the 411

The Divorced Mom’s Dating Guide To Red Flags

And some green flags, too, for good measure.

by Penelope
The 2025 Divorce Issue

Welcome to Ask A MWLTF (yes, that’s Mother Who Likes to F*ck), a monthly anonymous advice column from Scary Mommy. Here we’ll dissect all your burning questions about motherhood, sex, romance, intimacy, and friendship, with the help of our columnist, Penelope, a writer and mental health practitioner in training. She’ll dish out her most sound advice for parents on the delicate dance of raising kids without sacrificing other important relationships. Email her at askpenelope@scarymommy.com.

Q: I’m newly divorced, finally feeling like myself again, and thinking about dating. Finding someone to have fun and sex with sounds nice, but not worth my sanity or independence. Also, it’s been a decade since I made out with a person who hadn’t also watched me clip my toe nails or use the toilet. Dating, much less internet dating, seems terrifying. How do I begin to tell who’s worth meeting and who’s going to drain my soul, my wallet, or ask me to do his laundry on the second date? Help. — Terrified but Hopeful

Dear Terrified but Hopeful,

First of all, breathe. You’re alive. You got through a divorce without losing all hope in the possibility of companionate love. Also, you likely know your own needs and boundaries better than you ever have before. So fear not. Or fear not too much. That knowledge will protect you as you enter the fray. A wise woman once told me that if you’re in the right frame of mind, there are no bad dates — there are only good dates and good stories. This holds true for everyone, but perhaps most of all for the divorced and dating crowd.

That said, dating post-marriage is not for the faint of heart — especially if you’re a mom. Especially if you’ve spent years carrying the emotional load of a family while slowly disappearing inside your own life. The good news? You’re wiser now. The bad news? You’re about to meet a lot of men who aren’t. Luckily you don’t need to date all the men. You just need to get very good at spotting the red flags — the stuff that seems like a quirky personality trait at first but turns out to be your next six months of unpaid labor and emotional whiplash. For a thorough and insightful primer on that process, check out the Burned Haystack Method created by Jennie Young, a professor of applied rhetoric and gender studies who teaches women to focus on intentionality and efficiency in online dating. For a down-and-dirty, Cliff Notes version, here’s my official, Field-Tested, No-BS Guide to Red Flags When Dating After Divorce.

The Official MWLF Red Flag Checklist

1. No flagrant personality disorders.

If he lovebombs you on date two and casually mentions how “everyone turns on him eventually,” RUN.

2. No active substance abuse.

You are not here to be his rehab plan. If he refers to his dealer as “my guy,” hard pass.

3. Must not hate his job.

It’s fine to be in transition. It’s not fine to be in a rage spiral about capitalism every time you ask what he does for work.

4. Must have a job.

Yes, this includes “figuring it out.” No, crypto doesn’t count.

5. Must not hate his parents.

If he’s still fighting with his mom in his 40s, you will become the mom.

6. Must not idealize his parents.

Especially his mom. We are not dating a Norman Bates reboot.

7. Must do his own laundry.

No adult man should describe the washing machine as “confusing.”

8. Must be able to cook at a basic, survivalist level.

Three meals that aren’t toast or takeout. That’s it. That’s the bar.

9. No weird food aversions.

Refusing to eat anything green after age seven is not a personality. It’s a vitamin deficiency.

10. Must have a few things on the walls.

If his apartment looks like a hostage situation, it probably is (emotionally).

11. Must own books.

At least a couple. They don’t all have to be about stoicism.

12. Must have a child or a pet (preferably a pet).

Proof of sustained care for another living being is non-negotiable.

13. If divorced, must be able to say why.

If the explanation is, “My wife went crazy,” that’s your cue to walk out mid-salad.

14. Must not expect you to explain why his wife ‘went crazy.’

You’re not his therapist. You’re not his wife. You’re not his mom. Act accordingly.

15. Must not be in a rush to remarry.

If he proposes on date three, he’s not looking for love—he’s looking for a project manager.

16. Must not be looking for an unpaid therapist.

If he says “you’re such a good listener” before he asks you a single question about your life, abort mission.

Needless to say, this list eliminates about 99% of men on the internet. And thank God. Because post-divorce dating isn’t about lowering your standards — it’s about raising them to match the version of yourself you fought to become.

You already know what it’s like to give too much, compromise too often, and feel too alone inside a relationship. You’re not doing that again.

But don’t worry — it’s not all red flags and walking cautionary tales. There are good ones out there. In fact, here’s your cheat sheet for what to say yes to.

MWLF-Approved Green Flags

He texts back without being weird about it.

He knows what IUD stands for.

He refers to therapy as something he does, not something he tried once because of a breakup in 2016.

He asks questions and actually listens to the answers.

He has friends. Real ones. Not just guys he plays poker with once a year.

He owns a vacuum and knows how to use it.

He doesn’t call his ex “crazy,” even if it ended badly.

He thinks emotional maturity is sexy.

He’s kind to waitstaff, animals, and children — especially ones that aren’t his.

He doesn’t expect you to be grateful he’s “okay with dating a single mom.”

In sum, dating after divorce doesn’t have to be a horror show. But it does require you to know your limits, trust your gut, and not waste your precious, hard-earned peace on anyone who makes you feel small.

You’re not starting over — you’re starting wiser. Trust that. And when in doubt? Red flag it, and keep walking.