Dating after Divorce: 7 Tips, Trends and Red Flags to Watch For
Dating after divorce is a whole new world—one full of swipe-right surprises.
After a year of binge-watching Sex and the City and savoring the sweet silence of no one else's snoring, I started to crave the company of a man. I missed the strength of his hands, the scent of his neck, and the giddiness of exploring something exciting and new.
It was time to give dating a try. Enter Match.com.
My first match was a guy named Chad. A handsome 40-something with a killer smile and a muscular build. He owned an auto shop and lived two hours away. A bit far, but not a dealbreaker. We had some good banter going in our text thread…until the subject of kids came up.
Him: Don’t freak out.
Me: Uh… okayyy…
Him: I have 12 kids.
Me: **12** kids?!
Him: Don’t worry—I get along with their mothers.
Me: Ummm…How many mothers are we talking about here?
The usual gray text bubble flickered in and out before he finally answered.
Him: … Eight.
Is there a “clutch my pearls” emoji?
Eight mothers, twelve kids, and one man? Chad was a whole Jerry Springer show just waiting to happen.
What kind of man risks pregnancy that many times with that many women? Giant. Red. Flag.
And what kind of women are still giving the Chads of the world a chance?
I like sharing this dating story with my divorce mentees for a few reasons. One, every word of it is true. And two, there are plenty of Chads out there. They’re counting on some lonely woman to fall for a cute face and a hot body that comes with the bragging rights of a business owner. Chads know there are women who are willing to overlook the drama of 12 kids and eight mothers just to get some attention.
So what did I do? I thumbed through my other matches only to discover more Chads in queue. I canceled my Match subscription faster than you can say “dealbreaker” and moved to another app, hoping to find someone who shared my values—and my fear of STDs.
For any 40-something woman navigating the dating world after divorce, let me save you some time and frustration. Dating is completely different now. Gone are the days when a guy would walk up to a woman to start a conversation or ask her out. The dating world is mostly online. Here are a few lessons I’ve learned about the modern dating landscape:
Dating is a game of odds: To increase your chances of meeting someone worth your time, you’ve got to be intentional about the apps you’re on and even more selective about the people you spend time with.
Work on your proximity to like-minded people: Expand your circle by letting trusted friends play matchmaker or by upgrading to premium dating apps like Elite Singles.
Start with Fun, Not Your Soulmate: Forget chasing "the one"—that fairy tale is overrated. Focus on enjoying the ride, sharing laughs, and collecting gut busting stories.
Only Date Someone with Something to Lose: If a man has nothing to lose, he probably has nothing to offer. Go for someone who values what they’ve built—family, career, integrity—because you deserve more than a handsome face and empty promises.
Trust and Verify on Social Media: Once upon a time, I met a guy who proudly declared he was a medic. Sexy, right? After 30 seconds of LinkedIn sleuthing, I discovered his "medic" job was actually patient transportation—aka walking ER patients to their rooms after check-in. Moral of the story? Always fact-check, because “creative job titles” are more common than you think.
If Someone Wants to Ghost You, Let Them: Ghosting is frustrating, maybe even a little hurtful, but it also provides clarity. Anyone who can’t respect you enough to communicate isn’t worth your time or energy.
Laugh It Off and Have Fun: Dating is unpredictable, and sometimes all you can do is laugh. Awkward first dates, cringe-worthy profiles, or bad pickup lines? Chalk it up as a good story and move on.
By the time we hit our 40s, we’ve survived heartbreaks, career chaos, and maybe even raising tiny humans. We’ve earned our stripes and come out stronger—and hopefully a little smarter.
So be kind to yourself by being patient. Don’t settle for crumbs. The right guy will see your value without you having to lower your standards.