Should You Date a Separated Man?

woma-thinking should I date separated man

Should you date a separated man? Let’s put it this way…

I did. Then I married him.

So, my answer is, Hell Yes!

To be clear, I would never encourage you to go out looking for separated men to date. I didn’t.

In fact, I didn’t notice Larry’s profile said he was separated until I was on my way to our meet-date! As usual, I was time-challenged so it was too late to make a U-turn and cancel.

As I was driving there I was thinking that I was likely wasting my time.

My coffee wasn’t even warm when and the conversation began…

Me: I noticed you are separated. What’s up with that?

(The beauty of dating like a grownup is that you can talk about real stuff. Even awkward stuff.)

Notice I didn’t add any judgments or assumptions to my question. It was just straightforward, open-ended and once I asked it, I shut up and listened very carefully to his response.)

Look, we are not 25 anymore with relatively clean slates. We’ve lived complicated lives, we’ve made bad choices, we’ve got pasts and serious obligations.

There can be many perfectly acceptable (to you) reasons a man hasn’t yet divorced.

Him: Yep, I am. We’ve been living separately for a few years.

Me: Why haven’t you divorced?

Him: I’m not planning on getting married again so I just haven’t gotten around to it.

Me: Oh. I’m dating because I’m ready to get married…when I meet the right man.

Him: Okay. Well do you still want to have coffee?

Me: Sure. I guess so.

Talk about getting our cards on the table, tout de suite, right?

He didn’t go running and screaming when I said the “M” word. And I heard exactly what he said, “I’m not planning on getting married….” NOT “I’m never getting married…” So, I figured that it was worth getting to know him a little bit. Plus he seemed grownup and confident ane kind. I liked being around him.

We carried on with our coffee…

then we had lunch. (Our original plan was to have coffee and “if we didn’t gross each other out” have lunch. Those were his words. Cute.)

Then we had dinner the next night.

I started realizing that being late might have paid off this time!

Look, we are not 25 anymore with relatively clean slates. We’ve lived complicated lives, we’ve made bad choices, we’ve got pasts and serious obligations.

There can be many perfectly acceptable (to you) reasons a man hasn’t yet divorced.

The only way to find out is to ASK and discuss it. Like a grownup. If he contacts you online and you like his profile, ASK. If you meet another way and he mentions he is separated, ASK.

You can say what I did. Or ask “as you’re dating what are you ultimately looking for?” Or “Do you plan on divorcing?” Or even “I have some mixed feelings about that. Can we talk about it?”

Divorce can be expensive and a major hassle. So, for many men, unless they have a really good reason to get divorced (like another woman in their life) they may put it off.

Or maybe his ex is in need of his health insurance benefits that she would lose if they divorce. I’ve heard that more than once and, as someone with a chronic illness, I totally get it. That’s something a good guy does, not an asshole. So, good to know, right?

Of course, there can be red-flags as to why he’s still married. But instead of taking the seemingly simple road and just writing him off…make the effort to ask the right questions, listen carefully and believe what he says. Oh, and share your truth.

There are ways to find out what you really need to know about his past relationships. That doesn’t include asking him why they split up or anything of that sort. You don’t want to dive into that muck, sister.

Instead, use this magic question to get to the meaningful information: What have you learned from your marriage and other past relationships? In other words, what do you bring into the present

Again, I’m not suggesting that you seek out dating a married man. But, when you run into one and he seems interesting, give him the benefit of the doubt until you have a grownup conversation about it.

Maybe your dating a separated man story may turn out like mine:

Larry filed for divorce 3 weeks after our first date.

6 months later I became a first-time bride at age 47. That was in 2006.

So, should you date a separated man? Hell yes! Because you never know.

What’s your experience?  Are you separated and dating? Do you have stories about men you dated who are separated? I’d love to hear from you so leave me a comment!

PS: This is exactly the type of question I help women answer in my Over40 Love School. Being able to make decisions like these is important. If I didn’t know how to answer this I’d likely still be single. 🙂

Over40 Love School is…

a 9-month program for mature women who want to find real love, are tired of the same old silly advice and are ready to get to work and get it done!

Sound like YOU?  The next Over40 Love School 2019 starts in February. Enrollment will be very limited!


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