Even if you like kids and want to be a parent yourself someday, you must understand that your partner having children from his previous marriage is going to affect your relationship. His children are going to be his priority, not you. You may not be able to see him when you want because it is his custody weekend. You must also be okay with plans changing at the last minute because a child is sick or has a school recital.

Also, you need to remember that with children comes the children’s mother. What is his relationship with her? If there are constant fights and court proceedings, you need to ask yourself if you want to bring this baggage into your personal life. I do not date men with children. I get enough custody drama during the work hours, and my concern is that I will have to take off my girlfriend hat and put on my lawyer hat during my time. I don’t want to do that.

However, I don’t want you to make my decision as an edict that men with children are not dateable. They certainly are! For example, maybe he and his ex have an excellent relationship and are great co-parents. If so, go for it! You need to assess the actual situation and decide whether it is the right fit for you and your needs.

3. How many times has he been married?

According to a Pew Research study on remarriage, men are more likely to get remarried after a divorce than women. Most of the men that you will meet will likely have only been married once, mainly if you are on the dating scene in your 20s, 30s, or 40s. However, there are some guys out there who divorced multiple times. Before getting involved in a relationship with a separated man who is on his second divorce, you need to find out what happened in his previous marriages and why they didn’t work out.

You know the adage; a leopard doesn’t change his spots? Well, it applies in this case. If both of guy’s previous marriages ended because of his cheating, chances are, he will do the same to you. He’s the leopard, see his spots.

If both of guy's previous marriages ended because of his cheating, chances are, he will do the same to you. He's the leopard, see his spots. Click To Tweet

Conversely, maybe his first marriage was a youthful misstep and the second, while longer, didn’t work out because of circumstances. In this case, I would undoubtedly consider dating this person. I’ve had many clients who match this example. They are wonderful men who are looking for love for the right reasons and can have a successful relationship. We all make mistakes, and I give them credit for trying to get back out there and get it right.

4. Who decided to end the marriage?

Marriages end for various reasons and in all types of ways. Some end with a fiery argument and someone screaming, “I want a divorce” while they hurl a book at the wall. Others quietly fizzle out to the point where the parties are merely roommates and no longer lovers or even friends. Still, for others, they are blindsided by their spouse’s decision to end their union.

How did this man’s marriage end? You may be surprised, but the fiery argument is not the biggest red flag for me. Yes, anything involving rage and violence should be concerning, but ending a marriage is tough stuff. I would forgive anyone that has a moment of anger at such a time if it is not indicative of his general behavior or demeanor.

Instead, I would be more concerned if his marriage ended without warning. If it was him who initiated the split, does it indicate his failure to communicate in general? Communication is key to any relationship. If he has a hard time expressing his feelings, particularly those of unhappiness and lack of fulfillment, how is that going to be different in your relationship? I don’t see the pattern changing unless he has sought professional help.

If his spouse ended the relationship, then what are his feelings about the way that it ended? Is he still in shock? Is he angry? Men in those stages are not ready for a new relationship. They haven’t had enough time to process what just happened to them.

It doesn’t mean that he will never be ready or won’t be a good partner in the future. He isn’t in a place to have a meaningful relationship right now. If this applies to you, there is no harm in staying friends with this man. However, don’t sideline yourself from the dating game because you are waiting for him to be ready. Processing a divorce takes time, and it is different for everybody. I have clients that take months, and others take years. Keep your options open, and if you are still single when he is ready, go for it!

5. Why is he getting divorced?

The way marriages end vary and the reasons they end may vary as well. Some couples grow apart and are no longer compatible. Other unions end because of a defining event such as drug use, abuse, or adultery. Based on what I see in my practice, most marriages end for lack of personal responsibility as to how one’s actions affected their spouse and thus the relationship. The demise of a marriage is usually not one-sided. Both parties have a role to play in the failure of their union.

Regardless of the reason why the marriage ended, it may affect your relationship with this separated man. Therefore, you should know what happened, at least in general terms. However, make sure that you tread lightly when broaching this topic. In my experience, some men will bring it up themselves while others may deflect.

Most marriages end for lack of personal responsibility as to how one’s actions affected their spouse and thus the relationship. Click To Tweet

If the man was the party at fault, he might not want to tell you what happened for fear that you will judge him and end the relationship. This man may also not want to appear as the victim as he thinks it will make him look like less of a man in your eyes. Still, others are more than happy to discuss the end of the marriage. It is particularly true if he does not think he shares any responsibility in the breakup. Be wary of this man. Remember no one is blameless at the end of a relationship. A lack of self-awareness in the separation is a red flag that this may happen in your relationship as well.

Fixating on the reasons of his breakup and bringing it up over and over will probably open old wounds for him and is a turn-off. While you should know why the separation occurred, be sensitive that he probably doesn’t want to discuss it every time you go on a date. Would you want to talk about the worst things that happen to you every day? Probably not. I would suggest having a long discussion about it and then put it to rest.

6. What is his financial situation?

Relationships should not be about money. However, finances are a fact of life and dictate our everyday choices. Therefore, you should consider the status of your partner’s finances when deciding to begin a long-term relationship with him.

There are some unique financial issues when it comes to dating a separated man. First, if he has children, he is likely paying child support. How much is he paying? Can he afford it? If you were to marry, his child support expenses might affect your lifestyle. It is true not only for a basic child support obligation. There are other expenses for children to consider, such as tuition, childcare, and after-school activities. Are you okay with having these expenses affect your life and your financial goals?

Second, if this separated man is not yet divorced, he may be in financial limbo. Likely, he and his former spouse haven’t decided how to divide their assets. He may also need to pay his wife alimony. Financial insecurity is difficult for people, particularly men. The uncertainty related to his life and financial situation after the divorce is over may affect his ability to commit to a long term relationship.

Third, many times, separated people find their finances in dire straits during and after a divorce. It happens because they had to pay lawyer fees, spousal support, and other related expenses. It can result in this man incurring tremendous debt. Having debt will affect his ability to plan. Are you looking to buy a house or save for your retirement? If this man can’t contribute to those goals because of divorce debt, how does it impair your ability to reach those milestones?

7. Do you both have the same relationship vision?

Not everyone wants a house with a picket fence and two kids. Sure, many people want to be married. Some people want a committed relationship, and marriage is not a priority for them. Still, others only want to date around and have fun. All of this is okay if you and your potential partner are on the same page.

While this advice certainly applies to all relationships, it is particularly important when dating a separated man. If he is newly separated, likely, his emotions are all over the place. He doesn’t know what he wants because he is going through one of the most significant transitions in his life. Therefore, it is essential that he thinks about what kind of relationship he wants in the future and articulates that to a potential partner.

If you know what you want and this man cannot tell you what he wants, it doesn’t mean that you aren’t compatible personality-wise. It means that you aren’t compatible relationship-wise. You both need to have a successful relationship, but possibly someone else.

8. Is he emotionally available?

Okay, so you know that you need to figure out what kind of relationship this separated man wants. However, what he says is not as important as how he behaves. It is not enough for him to say he wants a relationship with you. He must be able to show it.

One of the most important ways for him to do that is to be emotionally available to you. It means that his heart and his mind need to be open and ready to trust a partner and find love again. Divorce and separation are scarring. They make people want to put a wall around their heart and never show vulnerability ever again. Is his wall still up? If so, then no matter what you do, how awesome of a partner you are, the relationship will not work out.

It is not enough for him to say he wants a relationship with you. He must be able to show it. Click To Tweet

Again, when a man becomes emotionally available after a divorce will vary. Unfortunately, there are no hard and fast rules when it comes to love and your heart. I wish there were! However, there are some signs to look out for. Can he talk about his emotions openly? Does he talk about his divorce less and less? Can he discuss and follow through on long term plans with you? If the answers are yes, then it is more likely that this man is ready to find long-term love again.

9. Is he too quick to commit?

You may be saying to yourself: isn’t it a good thing that this man wants to commit to me and our relationship? Didn’t you tell me this was a sign he was ready? Yes and no. Hear me out. I promise that this is true. Moreover, when I’ve mentioned this theory to other single friends they’ve agreed with me, so it is extra field-tested.

Someone who was married or in a committed relationship for an extended period most likely enjoys being in a relationship. This separated man is used to having someone to go out to dinner with, discuss life’s problems, news, or travel. They like these aspects of a relationship, even if, at some point, they stopped loving their spouse.

Being in a relationship, even if it’s not a great one, also provides security. It means that you never will go to a wedding alone. Your emergency contact isn’t your mom. Your bed doesn’t feel empty. You have someone to share expenses with. So, when his marriage ends, he may be quick to begin a new relationship to reclaim that feeling of belonging to someone.

However, merely being in a relationship for relationship sake is not good for anyone. First, it is not good for the man, because it is likely that he is in a relationship with someone with whom he is not compatible, just because he wants to have someone fill the space left by the former spouse. At some point, he will realize that this relationship is not for him and will end it, repeating the cycle of sadness and lack of security.

It is also not good for you. What if you think that this relationship has long-term potential only to be disappointed when it fizzles out? What if you struggled to find love and now this relationship has to end because the man wasn’t ready for it. Such a situation can be very emotionally damaging. You will likely be angry and confused. You may feel like you did something wrong, not understanding that the relationship was doomed from the start.

How do you know if this is happening to you? Luckily there are signs. Did you go from the first date to being in a relationship in a matter of days? Does he make future long-term plans (such as taking vacation months from now) early in the dating process? Is he introducing you to friends and family after date two? If you answered yes to any of these questions, you need to take a step back. Is this man here for any relationship or a relationship with you?

10. Is he still angry at his ex?

A person that is still angry at his ex is not ready to be in a serious relationship. Full stop. You will know this right away. Surprisingly, whether a man is still angry with his ex is not always dictated by who left. However, I generally find that my male clients remain angrier longer if it was their spouse who decided to end the marriage. I also see these men stay angrier for longer if they were the victim of infidelity.

Don’t worry. You can spot these types of men in the wild before it is too late. Some warning signs that he is still in the anger stage are:

  • He can’t say her name without venom accompanying it.
  • He calls her names or disparages her appearance or personality traits.
  • He never has anything nice to say about his former spouse, even if it is something benign as she was an excellent cook or excelled at crossword puzzles.
  • Every time he discusses the divorce (which may happen often), he will mention something that she did wrong or how it was all her fault.
  • He never takes responsibility for his part for ending the marriage.

I have experienced this myself. I began chatting with a man on a dating app a few years ago. When I mentioned what I did for a living, always scary for me, he told me he was divorced. I already knew he didn’t have any kids, so it didn’t bother me. However, he then began to go on a tirade about his ex, the lawyers, and even the judge. He kept talking about how his former wife “screwed him” and that the lawyers and the court were “on it together” just to make money. I ended the conversation right then and there. Someone that still has that much anger about his divorce is not ready to be in a long-term committed relationship. If that is what you want, you need to move on from a man like this. Immediately.

Beginning any new relationship is scary. I know it is for me. It is hard to put yourself out there to others, especially if it hasn’t worked out for you in the past. However, you need to make sure that when you embark on a new relationship with someone, you do it with your eyes wide open. It is particularly true when you are dating a separated man, as these types of relationships bring extra feelings and baggage to consider. However, if you are honest with yourself and use these questions as a guide to examine your situation, you will put yourself in the best position to decide if this relationship is a healthy one to pursue.

Elizabeth has been working as a divorce attorney for the last ten years. She’s represented hundreds of men and women going through separation and divorce. In doing so, she has learned a few things about love and relationships. Elisabeth runs her blog The Divorce Lawyer Life, where she shares her knowledge.


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