Dating a Divorced Woman? Here’s What We Want And Don’t Want

dating a divorced woman

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

Dating a divorced woman? Here’s a story that might help you understand what we want and don’t want!

What Divorced Women Want and Don’t Want From the Men We Date

by Jackie Pilossoph for The Good Men Project

Karen could not have been more excited. After a heartbreaking divorce, several months of quarantining and isolation, and countless duds and nightmares she met on Bumble, the 42 year-old single mom of two teenagers finally came across a man to whom she felt a connection.

Karen and Dave met on Bumble and had a really nice phone conversation. Describing it as “easy, nicely flowing and enjoyable,” she said she loved how Dave paid attention to things she was saying, and that he seemed to really care about her. Karen felt respected, heard, validated, and at the same time, sexy and pretty. Finally, a nice, normal guy. At the end of the conversation, the two decided to meet that weekend.


Bridging the Gap Between Conflict and Resolution


Hanging up the phone, Karen felt overjoyed and energized, with a renewed sense of hope. There were good guys out there! She rushed to her closet to start the search for what to wear to their date, wanting to look stunning for what might actually turn into a healthy relationship.

Happily shifting hangers to the right, weeding out all the dresses and tops that just weren’t good enough for her potential Mr. Right, Karen heard her phone ding, indicating she had a text. Was it him?! Of course, it was! How thoughtful. This sweetie was sending her a cute message about how much he was looking forward to meeting her.



She raced to her phone and hit the message, and that’s when time stood still for a moment and Karen’s jaw hit the ground. She was in disbelief. It couldn’t be happening. There was no way. But sadly, in the world of dating after divorce, there was a way. Promising Dave had just sent her a dick pic. Karen’s heart sank, as she stood there realizing she had to add Dave to the group of horny, dysfunctional, damaged, screwed up divorced men.

Karen is not alone. I’ve been Karen and I know countless other divorced women who have had similar encounters. My question is, why? I’m not saying divorced women are perfect either, but what has happened to the mindset of some divorced men, who think we would remotely be interested in seeing a photo of his naked package before we’ve even gone out on one date or ever, for that matter?

Advice for dating a divorced woman:

Listen, I get it. Everyone wants and needs sex. It’s human nature to crave intimacy, human touch, affection, and of course, love—whether it’s real or an illusion. But come on guys, I don’t know one woman–even those of us who haven’t gotten naked with a guy since 2009, who feels desperate enough to respond favorably to a dick pic this early on in a relationship.


Alyssa Dineen -
Online Dating Coach and Stylist


So, what was this guy thinking? Here are some possibilities. Maybe Dave got carried away in his excitement and thought Karen would appreciate seeing what she could have. Perhaps Dave is bitter or angry with women in general and is subconsciously trying to get back at those who hurt him. Or, maybe Dave’s delusional and thinks his body looks as desirable as it did in college, and that Karen would suggest they get together right now.

The most likely scenario in my opinion is that Dave feels like so many other men and women who spend their nights browsing dating apps:  burned out, tired of rejection, sick of the games, fed up with the online dating profile lying that goes on, and exhausted from being hurt to the point of not even caring anymore.

As much as I feel for Dave and all divorced people who want to find love again, newsflash for divorced guys: dick pics just aren’t cool, unless someone asks you for one.

So if you are dating a divorce woman, you probably want to know, what do divorced women want when it comes to the men we date? Here are 11 things, none of which involve an iPhone and/or the removal of your pants.

Click here to read the rest of the article, published on The Good Men Project

Like this article? Check out, “20 Things I Wish I Could Have Told My Newly Separated Self”

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    Divorced Girl Smiling welcome video
    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

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