Dating After Divorce Cheat Sheet

Dating After Divorce Cheat Sheet: The 5 Types of Men You MIGHT Meet

Dating after divorce can be frustrating. While you might remember what dating was like before your marriage, the men you meet after divorce are in a different ballpark—if, they are even in the game. Among them, those who are truly viable, you’ll find a differing assortment of good and bad. The problem is if you haven’t dated in twenty years, you have little context by which to compare the good against the bad.

As well, and far more interesting is the fact that you’ve grown—not only in age but as a result of your divorce. You’ve learned the only way to really appreciate the nuances of the goodies and the baddies (beyond and between the simple profiles offered below) is to dip your toes into those dating waters and to bear a few things in mind.

It’s an attitude, so practice it

Dating after divorce is a wonderful way to experience life anew. But don’t take your dates too seriously. Instead of looking outward for the “One” or “The Only,” invest in having fun and getting your bearings. We caution you about jumping into another long-term, committed relationship.

Instead, get a good feel for your wants, needs, likes, and dislikes. You will want to understand yourself first and learn how to stay true to you in your next relationship—if you even choose to have a next relationship. (Maybe you just want to focus on healing right now? That’s okay, too.)

If you are open to the idea of dating after divorce, though, we’ve prepared the following cheat sheet on the five types of men you might meet so you can be prepared. While we know there are a lot of great men out there, we also know there is truth in jest.

The Misanthrope

This guy is cheap—and we’re not saying cheap as in he’s not picking up the tab for the date (feminism means splitting the bill, right?). No, he’s the extreme sense of squeak—frugal with money and his time, and, sometimes, even his emotions. He’ll seem attractive at first because he’s elusive, and when he shares, he sounds so sensible. He believes in equality, “partnership,” and the mutual sharing of finances. But after a few early bird-dinners where he’s pulled out his calculator (not on his phone, but from his pocket), or your needing to negotiate his penciling you in on a Wednesday, next month, his mystery fades.

He distrusts people, and for that reason, he is loathe to invest. Are you up to the task of teaching him you are deserving and worthy?

The Monologist

Read about him here, because chances are you’ll never get a word in edgewise when you meet (your next?) Monologist. This is the type whose internet profile leads with his professional title . . . “Lawyer,” “CFO,” “Surfer.” In person, there is never any awkward silence because he fills the air sharing about himself. When you start to chime in, then dare to add a thought, you’ll suddenly be corrected (a mixed bag, because at last he’s heard you and you’re rather touched but then chastened). The word you chose to enunciate is not right. No, let him explain. And more mansplaining takes place.

Been there. But you are working on your capacity for compassion. So you let the leash run and run—to make sure he’s not as egregious as he seems. He can’t be.  He is.

Out on the street you tell him, it was lovely meeting but you don’t think it’s going to work out. Call you crazy, but you’d like a companion who asks you about yourself.

The Peter Pan

Ah, Sweet Bird of Youth! Whether he’s actually younger than you, or just at heart, his energy and attitude are so refreshing. It’s exhilarating to be with someone who’s positive, who’s au courante with happenings, and who thinks you’re cool enough, too.

Peter Pan knows the latest, latest. His fingers fly quickly across his smartphone, showing you the video of the next place you should go, you must go, it’s this club where this band he loves is playing! Peter Pan takes you to a bar where, as you look around, you notice there are only young people. Very young people who know him very well. A couple of nubile beauties sidle up to Peter Pan, and he looks at you as if to brag. You watch his arms slide comfortably around them. He’s their mascot. He’s either their seasoned, slightly older social director, or he’s their tired, tragic mascot. You are trying to decide which, when he offers to get you a drink and take you backstage “to meet the kids.” You’re excited because you get to use a word you’ve just learned, “Nolo.” And out the door you gogo.

There’s a reason this guy is so on the pulse to what’s young—he’s never grown up.

It’s also why he might be divorced. And if not, if he’s never been married, ask him if he’s big into video games.

Youth and energy can be fun, even confidence boosting, but problematic when you’re in trouble and need a hand. Says one client formerly married to a Peter Pan:

“I just got sick of being his mother, too, of being the killjoy, the heavy always explaining to the kids that we couldn’t do what daddy was wanting because we didn’t have the money. I wanted to be the fun one, sometimes. I am working on that now!”

Mr. Plug & Play

This guy is committed. He’s really really pro-commitment. He’s looking for a “LTR” (a long-term relationship) he tells you, more than once. He seems in love with the idea of being paired-up, and you (without his knowing the least thing about you) are perfect for him.

At first, Mr. PP seems amazing because he’s so into you—he’ll hang on your every word. He’ll even listen, with that latter part making you swoon. But soon, he’ll declare, to you, to the universe, how amazing it is that you and he are exactly alike.

Except you are not.

You are open, curious, but cautious, checking him and the situation out.

This guy, on the other hand, has already plugged you into a life he created a long time ago in a galaxy far, far away.

If this guy is below 40, he wants desperately to be married, for whatever ambitious, personal or cultural reasons.

If this guy is 40 or older, and recently divorced, it’s likely he’s looking for his Ex’s replacement. He has done no work on himself. He’s seeking to partner up because being alone is so darn uncomfortable. He likes it when the house “is neat and organized and there’s someone there to fix his meals.”

“I felt like the missing piece to his jigsaw puzzle,” sighed Olivia. “We had not even ordered drinks when he started telling me about his needs, what he was missing. He told me, point blank, that he was looking for someone to take care of him in his old age! It wasn’t a date, it was an interview, just showing me again how insidious this white male privilege is. They are clueless.”

We think we can all agree that if you were interviewing for a job, it would be good to know the salary and benefits paid.

The Mr. Darcy

Little by little, this guy seems like the complete package—Mr. Darcy is sensible, proud, and yet, capable of cutting loose. An added boon is that he treats you with respect. He makes you feel feminine. Special somehow. But he doesn’t tell you everything about himself that first night. He actually asks you questions as a way of deflecting your questions you pose to him.

The Mr. Darcys of the world have been burned in the past and may come off as overly cautious or guarded. Maybe he’s been divorced, too. Maybe his best friend betrayed him, or maybe his Ex betrayed him with his best friend? This guy has so many walls up, you might not actually be sure he likes you until he breaks down and confesses all his thoughts, his feelings in a gushing romantic speech many dates later.

Maybe. Or maybe you just saw that scene on Netflix.

However, there may be just enough there to keep you wondering. You are not certain, but you think you might give this guy another date, if only because you know one thing sure about yourself. You absolutely stand with and for second chances.

In Sum

If you have the ability to have these experiences and muse with your girlfriends, then, each of these encounters was worth its weight in wine. On the other hand, you may not meet any of these men. Any which way, our experience with women after divorce suggests, it’s important to be mindful of OUR desire to couple up. Too often that “need” leads the show and can blind us from seeing who is really seated across the table. We encourage you to cultivate your particular perspective, to balance the desire to get out there again with the opportunity it is for you to look at yourself.

And by the way, our vote would go for Mr. Darcy. He’s the most promising according to the book.

Since 2012, smart women around the world have chosen SAS for Women to partner them through the challenging experience of divorce and recreation. Now you can secure female-centered support, information, and next steps if you are rebuilding your life with Paloma’s Group, our virtual, post-divorce group coaching class for women only.  To promote sisterhood and protect confidentiality, please know space is limited. Visit for details.

“I am so happy to have these sisters on the journey with me! Our connection is very productive, very powerful. We’ve met each other with a warm full heart! I feel understood — at last — because I know these women get it! They are going through the same thing. Our connection has ended any sense of isolation or alienation that on and off, I’ve been struggling with.

Thank you for bringing us together and creating Paloma’s Group!”

~ S.L., New York City

Share these insights


  1. Brandie on April 16, 2020 at 21:21

    I’m meeting a man

    • SAS for Women on April 17, 2020 at 08:43

      This is VERY exciting! Just be careful about social distancing depending on where you live. It will be better to keep this a virtual affair until the outside world is safe.

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