How to Date Like a Boss After Divorce (and Not Get Played)

So, you finally did it. You signed the divorce papers, cried into your wine, bought some overpriced skincare, and binged an embarrassing amount of Bravo. The long-awaited freedom is finally here! You’re freshly single and thinking, “Hey, this could be fun. I’ll just throw myself back out there. How hard could it be?”

Well, grab a drink and buckle up, sweetheart. Because the dating world you once knew has been bulldozed, rebuilt, and now operates entirely through apps filled with men named “Mike” who claim they’re “emotionally available” but still text their ex-wife when they’re drunk. Charming, right?

Back in the day, you’d grab your girlfriends, hit the local bar, and commiserate like it was an episode of Sex and the City. But now? You’re swiping on men holding fish. It’s a different battlefield, and you need armor.

Rule #1: Married Friends Are Useless

You’ll quickly learn that your married friends are sweet but clueless. They’ll offer gems like, “Just be yourself,” “Love will find you!” or my personal favorite — “Maybe lower your standards” — which is hilarious coming from someone who hasn’t dated since AOL chatrooms were still a thing.

So you’ll end up bonding with other single women, most of whom have dating horror stories that make true crime podcasts sound tame.

Listen politely. Nod empathetically. But remember: their disasters are not your destiny.

Rule #2: Negative Nancy Advice? Trash It.

When I re-entered the dating pool in my mid-forties, I made a vow: I wasn’t going to let anyone’s bitterness become my outlook. Let me tell ya, every woman will say online dating is awful. I’m here to tell you it wasn’t at all! Perhaps I had no expectations going in; therefore you can’t be disappointed.

I decided to approach every date as an experience and most of the time it was a “nice to meet you” and move on but I still enjoyed their company and had a decent time. Yes I have had a couple of weird experiences to say the least, but I just thought “I can’t wait to tell my friends this doozy!” I refused to listen to the doom-and-gloomers.

Rule #3: Decode Their BS

Let’s get real — every guy on a dating app says he’s “looking for something long-term.” Spoiler alert: they’re not. They just know that’s what women want to hear. It’s the male equivalent of “I love hiking” when they mean “I went outside once in 2018. Don’t swoon. Don’t believe. Just verify with actions.

Rule #4: Ask the Divorce Question — Then Run

Always ask if he’s divorced. Not “separated.” Not “basically divorced.” Not “we’re just living together until the lease ends.” If he’s been officially divorced for less than a year, he’s not ready — he’s a walking emotional clearance rack.

Get specific: ask the date, the year, the season — hell, ask for the judge’s name if you have to. If he’s vague, it’s because he’s lying or delusional. Either way, you don’t need that drama.

Rule #5: Nude Pics? Don’t Be That Girl

Under no circumstances should you send nude photos. Ever. He will not treasure them. He will not keep them to himself. He will absolutely add them to his phone’s Greatest Hits folder.

If a man asks for nudes before he’s even bought you a drink? Block. Delete. Light sage. Move on.

Rule #6: Meet Fast or Don’t Bother

Do not — I repeat, do not — spend weeks texting like a teenager in 2004. Two weeks max. If he’s not making a move to meet you in person by then, he’s either emotionally unavailable or married. Possibly both.

People can sound dreamy over text and be a complete dumpster fire in person. Chemistry is either there or it isn’t, and you’ll know within 10 seconds. I can’t tell you how many times it seemed like this was the perfect guy and once you meet him its just not there. Trust your gut — and your gag reflex.

Rule #7: Coffee/Cocktail, Not Candlelight

Your first meet-up should be low stakes: coffee, maybe a cocktail and a shared app. No dinner, no three-hour commitments, no soul-baring conversations about childhood trauma. Save that for later — if there is a later.

Rule #8: Got Kids? Ask the Schedule

If he has young kids, find out the custody situation. Not because kids are bad, but because they require time, energy, and emotional bandwidth — which means less of all that for you. And if he’s juggling soccer practice, a demanding job, and his CrossFit addiction? He’s not ready to prioritize you. Next.

Rule #9: Living Situation = Red Flag Alert

Ask where he lives and who he lives with. Roommates? Parents? Still crashing with the ex? These are not just logistical facts — they’re character assessments. A grown man with three roommates and no plan is not a romantic mystery. He’s a warning sign

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Rule #10: Serial Texters Are Emotional Tapeworms

Watch out for the “good morning”/“how’s your day”/“good night” guys who never make plans. These men just want to keep you orbiting their ego like a sad little moon. Do not be someone’s emotional support flirt.

Final Thoughts: No Expectations. No Apologies

You’ll kiss some frogs. You’ll waste a night or two on a man who still thinks Ed Hardy is a flex. That’s okay. Learn, laugh, and block.

The key is to stop taking it personally. It’s not about you. It’s about them being disasters. So keep your head high, your standards higher, and swipe like a woman who knows her worth — because you do.