Can Dating a Separated Man Work? (23 Things You Must Know)

As a formerly separated man, dating us can be tricky.

Can dating a separated man work?

Dating a separated man can work but it comes with real challenges. A separated man is still legally married and will likely deal with a range of powerful emotions that may make him unpredictable and difficult to date. It is best to keep dating casually until a divorce is officially final.

While I don’t recommend dating a separated man unless it is very casual, that doesn’t mean you should never date one.

In fact, keep reading to find out everything you need to know about dating a separated man.

Dating a Separated Man: 23 Things You Need To Know

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You might be skeptical about dating a separated man – and for good reason.

There are 23 things you need to know. Sure, there are good reasons it can actually work. We’ll look at some examples of when it works later in this blog post, but let’s briefly go over these 23 must-know facts right now.

1. A Separated Man May Be More Understanding and Empathetic

A separated man may be more understanding and empathetic to a new dating partner.

A separated man may possess a better emotional temperament when it comes to building relationships with others because he knows that there are some drawbacks to dating him.

This can also make him more patient, forgiving, and understanding of any drawbacks to dating you (such as being very busy with work, children, etc).

A separated man can also learn from past mistakes based on his previous failed relationships that he experienced before getting legally separated from his spouse.

This means he might bring a level of maturity to the table that makes him a better potential partner.

2. A Separated Man Might Not Rush the Relationship

Many guys rush relationships with their new partners by talking about the future too soon.

A separated man will not be as needy or demanding in a relationship.

Since he’s going through a separation and likely divorce, he probably is not ready for something super serious right away.

He’s unlikely to push for the two of you to be exclusive, adopt relationship labels (girlfriend, boyfriend), or talk about your long-term future. A separated man might enjoy taking things slow and getting to know each other.

Of course, this is not to say that he will not want to move the relationship forward eventually.

3. A Separated Man May Be More Independent and Won’t Smother You

Not only will a separated man move more slowly, but he will also move with more flexibility and freedom.

He will want to explore new hobbies, work on personal projects, go out with his friends, and enjoy time alone. You won’t have to worry about him trying to tie up all of your time.

If you’ve ever dated someone who smothered you, then you know it can be very unpleasant.

I remember dating someone who would freak out if I arrived 15 minutes later than expected (with no scheduled plans, mind you). One of my favorite quotes is by Thich Nhat Hanh: “You must love in such a way that the person you love feels free.”

A separated man also wants and needs his freedom.

A relationship can only flourish when both partners take the time to nurture and care for their individual selves. A man or woman should never forget themselves just for the sake of being in a relationship.

4. A Separated Man May Be More Appreciative

By definition, a separated man is facing a crisis in his marriage.

He’s seriously considering divorce and has probably deeply contemplated all that he has been missing from a relationship.

Therefore, he will probably show great appreciation for even simple things.

For example, he might say “thank you” for:

  • Texting him back
  • Holding his hand
  • Giving him a compliment
  • Showing him any form of affection
  • Calling to see how he is doing
  • Listening and validating his feelings

Most of us expect some ( or most) of these gestures from those we date.

However, a separated man might have gone weeks, months, or years without physical affection or compliments.

5. A Separated Man Might Not Want Any More Kids

A separated man might already have kids of his own, and may not want to have any more biological children.

This can be a big plus if you do not want any kids or any more kids yourself.

When you date, many people want to know your thoughts on having kids. For many people, “Do you want any more kids?” is a dealbreaker question.

If you and your separated man agree on not having kids, you’ve skipped a major stumbling block for many budding relationships.

I probably don’t even need to tell you how much money and time it saves not having additional children.

6. Dating a Separated Man Comes With Drama

I’d be remiss if I didn’t go over a few of the major hurdles in dating someone who is not yet divorced.

Going through a separation and divorce can be emotionally draining, confusing, and plagued with drama.

After all, he’s not all the way single yet and can be in the middle of a volatile situation working out custody agreements, alimony, or asset splits… are you really prepared for all of that?

It’s no secret that divorce is stressful and having to juggle everything associated with it may be too much for your relationship.

Plus, there’s always the possibility that his ex may not be super pleased about your presence in her estranged husband’s life – which could lead to more arguments (for him and/or you).

7. A Separated Man Is Often Bitter And Resentful

If a man has just separated from a partner, chances are he’s going to feel bitter and resentful about the whole process.

Whether or not these feelings manifest as acts of petulance is another matter.

Unfortunately, it’s going to take some time for this poor fella to get his heart back on track after all that emotional turmoil, so prepare yourself for quite the bumpy ride.

Unless you are ready to listen to him vent and validate his feelings, you might not want to date a separated man.

8. A Separated Man Probably Is Not Ready for Something Serious

Dating a separated man can feel like an exciting adventure at first, but the truth is that he may not be ready for anything serious.

After all, this could be his chance to take a break from any intense relationships and just enjoy being free.

You might think he’s full of potential and set to start a new, amazing chapter in his life with you, but chances are he’s in it more for the thrill of something new than anything else.

At the end of the day, both of you need to decide what kind of connection you really want before feelings get involved and someone gets hurt.

9. A Separated Man Is Likely In the Middle of a Financial Struggle

Let’s face it: His finances are bound to cause trouble, so don’t expect him to be taking you on fancy romantic dates or buying you expensive gifts.

This dude’s still tied to his ex and her grip on your golden-hearted Casanova’s wallet is probably still pretty tight.

Money talks and his conversation with his ex still echoes loudly in every purchase he makes.

If what you want is someone that can freely shower you with materialistic love, then you’d best look elsewhere in the dating world.

10. He Is Still Legally Married

A word of warning: any romantic endeavor with a separated man is going to come prepackaged with more than its share of challenges.

Despite no longer living under the same roof as his spouse, they are still legally married, meaning that if things don’t pan out between you two and he rekindles things with his ex-wife, then anything that happened between you may now become an eleven-letter word called “adultery.”

This could potentially open a Pandora’s box full of legal issues, angry exes (theirs not yours), broken hearts, and possibly even expensive divorces.

Yeah…dating a separated guy is certainly not for the faint of heart.

11. There Are Different Forms of Separation

Temporary separation is like putting your relationship in a time-out when things get too heated.

It’s an opportunity to take some time away from each other to figure out how to make it work.

On the other hand, when couples reach the point of a permanent separation, they’re effectively giving up on the relationship.

It may involve paperwork and lawyers if they choose to divorce, and can sometimes stand as a better alternative than staying together in an unhappy environment.

When you’re considering going out with a separated man, you want the separation to be permanent.

Dating a man in a temporary separation is asking for trouble.

12. You Need To Know Why He Is Separated

Being aware of any potential ‘red flags’ in your new interest’s previous relationships is critical when deciding to get involved.

If a guy has just separated from his previous partner, asking him why offers invaluable insight into his past and current relationships.

Knowing the reason behind his split can help you assess whether he’s really over her (or other exes) or if it’s just a rebound – which isn’t usually the healthiest setup.

Understanding whether he drifted apart from his other half, was cheated on, or if he did the dumping can really matter.

At best, you’ll understand him better.

At worst, you’ll learn something problematic that helps you avoid a bad relationship destined to fail.

13. His Living Condition Might Be Shaky

Dating a separated man can be hard for those seeking stable and predictable relationships.

After all, we have no way of knowing what exactly his living situation is—it could be unpredictable and ever-changing. He might be staying with a friend while they work out the logistics of their split.

He might have rented a cheap apartment, or he may still live with his soon-to-be ex.

Unless you plan on joining him in his nomadic lifestyle, it’s probably best to steer clear of this kind of risk when looking for a meaningful connection.

14. Figure Out How Long He’s Been Separated

Another thing you’ll want to know is how long he’s been separated.

Generally speaking, you want to avoid dating a man who’s newly separated. He is probably still emotionally raw from the huge upheaval of his life.

Instead, look for guys that are 6+ months into a permanent split.

Better yet, one who has already filed for divorce. The farther into the separation, the more likely the relationship has a chance of working.

With more time, he’s able to process his emotions, get his ducks in a row, and figure out what he wants.

15. His Children Will Come First

You need to accept this fact and be okay with it.

Not only is it the right thing to do, but these kids have already been through some major changes in their lives and they could use an extra measure of patience and understanding during this time.

Plus, if you can show a little compassion towards his kids then he’ll notice and appreciate your efforts.

16. Discover the Type of Separation

There are two types of separations – temporary and permanent.

If you’re considering getting involved with a man who is dating after a separation, it’s important to identify which one he is in before you decide how to proceed.

Temporary separation is typically used as the first step when a couple decides to separate before making any final decisions about divorce.

It’s usually only meant to be a time-out so that each party can assess if they want to work through their issues or call it quits.

On the other hand, a permanent separation typically involves both parties agreeing that they’re done with each other and can no longer live together or continue the marriage – without actually getting divorced yet.

The best case scenario here is that the guy is in a permanent separation with a timeline for divorce.

17. Don’t Give Up Your Life

When it comes to dating someone who is separated (or outright in the middle of a divorce), one of the most important things you can do is make sure that you don’t give up your life.

A common thing I see happening with people who are dating someone in that situation is they forget their friends and hobbies.

It’s great if you’re in love and want to spend lots of time with your new beau, but settling into a couple’s rut for months or years on end will not end well.

Your friends need some TLC and your hobbies need tending to – otherwise, you’ll feel foolish if things don’t work out.

18. Don’t Rush the Relationship

It can be tempting to rush into getting serious right away.

This can be especially difficult if you have been single for a while—you might not realize that a divorcee’s situation requires patience and caution.

Remember that they are often dealing with strong emotions, legal challenges, and all the other issues that come with ending a long-term partnership.

Taking things slowly will give them the time they need to get comfortable with moving forward and healing from past hurts.

19. Avoid The Pressure of Relationship Labels

No matter how strongly you feel for each other, don’t put labels on the relationship.

Definitions like “boyfriend” or “exclusive dating” can stack stress on top of what is likely already an extremely stress-inducing situation.

Enjoy getting to know each other, taking things day by day, while understanding that there is no need nor obligation for any titles.

Labels often bring unspoken expectations that can easily derail your best intentions.

20. Keep Things Casual With a Separated Man

Serious relationships require even more effort when one of the partners is going through such dynamic life changes.

Make sure you are both comfortable with keeping things casual until both parties have personally worked out where they currently stand in their lives as individuals before exploring further possibilities together as something more than friendship.

That’s why I strongly suggest that you keep things casual until the divorce is final.

21. Don’t Over-Invest Emotionally

If you choose to date a guy going through a separation, it is important not to invest too much emotionally in their situation.

Over-investing emotionally in these situations can lead to stress, disappointment, and heartbreak for both parties involved. There will be messiness surrounding the separation.

I repeat: things will get messy.

A successful relationship in this situation requires both partners to approach it with patience and understanding for each other’s circumstances.

22. They May Go Back To Their Spouse

With time, separated individuals may decide that their original relationship was worth saving after all and return back to their spouse.

While it can be heartbreaking when your partner decides this, remember that it was their decision and ultimately must be respected.

Being prepared for any outcome will help prevent disappointment later on, so try and keep a level head throughout the dating process. After all, a separation is not a divorce.

It’s essentially a “break” in a marriage.

And many people do try to work things out before getting a divorce.

23. Dating a Separated Man Almost Never Works Out In the Longrun

Dating a man going through a separation is rarely a good idea.

Even though it may appear that he is free and ready to start a new relationship, more often than not it doesn’t end well for the new partner. This is even more true when someone has been attached to someone for many years in a serious relationship such as a marriage.

There are typically many emotional issues unresolved, meaning conflicts can easily arise which can ruin the new relationship.

My advice would be to take things lightly – have fun and enjoy yourself but don’t expect too much from the situation.

Chances are pretty good that it’s just not going to work out in the long run.

Dating a Separated Man: Problems

I bet you also realize that dating a separated man comes with a few downsides.

  • Trust issues due to the history of their separation
  • Difficulty establishing a secure relationship since his marriage may not have legally ended
  • Potential legal ramifications if dating leads to marriage
  • Discomfort and awkwardness may arise while they are in the process of separating from their wife
  • Lack of commitment from either partner
  • Possible judgment from family and friends about the morality of the situation
  • Fear that he might reconcile with his wife rather than being fully committed to you
  • Possibility of him not being financially independent of his wife yet
  • Feeling guilty for any problems between them caused by the relationship
  • The unpredictability of the entire situation.

Can dating a separated man work? Yes, but it won’t always be easy.

Separation and divorce are often ugly times. Few people express their best selves in the midst of life upheaval. As someone dating a separated man, you’ll generally need huge patience, understanding, and grace.

Signs a Separated Man Is Ready To Date

If you want to date a separated man, you want to know if he is ready for a new relationship (however casual). The last thing you want to do is invite heartache into your life.

So, here is a list of signs that a separated man is actually ready to date you:

  • He is happy by himself
  • He does not constantly talk about his spouse or ex
  • He is in good shape financially
  • He can express his emotions
  • He is not overly emotional
  • He is clear about his dating intentions (casual, exclusive, long-term, etc)
  • He takes care of his body (exercising and eating healthy foods)
  • He does not talk badly about his spouse or ex
  • He doesn’t hesitate to date you
  • He doesn’t hesitate to introduce you to his friends
  • He doesn’t try to hide his relationship with you
  • He is emotionally available to you

The most important sign is that he is actively taking steps to move from a legal separation to a divorce. Dating a separated man who doesn’t know what he wants is a sure path to trouble.

Can a Separated Man Fall in Love?

Generally, a man who is separated can fall in love with someone new. A few factors that come into play are how socially active the man is and his current emotional state. Don’t expect instant results.

It can be difficult for a man who is hurt and vulnerable to welcome another person into their life with open arms—especially without feeling the need to retreat or protect themselves.

Their mistrust could make them wary to forge new relationships.

That’s true even if dating feels like an escape from the loneliness.

A lot of men who find themselves alone and dealing with long-term separation will initially feel the instinctual need for comfort and emotional attachment. I would consider that completely natural.

This may eventually lead them to pursue another relationship to meet those needs.

Yet they must heal before there is any room for someone else again.

It’s likely that his previous bond with his spouse is fractured and that he needs time so that he can be fully ready—both emotionally and physically—to connect with you.

The best way to make a man fall in love with you is to tap into every man’s hidden obsession. It’s like rocket fuel for attraction.

Dating a Separated Man: Success Stories

On forums across the internet, users share success stories of dating a separated man. I thought it would be fun to look at a few of these stories to see that sometimes it can actually work out.

Can dating a separated man work? Yes, and here are some stories!

A user called CallLady said:

I’ve been with my separated guy for 18 months now and it’s still working – I’ll call it a true success when he’s fully divorced and we’re still together. Only you can really judge whether it’s worth the risk, separated can mean a whole different thing between one person and another. If he’s completely over the marriage and they’re just waiting to sort the paperwork that’s one thing and I’d be more willing to chance it.

However if he’s still mourning the end of the marriage and going through the emotional fallout from it, I’d stay clear. One thing to think about though is that if they have two kids he’s going to have to deal with his ex to some extent for the rest of his life – if that bothers you already then getting involved with this guy may not be right for you.

On another site,, a user named LuluJ has been dating a separated man:

I have been dating a wonderful man for almost a year.

I’m 26 and he’s 38. On our first date, I asked him if he had ever been married, and he said yes, but that they hadn’t been together for four years.

I assumed they were divorced, but a few months into the relationship, just as things were starting to get serious, he admitted to me that they had never finalized the divorce…There are no kids involved, but they share car insurance which saves them both some money.

They’re amicable, but completely and totally over (according to him).

He told me that he loved me, that I was very important to him, and that he wanted to be available to me, so he was going to get on with the divorce right away…We’re planning on moving in together in December, and he’s said that he wants to be divorced by the time we move in.

George Marris on Quora adds his insight:

I live about 3000 miles away from my ex and we haven’t spoken in five years. I think we will be divorced next year.

My partner is half a world away from her husband and she will divorce him once she becomes a Canadian citizen. Divorce is very complex in the Philippines and timing is everything.

My partner and I have been together for coming up on five years, both of us are only separated.

I think of us as married, our friends think of us as married and frankly, it really isn’t something to worry about. So it worked out great for us. But depending on your particular circumstances, having a relationship with someone separated but not divorced could easily blow up in your face.

Other users on other websites mentioned dating men and women for months or years. Most dating relationships (in general) don’t end in marriage, so success doesn’t necessarily mean a long-term commitment.

You can tell just from these three stories that dating a separated man can work but there are definite complications.

That brings us to the next question: Should you even date a separated man?

Should You Date a Separated Man? (Answered by Experts)

Even though dating a separated man can work, I don’t suggest it.

When a man is going through a separation, he is usually off-center from his life.

He’s often in the middle of an emotional maelstrom, probably in a bad or unhealthy marriage, and legally still very connected to another person.

I’m not saying you shouldn’t ever date them or that you should rule them out completely. That’s not the case at all. However, you should be extremely careful, patient, and go into it with eyes wide open. Dating a separated man is more difficult than dating a single man.

You might want to consider keeping your expectations casual until the divorce is final and the man has fully processed the emotional fallout of ending a marriage.

Even if he checked out years ago (as I did in my first marriage), there will still be emotional and psychological repercussions.

Here is a video that shares another point of view:

Video by Nicole Moore via YouTube—Can dating a separated man work?

Final Thoughts: Can Dating a Separated Man Work?

Dating a separated man can work if you understand his situation, if he is completely over his spouse, and taking active steps to get divorced.

It’s also helpful if you know and use the best relationship strategies for triggering an almost irresistible attraction toward you.

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