If you are on the dating scene, you will likely encounter potential suitors divorced or separated from their spouses. Perhaps you are already involved with a guy and wondering, “Should I date a separated man?”

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. 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. 

Everyone deserves a second (or third, or fourth) chance at love and happiness, and there are plenty of dating a married but separated guy success stories. However, you cannot go into these relationships without recognizing that dating a separated or divorced man is different than dating a man 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 cannot 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. This is particularly important if you are looking for marriage.

If a divorce action hasn’t been filed, it may take years until he is officially divorced. Research in the United States found that, while most separated couples divorce within five years, only about half do so by the one-year mark. Do you really have the patience to wait?

If you are dating a separated man, you should find out where he is in the divorce process. This is particularly important if you are looking for marriage. Click To Tweet

Second, the stage of his divorce may signal whether he is serious about moving on and getting 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 this separation is not severe or permanent. He may not want things to change if he hasn’t even moved out for a trial period.

Many couples separate for a short period, 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 eventually leading to a permanent dissolution, or is it just a bump in the road of his marriage?

When you get the sense the man is not serious about leaving his wife, you should move on before you get deeply invested. Getting caught in the drama between him and his wife is not anywhere you want to be.

For some, dating a man who is separated but technically still in a marriage may be against their religious beliefs or moral values. Sleeping with a separated man can be seen as sleeping with a married man, and that’s one of the big disadvantages of dating a separated man.

As an attorney, I know how long it can take to resolve a divorce case in the court system. Therefore, the fact that the ruling is not yet final is not enough for me to pass on dating a separated man. Instead, I would examine whether he is taking active steps to end his marriage to signal whether the relationship has any future potential.

2. Does he have children?

Dating a separated man with child custody commitments adds another 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 in a place 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, you should probably not be dating someone separated with children. There is nothing wrong with that. Don’t feel guilty. It doesn’t make you Cruella de Vil. 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 impact your relationship. His children, who depend on him, will 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, especially if your partner and his wife are freshly separated, the children may still be dealing with a lot of emotional baggage. It’s undoubtedly a difficult situation for them. Even if you aren’t the woman who broke up their parents’ marriage, they might assume you had something to do with it, and they may not be interested in hearing your side of the story.

In such a relationship, his ex isn’t just his ex — she’s his 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 work hours, and my concern is that I will have to take off my girlfriend’s 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 kids are not dateable. They certainly are! For example, he and his ex may have a healthy relationship and completely respect each other as co-parents. If so, go for it! You need to assess the 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 you will meet will likely have only been in a marriage once, mainly if you are dating in your 20s, 30s, or 40s.

However, there are some guys out there who have burned through several marriages. Before getting involved with a man going through a separation from his second or third wife, 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. If both of the guy’s previous marriages ended because he cheated, chances are that he will do the same to you. He’s the leopard. See his spots.

If both of guy's previous marriages ended because he cheated, chances are that he will do the same to you. Click To Tweet

Conversely, maybe his first marriage was a youthful misstep, and the second failed because of circumstances beyond his control — maybe his wife flipped out and decided to run off with her so-called twin flame! In this case, I would undoubtedly consider dating this person.

I’ve had many clients who match this example. They are wonderful men looking for love for the right reasons. 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.

Other marriages quietly fizzle out to the point where the spouses are merely roommates and no longer lovers or friends. In this case, where there’s not a lot of drama or hostility, committing to divorce might not seem urgent, but both parties will probably understand the reason. People who have challenges are typically aware of them.

In some cases, however, one person is blindsided by the other’s sudden decision to end their union.

One of the biggest factors regarding whether you should date a separated man is how his marriage ended. 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. I would forgive anyone who has a moment of anger at such a vulnerable time if it is not indicative of his general behavior or demeanor.

My best advice is to listen closely if his marriage ended without warning, as that’s more concerning. If he initiated a surprise split, does it indicate his failure to communicate in general?

Furthermore, his ex may hold out hope for reconciliation if she didn’t expect to break up, so her jealousy could be an ongoing source of ugly drama that you’re better off without. If you’re dating someone separated but not divorced, she legally has a point that you’re with a married man! You may prefer a guy who doesn’t have the emotional baggage of juggling two women.

Communication is key to any relationship. If he has difficulty expressing his feelings, particularly unhappiness and lack of fulfillment, how will that be different when he gets together with you? I don’t see the pattern changing unless he has sought professional help.

If his spouse ended the relationship, what are his feelings about how it ended? Is he still in shock? Is he angry? A man in those stages is in a fragile, unstable place. Especially if you’re dating a recently separated man, he may need time to process what happened without being pressured to embrace a new partnership.

There is no harm in maintaining a friendship with this man if you enjoy his company. However, don’t sideline yourself from the dating game because you are waiting for him to be ready. A relationship with a separated man shouldn’t be rushed.

Processing a divorce takes time, and it is different for everybody. Some clients are ready to move on within months, while others take years to work through their pain. 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 varies, and the reasons they end may also vary. 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 with a lack of personal responsibility regarding how one’s actions affect their spouse and, thus, the relationship. However, the demise of a marriage is usually not one-sided.

Both parties typically have a role to play in the failure of their union. One of the most important signs a separated man is ready to date is that he is completely accountable for his share of the problems in his previous relationship.

If you are dating a separated man, you should know why the marriage ended, 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 it.

Most marriages end with a lack of personal responsibility regarding how one’s actions affect their spouse and, thus, the relationship. However, the demise of a marriage is usually not one-sided. Click To Tweet

If the man was the party at fault, he might not want to tell you what happened for fear that you would 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 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 blame for what caused the separation. 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 also happen in your relationship.

6. What is his financial situation?

Relationships should be about love rather than money. However, it’s a reality that finances dictate our everyday choices. Therefore, you should consider the status of your partner’s finances when deciding to begin a relationship with him.

There are some unique financial issues when dating a separated man. First, he is likely to pay child support if he has kids. How much is he paying? Can he afford it? If you were to marry, such expenses might affect your lifestyle. These are some of the most important questions to ask a separated man as you get serious about your attachment to him.

Beyond basic child support obligations, there are other expenses for children to consider, such as tuition, childcare, and after-school activities. Are you okay with having these obligations affect your life and your financial goals?

Second, if this legally separated man is not yet divorced, he may be in financial limbo. Likely, he and his ex-partner haven’t decided how to divide their assets. There’s a risk he may need to pay her alimony in the future.

Also, especially in the United States, there can be complicated situations involving health insurance coverage that keep partners legally attached long after they’re done being emotionally attached.

If your guy has insurance challenges with his separated wife, you could be dating someone who is still legally married for a long time. He and his wife might accept that their lives are connected on this level indefinitely, regardless of how much space they try to put between their lives, so you may need to be realistic about the boundaries you can live with.

Financial insecurity is difficult for people, particularly men. The uncertainty about his life and financial situation after the divorce may affect his ability to commit to a long-term relationship.

Third, separated people often find their finances in dire straits during and after a divorce because they have to pay lawyer fees, spousal support, and other related expenses. A legal battle can result in tremendous debt with ongoing repercussions.

Here, it’s necessary to be honest about your expectations for your future and ensure the guy you are considering is on the same page. Are you looking to buy a house or save for your retirement? If he can’t contribute to those goals because of a financially draining breakup, your ability to reach those milestones may be at risk.

7. Do you both have the same relationship vision?

Not everyone wants a house with a picket fence and two kids. Sure, many consider marriage and having a family their major life goals. Others prefer commitment without marriage or only want to hook up 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. His emotions are probably all over the place if he is newly separated from his previous relationship.

A relationship with a separated man has this risk of being unstable. He may not know what he wants because he is in the middle of one of the most significant transitions in his life. 

Whether or not you’re seeking husband material, you can help by clarifying the type of commitment you’re ideally looking for. However, if you know what you want, and this guy cannot tell you what he wants, the reality is that you may not be compatible relationship-wise at this time, regardless of how well your personalities mesh.

While waiting for him to sort out his life is an option, be aware that he’s dealing with complicated family matters that don’t have easy solutions. Leaving and moving on after a separation is not as simple as it sounds!

8. Is he emotionally available?

Okay, you know that you need to figure out what relationship this legally separated man wants. However, what he says is not as important as how he behaves.

One of the most important ways for your love interest to show you he’s ready for commitment is to be emotionally available. It means that his heart and mind need to be open and ready to trust a partner and find love again.

Divorce and separation are scarring. They make people put walls around their hearts and never show vulnerability again. Is his wall still up? If so, no matter what you do or how awesome of a partner you are, the relationship will not work out.

Can a separated man fall in love? Again, when a man becomes emotionally available for a new partner after separation will vary. Unfortunately, there are no hard and fast rules regarding love and your heart. I wish there were!

Although he may never be the same man he was before his previous relationship, there are signs he’s opening up to the possibility of a serious future relationship.

Can he talk about his emotions openly? Does he talk about his past marriage less and less? Can he discuss and follow through on plans with you? If the answers are yes, this man is more likely to be ready to date again.

9. Is he too quick to commit?

You may say, isn’t it good 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 mentioned this theory to other single friends, they agreed, 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 to dinner with, discuss life’s problems, and travel with. He may miss these simple realities of life with two people, despite whatever led him to part from his ex-wife.

Even an imperfect relationship 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.

A freshly separated man may quickly begin a rebound relationship to reclaim that feeling of belonging to someone. If he’s not entirely over his wife, he might even start a rebound to provoke her jealousy of other women and make her realize she’s still capable of feeling attachment to him.

Of course, merely being in a relationship for the sake of being in a relationship is not good for anyone. This is one of the biggest dangers of dating a separated man.

First, it is not good for the man because he is likely 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. Eventually, he will realize that this rebound relationship is not for him and will break it off, repeating the cycle of sadness and lack of security.

It’s also likely to hurt you. What if you think this relationship has long-term potential, only to be disappointed when it fizzles? 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 leave you upset and confused. You may feel like you did something wrong, not understanding that the relationship was doomed.

How do you know if this is happening to you? Luckily, there are obvious clues that you might be just a rebound. Did you go from the first date to being in a relationship in a matter of days? Does he make future plans (such as taking vacation months from now) early in the dating process? Is he introducing you to friends and family after date two?

You need to step back if you answered yes to any of these questions, which are huge red flags. Dating a separated man is a journey with more than its share of complications, so it’s best to take things slow and give him plenty of time to deal with his emotional baggage. That way, you’ll have an opportunity to find out if he is truly ready to make an emotional connection with you his priority.

10. Is he still angry at his ex?

A person 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 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. When even her skills at cooking or crossword puzzles get twisted around into a way to say something bad about her, it is one of the more subtle red flags to be aware of.
• 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 in 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, which was always scary, 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” to make money.

I ended the conversation right then and there. Someone still focused on his anger about his ex is not ready to be in a long-term relationship.

When red flags of this sort are present, you need to move on immediately. He may even tend to view all women through the lens of his feelings about his wife, making it impossible for him to understand your perspective fairly.

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, ensure that when you embark on a new relationship with someone, you do it with your eyes wide open.

These key pointers are especially important when dating a separated man, as these relationships bring extra challenges and complications to consider. You have to look at the practicalities and ensure you are on the same page with him.

However, try to be honest with yourself and use these questions as a guide to examine your situation. In that case, you will put yourself in the best position to decide if this relationship is a healthy one to pursue.