Dating After Divorce: A Field Guide to the Men You’ll Encounter

Dating can be a wild adventure—part rom-com, part true crime podcast, and part existential crisis. And while the ultimate goal might be to meet someone amazing, let’s be honest: the dating pool isn’t exactly overflowing with Prince Charmings.

Sure, you might remember what dating was like before your marriage, but the men you meet after divorce are like navigating a foreign country—you’re never quite sure what the customs are, and sometimes you don’t even speak the same language. Among them, you’ll find a colorful assortment of characters, some good, some not-so-good, and a few downright perplexing.

You’re not the same person you were twenty years ago. Divorce has a way of teaching you what you value, what you’ll tolerate, and, most importantly, what you won’t. That growth gives you a fresh perspective on dating—and a unique ability to spot the gems in a sea of questionable contenders.

But before you dive back into the dating pool, take some time to reconnect with yourself. Dating isn’t just about finding “the one”—it’s about rediscovering who you are and what you want. Our Who Am I Now? The Essential Journal Kit for Divorced Women is the perfect place to start. It’s designed to help you explore who you are post-divorce, get clear on your values, and approach dating with confidence.

So treat dating like an experiment—a way to explore your wants, needs, likes, and dislikes. Instead of hunting for a lifelong partner right out of the gate, focus on having fun, staying curious, and learning the dating ropes again.

Because before you can find someone who’s a good fit for your life, you’ve got to reconnect with yourself. And who knows? You might just have some laughs along the way—especially when you meet some of the characters below.

The Good Guy

If you’re lucky enough to meet him, you’ll know. This guy is the unicorn of the dating world—thoughtful, funny, respectful, and emotionally available. He doesn’t play games, ghost you, or show up 30 minutes late for your first date without so much as an apology.

Meeting a Good Guy might seem rare, but building healthy, fulfilling relationships starts with understanding what you need and deserve. Check out our ReBuilding Relationships After Divorce workbook to help you navigate this new chapter.

How You Can Recognize Him:

• He actually listens: You mention your favorite book, and on the next date, he brings it up—or better yet, he’s already started reading it.
• He makes an effort: Whether it’s picking a nice restaurant or texting to see how your big presentation went, he’s not just here to check a box.
• He respects your boundaries: He’s genuinely interested in what makes you comfortable, whether it’s how much you want to share or how slow you want to take things.
• He has his act together: This doesn’t mean he’s rolling in cash or has a six-pack (though, hey, bonus points), but he has a steady job, healthy relationships, and a sense of self.

Why He’s So Rare:

Unfortunately, the Good Guy is often already taken—or recovering from his last relationship. But don’t lose hope! They’re out there, even if you have to wade through a sea of lesser options first.

​​Sure, you might encounter The Good Guy, that rare, mythical creature who actually gets it—but let’s not get ahead of ourselves.

What’s much more likely? That you’ll end up swiping right on one of these guys instead...

The Talk-Show Host

Ladies and gentlemen, meet The Talk-Show Host—a man who truly believes the world is dying to hear his life story. Got a problem? He’s got a story about the time he had that problem (and how he solved it, obviously). Want to share a cute anecdote about your dog? Good luck, because he’s already pivoted to a 15-minute monologue about the Great Dane he owned in 1997.

How You Can Recognize Him:

• He’s allergic to questions: He’ll talk at length about his work, hobbies, and childhood traumas, but when it’s your turn? Crickets.
• His go-to phrase is ‘Enough about me, let’s talk about me’: Every topic somehow circles back to his achievements, opinions, or theories on life.
• You feel like an audience member, not a date: By the end of the evening, you’ve nodded so much your neck hurts, and your margarita has gone untouched.
• His ‘listening face’ is suspiciously blank: He might be smiling and nodding, but you can tell he’s just waiting for his next chance to jump in.

How to Handle Him:

If you’re in the mood for a one-woman masterclass on the art of polite disengagement, stick it out. Otherwise, you’ve got options:

• The Subtle Redirect: Start dropping random, unrelated facts and see if he notices. Spoiler: he won’t.
• The Hard Pass: Mid-monologue, excuse yourself to the restroom and just… don’t come back.

Feeling stuck on how to steer the conversation back to yourself? Our First Date Conversation Guide has tips to help you navigate tricky first-date dynamics with ease.

Why He’s Everywhere:

Let’s face it—this guy thrives in the wild, untamed lands of online dating. His profile probably boasts “great conversationalist,” which, unfortunately for you, is code for “I love the sound of my own voice.” 

Mr. Mirror Mirror

This guy’s biggest competition for your attention is… himself. He’s more invested in his reflection than he could ever be in a relationship. It’s great that he takes pride in his appearance, but take note if it’s at the exclusion of everything else.

How You Can Recognize Him:

• Selfie overload: He’s constantly checking himself in mirrors, windows, or even his spoon at dinner.
• Gym talk galore: The conversation inevitably circles back to his workout regimen, protein shakes, or the time he almost became a personal trainer.
• Skincare aficionado: His bathroom counter looks like a Sephora pop-up shop.
• Compliments are a one-way street: You might look stunning, but don’t expect him to notice—unless your outfit reflects well in his Instagram photo.

How to Handle Him:

Unless you’re equally into his biceps, this one’s best left to his followers. A polite smile and an exit strategy will do the trick.

The Relationship Sprinter

This guy moves fast—really fast. He’s mentally moved you into his apartment, named your future children, and invited you to Thanksgiving with his family… all before you’ve ordered dessert.

How You Can Recognize Him:

• Overwhelming affection: He’s texting good morning and goodnight by day two, and by day four, he’s calling you “babe.”
• Future talk overload: He drops hints about marriage, joint bank accounts, and “someday when we...”
• Too much, too soon: Flowers, gifts, and declarations of love appear out of nowhere, leaving you wondering if you missed a few steps.
• Attachment vibes: He mentions he’s “just looking for someone to settle down with” approximately every 10 minutes.

How to Handle Him:

• Pump the brakes: If you like him, let him know you need to slow things down. If he can’t, well… that’s a red flag in itself.
• Be kind, but firm: He’s not a bad guy—just a little overeager. Let him know you’re looking for a marathon, not a sprint. 

The Emotional Backpacker

He’s got baggage—a lot of it—and unfortunately, he’s looking for someone to help him carry it. On the surface, he seems sensitive and introspective, but scratch a little deeper, and it’s clear he’s still living in the shadow of his ex (or exes).

How You Can Recognize Him:

• Ex talk overload: He’s “not over her,” “still processing,” or “learning to trust again.” You’ll feel like you’re on a date with him and his past relationships.
• Emotional word vomit: He dives into deep, heavy topics way too soon, leaving you to wonder if he thinks this is couples’ therapy.
• Unhealed vibes: Whether it’s bitterness, regret, or just plain sadness, his emotional state feels like a ticking time bomb.
• Oversharing central: You’ll know more about his last relationship than his hobbies or favorite pizza topping.

How to Handle Him:

• Set boundaries: Gently steer the conversation back to lighter topics, but don’t feel obligated to play emotional support.
• Be upfront: If his baggage feels like too much, kindly let him know you’re not in a place to take it on.

Why He’s So Common:

Breakups are hard, and some people dive into dating as a distraction instead of taking time to heal. It’s not your job to fix him—but maybe wish him luck on his journey.

Mr. Swipe-and-Go

This guy’s intentions are clear from the start: he’s here for a good time, not a long time. Subtlety is not his strong suit, and if he had a motto, it would be “straight to the point.”

How You Can Recognize Him:

• Late-night texts: If he texts you “U up?” at 11:37 p.m., he’s not looking for a deep connection.
• Minimal effort: His first date suggestion is meeting “somewhere casual” - by which he means his place.
• Fast-paced flirting: He doesn’t waste time with small talk; he’s all about compliments, winks, and… well, you get the idea.
• Inconsistent communication: He disappears for days and resurfaces only when he’s bored.

How to Handle Him:

• Know your boundaries: If you’re on the same page, that’s cool, go for it. If not, don’t feel pressured to play along.
• Swipe left in real life: Politely let him know you’re looking for more. And if he can’t take the hint? Block and delete.

Why He’s Everywhere:

Modern dating apps make it easy for guys like this to thrive. But don’t worry—once you spot the signs, he’s easy to avoid.

Not sure where your boundaries lie? Our Dealbreakers Before Dating workbook helps you define what you want—and don’t want—before saying yes to that first date.

The Wandering Philosopher

Ah, the deep thinker. He’s full of existential questions, quotes from obscure poets, and musings about the meaning of life. At first, his intellectual side might seem intriguing—but after a while, you’ll start to wonder if he’s just stalling to avoid sharing anything real about himself.

How You Can Recognize Him:

• Heavy conversation from the get-go: Before your appetizer arrives, he’s already asked you, “But what is love, really?”
• Endless hypotheticals: He thrives on “What if” scenarios, but don’t expect him to commit to actual plans for next weekend.
• Obsessed with abstract ideas: He’ll happily discuss the universe, destiny, and time travel but struggles to answer simple questions like, “Where do you work?”
• Overuses quotes: Whether it’s Rumi, Nietzsche, or an indie band you’ve never heard of, he always has a quote to back up his point.

How to Handle Him:

• Engage with caution: If you love a good philosophical debate, this might be your guy. Just don’t expect to dive into practical topics like grocery shopping or how he feels about long-term relationships.
• Test his grounding: Ask him about something simple and concrete—like his favorite comfort food. If he launches into a philosophical debate on the cultural significance of food, you’ve got your answer.

Why He’s So Common:

The Wandering Philosopher often uses deep thoughts to mask insecurity or indecision. He’s not a bad guy - just stuck in his head.

The Never-Gonna-Grow-Up Guy

Meet Peter Pan in the flesh. He’s carefree, spontaneous, and fun, but when it comes to maturity… let’s just say his emotional age stalled somewhere around 22.

How You Can Recognize Him:

• Lifestyle red flags: He’s still renting that “bachelor pad” he’s had for years, complete with mismatched furniture and a dusty drum set in the corner that hasn’t been touched since 2012.
• Job situation: He has one… sort of. Maybe he’s “consulting” or working on a “passion project” that’s been in the works for a decade. Stability isn’t his strong suit.
• Hobbies scream Midlife Crisis: Think endless weekends of fantasy football, buying expensive gadgets he never uses, or spending hours researching his dream motorcycle instead of, you know, life responsibilities.
• Avoids responsibility: Commitment? He laughs it off. His idea of planning is figuring out what to order for takeout. Don’t even think about bringing up retirement savings.

How to Handle Him:

• Enjoy the ride, if you’re into it: He’s fun in small doses, but if you’re looking for a long-term partner, he’s not your guy.
• Set boundaries: Don’t let his laid-back vibe convince you to lower your standards.

Why He’s Everywhere:

Some men just love the carefree life and aren’t ready to grow up—and that’s okay! Just make sure you’re not wasting your time if you’re looking for something serious.

The Mystery Man

He’s charming, enigmatic, and keeps you intrigued… but only up to a point. The problem? He’s a little too mysterious. You know almost nothing about him, and he’s definitely not in a rush to share more.

How You Can Recognize Him:

• Dodges personal questions: Ask him where he works, and he’ll say something vague like “finance” and quickly change the subject.
• Elusive social media presence: He’s either off the grid or keeps his accounts locked down tighter than a celebrity breakup.
• Unpredictable communication: Sometimes, he’s attentive and engaged; other times, he vanishes for days without a word.
• Refuses to define the relationship: He’s fine keeping things casual, but any mention of labels makes him bolt.

How to Handle Him:

• Trust your gut: If his behavior feels shady, don’t ignore the red flags.
• Ask direct questions: If he can’t—or won’t—give you straight answers, it might be time to move on.

Why He’s Everywhere:

Some guys love the allure of being mysterious, while others just aren’t ready to be vulnerable. Either way, if he’s not opening up, he’s not worth your time.

The Checklist Guy

He’s looking for a partner… but not just any partner. He’s got a mental checklist, and he’s evaluating whether you tick all his boxes. Spoiler: it’s exhausting.

How You Can Recognize Him:

• Interview-style dates: He peppers you with questions like, “Are you planning to retire soon? How do you feel about traveling six months of the year? Are you a wine person or a beer person?”
• Overly specific criteria: He’s looking for someone who’s “cultured but not snobby,” owns a golden retriever, loves to host dinner parties, and can discuss retirement portfolios with enthusiasm.
• Lacks flexibility: If you don’t match his dream partner exactly, he’ll let you know—subtly or not-so-subtly.
• Makes you feel like a project: Instead of enjoying the date, you feel like you’re auditioning for a role in his life.

How to Handle Him:

• Be yourself: Don’t mold yourself to fit his checklist.
• Decide if you’re okay with it: If his criteria feel reasonable, great. If not, politely bow out and leave him to his spreadsheets.

Why He’s Everywhere:

The Checklist Guy is just trying to find someone compatible… but often at the expense of genuine connection.

Don’t let anyone make you feel like you’re auditioning for a role. Our Rooted in Worth workbook helps you embrace your value and stay true to yourself in any relationship.

The Nice Guy (But Not Really)

He seems sweet at first—polite, friendly, maybe even a little shy. But spend a little more time with him, and you’ll realize that his “nice” exterior is just a cover for bitterness, entitlement, or an unhealthy obsession with being praised for the bare minimum.

How You Can Recognize Him:

• Overly self-deprecating: He’s constantly fishing for reassurance with comments like, “Girls never go for guys like me.”
• Plays the victim: He’ll bring up how he’s “always finishing last” or how no one appreciates his “nice guy” qualities.
• Gets resentful when you’re not into him: If you’re not interested, his sweet persona can turn sour fast.
• Low-key manipulative: He uses guilt or pity to keep you engaged.

How to Handle Him:

• Call out bad behavior: If he starts playing the victim or trying to guilt-trip you, don’t be afraid to shut it down.
• Set clear boundaries: This guy thrives on blurred lines, so make yours crystal clear.

Why He’s Everywhere:

The Nice Guy isn’t always malicious—he’s often just insecure and unhealed. But don’t let that make you feel responsible for his feelings.

Laugh, Learn, and Keep Going

Dating can feel like running a gauntlet of personalities, quirks, and red flags. But for every Peter Pan or Talk-Show Host, there’s also the occasional Good Guy waiting to restore your faith in the process.

No matter who you meet on your dating journey, the key is staying connected to your values and goals. Whether you’re laughing at these dating archetypes or nodding in recognition, it’s important to stay grounded in your own journey. Our collection of tools—from the Dealbreakers Before Dating workbook to the ReBuilding Relationships guide—can help you navigate dating with clarity and confidence.

So laugh at the missteps, share your stories with your girlfriends, and remember: the right one will stand out for all the right reasons.