Ask Wendy

Should I Date the Newly Divorced Guy?

Friday, September 27, 2019
Hey Wendy,

I have been following you for a long time. Thank you for what you provide!

I have a deal-breaker that I won’t date men fresh out of a marriage or long-term relationship (no matter how long they've been miserable in it!) However, I know several women who found their guy just this way!
I believe you did as well?

I have dated freshly single men, and it's been my experience, that they adore me, but aren’t truly available, as they have not worked through singlehood, and their last relationship. I feel like a rebound like they don’t really "see" me, they are just needy. Or, they're still in the messy post-divorce process with the ex. Would love your thoughts on this! Is it too rigid to have as a deal-breaker? If so, how do you vet them?

— Michelle C

Hey Michelle,

Thanks for following me.

I honor your deal-breaker, whatever it is.

I also appreciate your willingness to examine exactly why we have the deal-breakers we have, so well done on questioning yours. We humans are always changing and evolving and what worked last year might not apply today.

I think what’s behind this oh-so-common deal-breaker is fear. Fear of falling for someone hard, then getting the rug yanked right out from under you. You’re trying to mitigate heartbreak before it happens, and who could blame you for that? (Definitely not yours truly.)

When we’re dating, often we’re dealing with strangers, and when you’re connecting with any stranger, there are no guarantees.

You might be wondering, “Why would a newly divorced or separated guy be dating before he was ready anyways? What’s the deal?”

Answer: Because recently separated/divorced men are usually looking for two things: sex and attention. And there’s no faster or efficient way to get sex and attention at the same time than to go out on a date with a delightful, positive person.

Did I meet my guy when he was newly divorced? Nope! He was newly separated—five weeks to be exact.

My BFF and her husband? Six weeks into his separation.

I could keep going, as the list of couples I know that got together from his first date after divorce or separation is long.

Now, before you run off to go hang out at the bar of your local Marriott Residence Suites, allow me to give you a few observations from my research conducted from Newlydivorcedland.

There Are Three Kinds of Newly Divorced/Separated Men

 When you’re looking to date men in their mid-forties and older (most of my readers are attracted to men in this age range), there are three types of men, with some variance within each of these three types.

“I’m free, free, finally free!”

This guy tried marriage and learned it really wasn’t his cup of tea. He found that marriage was a series of compromises and negotiated collaborations that weren’t worth it in his grand scheme of things. For him, the delicious and comforting aspects of partnership didn’t make the trade worth the sacrifice(s).

He enjoys companionship. He craves adventure. And since he loves women, he’s going to work on spending time with as many of them as he can for the rest of his life. When this guy says, “I’m never going to get married again,” believe him.

There is a subset of humans who have unkind things to say about this guy. I’m not one of them. I think he’s awesome. If he wants to be single, date women, and buy fancy whatevers (cars, boats, etc.) that make him happy then that’s his business, just as long as he’s not making any false promises to the women he dates (he can promise whatever he wants to his boats).

“I’m a hot mess!”

When a divorce is sudden and/or he didn’t see it coming, he might be in shock. Or even if he knew it was inevitable long in advance, depending on how he manages the emotional side of his life, it might take him a minute to pull it together and be ready for someone new. His whole world got rocked and he needs to find his footing again.

The hot-mess-divorcee comes on strong. You are the most amazing woman e-v-e-r! You two get “swept up.” And then he has a moment of clarity, which is when you learn you’re the rebound. Most of us have been here more than once, and it feels like being dropped to the ground from a thousand feet in the air.

So, if this is how it goes, why? Why would smart women like me and my BFF be willing to put ourselves through it over and over with the newly divorced/separated guy when this specific category of dating is so painful?

The answer is easy: Not all men.

There’s a third type of post-breakup guy.

“Terrible timing, I know, but it’s you.”

You too have a shot at meeting the newly detangled guy who says, “Wow, I didn’t think I’d meet you so soon.” And boom—done.

How Can You Tell Which One You’ve Got? 

Easy. But it might take a minute. Let’s take a look.

The “I’m free, I’m free, I’m finally free” guy will usually tell you before you can ask. He might all but bring a bullhorn to deliver this message on your first date, or he’ll say so right there on the home page in his online dating profile. “I’m only looking for fun.” “I want to meet new people for adventures.” “Not looking for anything serious.” They’ll tell you. Is there room for exceptions? Sure. But you have a whole lot of vetting to do.

The hot mess might be needy, clingy, or overly reminiscent about his past (with his ex…or the ex before the ex). You might get the sense he doesn’t see you—at all. When he’s looking at you, he sees a mother, a savior, or the fantasy he’s always wanted. He might not have a confident sense of self at this point in his life, so he projects onto you. Or you might get to the we’re-dating part, but you can tell he’s so guarded that he’s not going to let you in or fully commit. These signs will be obvious if you’re willing to see them for what they are—or it’ll become obvious when he ghosts you because you were the rebound.

Alternately, he may take the “showing up but not opening up” path. I’ve had both, more than once. And if I were truly honest with myself, I could have caught even the “it takes time because he’s not opening up” ones much faster if I’d been willing to take off the rose-colored glasses and stop making excuses for him. Eyes wide open, ladies.

Then there’s the “Terrible timing, but it’s you” guys. They both show up and open up. You can count on them to do what they say. They take actions that match their words (in other words, not all talk).They’re not too busy for you. They’re leaning in! Calling, texting, and planning fun new adventures with you.

On my second date with Dave I said, “Wow, you’re really great! It’s too bad our timing is so terrible,” referring to his newly separated status. He replied, “It’s not bad timing for you. The bad timing is on my side. It’s not for you to worry about, it’s mine, I got this.” Hot, right? I sure thought so.

A few more hot things to note about this shade of newly disentangled guy:

  • He knows how to commit and he’s likely willing to do it again at some point
  • He likely “grew up” in his marriage and as a result he’s an upgraded version of himself thanks to his ex and the experiences he had with her
  • He’s realistic about what he needs and what he is able to provide in partnership
  • The fantasy of “happily ever after” without putting in any work is well and truly shattered (good)
  • Bonus points if he has a good relationship with his children: Those little humans have done unspeakable things to and on him, and he still loves and cares for them (that’s staying power!)

Good men who love partnership will find it again, and often quickly. Most women have this fantasy that a guy will wait, mourn, do inner work, heal, take a few personal growth workshops, wait three years, and then go find his new wife. But it doesn’t work that way in the real world. What I see consistently is men connecting with their new forever people either straight away, or after the first rebound (or three) when the old wounds aren’t yet entirely healed, ink still not dried (or even inked yet in some cases), but getting there. These are the men who hold their new person’s hand, and willingly pull them into his future while still doing the work to shake off the past. (Sorry, I don’t create the realities, I just observe them.)

So, what do you think? Still gonna grab your trainers and run away from the newly disentangled guy as fast as you can? Or are you going to give them a chance?

Whatever you choose, good luck!

Do you have a dating, sex or relationship question for Wendy? Send it to Wendy@WendySpeaks.com.