21 crucial things to know about dating a separated man

Dating a separated man comes with its own unique set of challenges.

I know this first hand.

Last year I started dating a separated man. And I’ll be honest, it hasn’t been the easiest ride.

We’ve made it out the other side now (I hope) and are still going strong. So in that sense, maybe I’m one of those dating a separated man success stories.

But there are some things I wish I’d known from the start that I had to find out the hard way. And there are some mistakes I made.

I’d like to share them with you in the article in the hope that they help you navigate your own situation dating a separated man.

My own story of dating a separated man

On our first date, he didn’t tell me about his wife. That in itself could be a red flag. But I also do understand why he didn’t.

He wanted us to get to know each other just a little bit before dropping that bombshell. It was perhaps a bit calculated. But when is the right time to mention you technically have a wife?

If I had known from the get-go, I’m not sure I would have gone ahead with the date even. It was one of my unwritten rules: ‘never date a separated man.’

It wasn’t until we were texting later after the date that I discovered he was living in a hotel apartment.

Er, why? was the obvious question I wanted to know. “It’s a long story”, was his reply. Not long after he followed that up with an “I’m separated and haven’t found a permanent place yet.”

Is it OK to date a man that is separated?

This was the question that instantly ran through my mind: is it OK to date a man that is separated?

His marriage is over and I had nothing to do with that, so morally I felt in the clear. Plus I really liked this guy.

But why then did I feel so bad about it?

I think probably because on some level I knew it made things messy. And I wasn’t sure whether I wanted to put myself in the middle of all that.

And that brings me nicely to the very first consideration on the list that you need to think about when dating a separated man. So let’s dive in…

Dating a separated man: what you need to consider

1) Is this really worth it?

Very early on, ideally way before getting attached, you have to ask yourself is this really worth it.

Is HE really worth it?

Because if he isn’t your dream guy then I’d say there are going to be way easier relationships waiting out there for you.

You don’t want to end up being disappointed or hurt by him. Before you get in too deep, you really need to figure out whether you can just walk away now, or whether you feel compelled to stick around.

When you’re not as invested in how things turn out, you might not see the harm in just seeing how things go. But further down the line when the complications start to mount, walking away won’t feel as easy.

We’re only human and growing feelings tend to happen no matter what.

If you can’t see it lasting in the long run, then you might want to reconsider whether you’re better off backing off whilst that is still an easy option.

2) Is he really separated?

I ask this because that was one of the biggest questions and concerns I had going into it.

Some of my friends questioned whether he could be lying to me. But my point to them was that if he was going to lie, why not totally lie about having a wife in the first place.

Why not just say he was single. I believed he was technically separated, but was he really SEPARATED separated?

As in was this definitely a forever, on the way to divorce thing, or was it a trial period?

Was his marriage 100% over, or was there even at least 1% chance they could work on things.

The reality is that you will have to accept that you can never know for sure. You can only ask, and figure out whether you believe him or not.

There’s no getting away from the fact that dating a separated guy comes with a risk. You could invest in him, only for him to turn around and work things out with his wife.

All you can do is do your due diligence and find out where in his separation he is at.

3) When did he separate?

Where he is at in his separation (and healing journey) will most likely depend on when he separated.

Time is a healer, and so the longer it’s been, the better.

His head is going to be all over the place if the separation is very recent. Also, the longer it has been the more likely it is that this really is a permanent move, rather than a trial.

But even this on its own isn’t going to be so clear-cut.

In my case, it wasn’t so great. It had only been 3 months since he moved out. But he assured me that the marriage was well over long before that.

His unsteady lifestyle and living arrangement, coupled with the short period of time he had been separated for set alarm bells ringing.

But in the end, I took into consideration mitigating factors when I found out why he separated.

4) Why did he separate?

Why is he separated? What problems did the marriage have? How did he contribute to them? And how did he try to repair their marriage problems?

This might sound as though you are asking a lot of very private questions that you may not feel entitled to ask.

But the reality is that you need to know. Because his answers will give more insight into how messy his breakup has been, and the type of man he is.

If his marriage fell apart because of his infidelity, you don’t need me to tell you that’s not good news.

If he didn’t try very hard to make the marriage work, then again — not great.

If he ended the marriage and his wife was against the separation, don’t expect her to walk away quietly.

If she ended the marriage and he didn’t want to, then he is more likely than not still invested in that relationship.

In my case, they had been together since they were very young, had grown apart over some time and he came to the conclusion that it just wasn’t working anymore. Which she accepted.

5) What is the living situation?

I appreciate that separation is expensive. Divorce is not only emotionally draining, but also financially too.

He may say that he lives with his ex still because they just can’t afford for him to move out just yet.

Despite how legitimate that may be, it makes things a million times more complicated. And I’ll be honest, I wouldn’t go anywhere near that situation.

Can you trust him to live under the same roof as someone he has such a strong history with? How much more insecure and jealous will that make you feel?

The answer is: probably quite a bit.

It would be one thing if he lived alone. But having him live with his ex? That’s a whole different ball game.

6) Does he have children?

Kids undoubtedly complicate things even more. If you are dating a separated father then you need to accept:

These aren’t easy facts to have to swallow. But they are true.

Of course, it’s not impossible to navigate, and his children can come to enrich your life and your relationship together.

But it’s one more important piece of the puzzle that you will want to think long and hard about.

Disadvantages of dating a separated man

7) Your patience might be tested

There are going to be many things — sometimes big and sometimes small— that can test your patience when dating a married man.

You will need to be patient in the speed you grow the relationship, patient over his residual feelings, and patient over the timeframe of the divorce.

Things will crop up that you didn’t even think about. I’ll give you an example from my own situation:

One night a few weeks into dating his phone was ringing constantly. He ignored it. We continued our date.

One thing led to another, and we ended up in bed together. Afterward, he checked his phone again and said to me:

“I’ve got a lot of missed calls from my ex, she never calls so I need to check if something is up”.

After stepping outside to take the call, he comes back in to inform me that she is sick (this is during Covid times) and he has to take her to the hospital.

Several hours later I get a text to say that all is ok, it wasn’t Covid and she is fine now.

I understood his need to leave. I respect that he still felt a duty of care toward his ex. At the same time, did it feel good? of course not.

Be prepared to have extra patience and to put up with some extra annoyances.

8) You might experience jealousy

Separated is not divorced. And as my story above hopefully illustrates his wife probably isn’t completely out of the picture.

No matter what he tells you about his feelings towards her, it’s never simple.

She might not be his priority anymore, but she is still in his life.

His ex is still on the scene, no matter how invisible he tries to make her. And this can cause a lot of insecurity in your relationship.

If he spends any time with her, you’re gonna start feeling like there is something between them.

If he still has to talk about her, see her, do things for her etc, (which he most likely will) then you may well feel jealous.

9) He might not be ready for a serious commitment

What do you want from this guy? Are you genuinely happy to date and see what happens?

Do you know that you are looking for a committed relationship? Maybe you are ready for marriage and kids?

If you want to be settled and committed, you need to ask yourself whether he is really in a position to give you this now?

He has just gotten out of a marriage. It takes time to heal and fully move on. Don’t kid yourself that he will be ready to jump into something serious again right away.

10) You could be a rebound

One of the big problems with being a rebound is that you might not know you were a rebound until hindsight kicks in.

You only realize when it doesn’t work out that he was trying to fill the gap that was left in his life with something (or in this instance someone) else.

He may not even realize he is doing this. Rebounds tend to be defence mechanisms so that we don’t have to feel the full extent of the pain and sadness of a breakup.

There can be some clues that you are a rebound:

  • How long it’s been since they broke up
  • If he jumps fully into your relationship, love bombing you from the start.

Particularly with the latter you have to question why his feelings seem so strong so soon. Maybe because he is looking for a hiding place, and has found it in you.

11) His life is unstable

Anyone who is separated is going through an unstable stage of life.

That instability can show up in practical and financial ways, it can also be an emotionally unstable time.

His living arrangements might be unstable, his finances might be unstable, his feelings might be unstable.

And your life will become a little bit more unstable as a consequence.

So if you decide to go ahead with this relationship, be aware that you may be dealing with a very unstable person at this point in his life.

12) People might judge you

One thing I didn’t really consider was how others might judge.

He’s a free agent BUT if he’s still married, be prepared for some disapproving faces.

Some people may disapprove of you going anywhere near a guy who is still technically married.

Personally, I have very open-minded friends, but that still didn’t mean I didn’t face judgement.

Some friends acted like I was being an idiot. They were just worried for me. But they didn’t trust that any of it was a good idea.

There were too many things that could go wrong, and they didn’t want me to be in the middle of it all.

13) He could be playing the field

If he is recently separated he might be enjoying his newfound freedom.

After feeling “tied down” for some time, plenty of separated guys go through a stage of wanting to sow their wild oats again.

After all, sleeping with a separated man is not the same thing as being in a relationship with him.

Are you exclusive? Is he seeing other people? Are you ok with that?

You need to ask these things and be honest about what really works for you. Don’t assume that sex will lead to a relationship if that’s what you are hoping for.

14) He might have emotional baggage

An important ground rule for dating a separated man is to remember you are not his unpaid therapist.

That might sound harsh. You certainly will need to lend a sympathetic ear from time to time. But do not take on board his baggage.

He needs to be the one to unpack it. You will have to be patient whilst he does. It can mean he carries certain hangups, issues and pain into your relationship.

He is probably more fragile as he’s been through a lot.

We all have some emotional baggage, but that of a separated man can be greater.

15) You could have a long road ahead before he is truly a free agent

Regardless of how long he has been separated, you probably still have a long road ahead of you before he is 100% free and single.

A divorce takes time. It can be very complicated dividing the lives of a married couple. The divorce process can drag out over months or even years.

There will be legal hurdles to overcome. But even when the divorce is finalized that doesn’t mean it’s all over — especially if they have children together.

Don’t be under any illusion that you can instantly and fully disconnect your relationship from his past one. It’s going to take time.

My best advice and tips for dating a separated man

16) Ask plenty of questions

If you’re anything like me, then you may have a tendency to try to play it cool at the beginning of a relationship so you don’t rock the boat.

Often we don’t want to “scare someone off” by asking the big questions. Sometimes we also are scared to ask in case we get an answer we don’t like.

But you need to ask all the important questions. Your heart is on the line.

If there is anything you feel doubt over — ask.

If you need him to clarify anything — ask.

If you need reassurance — ask.

If you’re going to do this then make sure you put good communication at the forefront of your relationship.

17) Don’t ignore red flags

This goes for all relationships really, but red flags when dating a separated man should never be swept under the rug.

If your gut tells you something, be sure to listen.

If alarm bells ring over something he says, does, or around his situation — then do not ignore the warning.

18) Take things slow

Only fools rush in. It’s easy to let feelings carry you away, but you might need to show some restraint to make sure the relationship progresses slowly.

That allows you to work out any issues, and get to know one another in your own time.

Some relationship experts recommend only seeing each other once or twice a week anyway in the early stages of dating.

That way you don’t find yourself getting attached too soon before discovering it’s really not going to work.

19) Be clear about what you want from him

Get clear in your own mind, what you want out of this?

You should decide if it’s just a situationship or a bit of fun, or if you want it to go the distance.

Once you know yourself, be honest with him.

Ask him what he wants too.

Now is not the time to make a complicated situation worse by not being honest about your needs and wants. If he can’t give you what you want — walk away.

20) Create strong boundaries

Everyone should have healthy boundaries. We need to know what is acceptable and what isn’t.

You need to know your own boundaries and uphold them. They become the rules by which you govern your relationship.

They can also be turned into practical rules that you introduce to your relationship.

For example, one of mine was that I didn’t want to be in the room and overhear him arguing with his ex. Rule: No phone calls to her when we were together.

Your boundaries will depend on your unique situation.

21) Get some expert advice specific to your situation

While this article explores the main things you need to know when you’re dating a separated man, the reality is that every situation is totally unique.

Your challenges are going to depend on the dynamics and pitfalls of your particular circumstances.

That’s exactly why it can be helpful to speak to a relationship coach about your situation.

With a professional relationship coach, you can get advice specific to your life and your experiences…

Relationship Hero is a site where highly trained relationship coaches help people through complicated and difficult love situations, like dealing with the extra challenges that are thrown at the relationship when you’re dating a separated guy.

They’re a very popular resource for people facing this sort of challenge.

How do I know?

Well, I reached out to them when I was going through a tough patch in my own relationship with a separated man. After being lost in my thoughts for so long, they gave me a unique insight into the dynamics of my relationship and how to get it back on track.

I was blown away by how kind, empathetic, and genuinely helpful my coach was.

In just a few minutes you can connect with a certified relationship coach and get tailor-made advice for your situation.

Click here to get started.

Pearl Nash

Pearl Nash has years of experience writing relationship articles for single females looking for love. After being single for years with no hope of meeting Mr. Right, she finally managed to get married to the love of her life. Now that she’s settled down and happier than she’s ever been in her life, she's passionate about sharing all the wisdom she's learned over the journey. Pearl is also an accredited astrologer and publishes Hack Spirit's daily horoscope.

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