Dating should add to your life, not drain it. But so many smart, strong women (and men) find themselves stuck giving time and energy to someone who isn’t right for them. Recognizing the signs early can save your heart, mental health, and years of effort. Some red flags are obvious, while others are subtle, showing up as quiet aches or little disappointments. This list cuts through the confusion to help you see when it’s time to walk away.
We’ve all been there, holding onto someone who just isn’t right, hoping things will change. But deep down, you know when it’s time to stop second-guessing and start listening to your gut. A relationship should be a source of joy and growth, not confusion and self-doubt. If you’re noticing more red flags than real connection, it might be time to take a step back and evaluate. Here are the 15 clearest signs you’re investing your time in Mr. or Ms. Wrong.
1. Lack of Consistent Communication
If reaching them feels like a guessing game, interest is likely low. You’re left waiting for texts that never come, or when they finally reply, it’s short and dismissive. You find you’re always the one to keep things going, without real effort on their part. Experts agree that connection is consistent and intentional. If it’s not, it’s time to pause and ask why.
Watch for:
- Sporadic messages, especially when you need them most
- Long silences, only to reappear like nothing happened
- Never initiating conversations or plans
2. You Feel Drained After Interactions
Spending time together shouldn’t wear you out.
Normal tiredness is different from the heavy, anxious feeling that lingers after another difficult chat. If you breathe easier when they leave, emotional balance is missing. Experts agree that love should lift you up, not weigh you down.
3. They Avoid Introducing You to Friends or Family
You don’t know anyone important in their life. They dodge invites or make vague promises.
Meeting loved ones builds deeper trust. Avoidance here keeps you at arm’s length. Real connection is about integration, not isolation.
4. You’re Always the One Initiating Plans
If you stopped texting, calls, and plans would dry up. You’re the event planner and motivator, while they coast. Keeping a little log of who makes the first move week after week can reveal the pattern. Remember, healthy relationships have balance; it shouldn’t feel one-sided.
Checklist:
- Who texted first last time?
- Who chose the place to meet?
- Who followed through on plans?
5. Lack of Respect for Your Time
Late again? Canceled at the last minute?
You begin to expect disappointment. Regular disrespect for your schedule shows low regard and keeps you on the back foot. Experts agree that respect is non-negotiable; your time is just as valuable as theirs.
6. They Don’t Make an Effort to Understand You
When you talk about your dreams, values, or even your day, the interest isn’t there. They forget what matters to you and brush aside your feelings.
Relationships thrive on curiosity and care. If they’re not interested in understanding you, they’re not invested.
7. You Feel More Anxious Than Happy
You walk on eggshells, unsure if today will be another letdown. Excitement has been replaced by knots in your stomach. Happiness should come easily, not be squeezed out by worry.
Experts agree that peace over pressure is key—if you’re more tense than joyful, it’s a sign.
8. They’re Secretive or Hide Important Details
You know nothing about their schedule, their past, or even basic facts friends already share.
They change the subject or feed you half-truths, leaving you uneasy. Authentic love doesn’t hide; it shows up fully.
9. You Constantly Make Excuses for Their Behavior
You defend them to your friends, explaining away lateness, silence, or rudeness.
You rewrite the script to make them look better and silence your own doubts. Experts agree that accountability matters—if you’re the only one justifying, it’s time to rethink.
10. Their Actions Don’t Match Their Words
They talk big, but follow-through is a joke. Grand promises drop flat.
Words and actions should line up. If not, trust unravels. Experts agree that consistency is key.
11. You Feel Lonely Even When You’re Together
The silence between you feels louder than any argument.
Even seated side-by-side, you feel alone. Companionship without connection is just sharing space. Real love fills the room with presence and partnership.
12. They Don’t Prioritize You During Important Moments
You celebrate alone, cry alone, and face big days solo.
Birthdays, job milestones, and tough times pass without their presence or effort. Experts agree that prioritization is an act of love, and you deserve to feel seen.
13. You’re Hiding Parts of Yourself Around Them
You bite your tongue or downplay your quirks, afraid you’ll push them away.
Authenticity fades, and you lose pieces of yourself trying to keep peace. Experts agree that you should always feel safe to be yourself.
14. They Seem Indifferent to Your Needs
Your needs—emotional, physical, or mental—get dismissed or ignored.
You feel invisible or burdensome for asking for basic care. True connection is about meeting each other where you are.
15. You Feel Relief or Happiness When You’re Apart
When they leave, you breathe easier. You’re lighter, happier, and more like yourself without them.
If you’d rather be alone than together, that’s your intuition speaking. Listen, because your heart already knows what your mind is resisting.
Remember
The right person will add to your life, not subtract from it. Experts agree that real love makes the everyday feel extraordinary. If you’re not getting that, it’s time to step back and ask yourself what you really deserve.
The Texting Trap: Why Too Much Texting Can Ruin Your First Date
The way we communicate has completely transformed, especially when it comes to dating. Texting is quick, easy, and feels low-risk, but could it actually be sabotaging your first dates before you even meet?
If you’ve ever found yourself in an awkward silence after days of non-stop texting, you’re not alone. We call this the Texting Trap, a cycle of endless messaging that creates false intimacy and burns out the excitement before the real date even happens.
Let’s unpack the ways over-texting could be killing your first-date potential and how to change that for good.
1. Too Much Texting Kills the Mystery
First dates thrive on curiosity and discovery. But if you’ve already exchanged every favorite movie, breakfast choice, and pet peeve over text, there’s little left to uncover when you finally meet.
The magic of a first date is in the unknown, those fresh questions that spark real-time reactions. When texting turns into a full-blown autobiography, that anticipation fades. Keep some of your stories for the date to keep the energy fresh and engaging.
2. Miscommunication Is Practically Guaranteed
Without tone, facial expressions, or body language, texts can easily be misinterpreted. A sarcastic joke might come off as harsh. A delay in response could be read as disinterest.
These micro-misunderstandings pile up, setting the wrong tone before you even meet. Saving the deeper conversations for in-person interactions allows for clarity and connection.
3. Texting Builds False Expectations
Let’s be honest: texting lets us curate our responses. We can pause, think, and craft the perfect reply, but that’s not how real conversations work.
The person you’ve been texting for days might seem sharp and charming through their carefully chosen words, but in real life, that chemistry might not translate.
First dates should be about real-time connection, not trying to match the polished versions of ourselves we’ve been texting.
4. Emotional Intimacy Develops Too Fast
It’s easy to share personal stories over text because it feels less vulnerable. But that rapid connection can lead to unrealistic expectations before you’ve even shared a meal together.
Emotional intimacy needs the balance of face-to-face interaction to really take root. Otherwise, it can feel like you’re on a third date emotionally when it’s actually your first in person.
5. Over-Texting Leads to Burnout Before You Even Meet
Conversations should be building excitement, not draining it.
If you’ve been texting nonstop for days or weeks, that first date can feel more like a formality than an adventure. Keep the pre-date texting light and focused on logistics to avoid burnout.
6. It Steals the Build-Up of Anticipation
Anticipation is half the fun of dating. When you’ve already spilled everything over text, there’s no room left for those fun ‘getting to know you’ moments.
Keep some stories for when you’re face-to-face, it’ll make the experience feel more authentic and exciting.
7. Texting Stays Surface-Level
While it’s great for quick check-ins and flirty banter, texting rarely dives deep.
Real conversations, the ones that build lasting connections, happen face-to-face. Save those more meaningful discussions for when you’re together.
8. You Miss the Chance to Gauge Real Chemistry
Chemistry isn’t something you can feel through a screen.
That spark, that laugh, that body language, you only get those signals in person. If you’re spending too much time in the texting phase, you might be missing the real-world connection entirely.
9. It Makes You Overthink Everything
The more you text, the more room there is for second-guessing.
Did they like that joke? Was that emoji too much? Did I reply too quickly? By the time you meet, you might already feel drained from all the mental gymnastics.
Breaking Free from the Texting Trap
Texting is great for setting up dates and sharing quick thoughts, but it’s not a substitute for real-world connection.
The key is to text with purpose, not out of habit. Keep your texts light and focused on making plans, not spilling your life story. When you do finally meet, you’ll find there’s so much more to discover, and that’s where the real magic happens.
If you’re tired of texting games and fairy tale expectations, it’s time for a fresh approach. Grab a copy of F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story and learn how to create a real connection, without the burnout.
Get the book on Amazon and start writing your own love story today.
5 Steps to Start Dating Again After a Breakup
Getting back into the dating game after a breakup, divorce, or just a long pause can feel like learning to walk in heels again—awkward, unsteady, and honestly, a little terrifying. It’s natural to wonder: What if it’s different now? What if it’s too soon?
It is different now. But that doesn’t mean it’s not possible.
Whether it’s in the late 20s, 30s, or 40s, stepping back into dating isn’t about chasing some perfect outcome. It’s about reconnecting with what matters and creating space for something new. It doesn’t have to drain energy or self-worth.
Here’s how to ease back in without burning out:
1. Give Yourself Permission to Start Slow
There’s no need to rush. Sometimes, a soft launch back into the dating world is exactly what’s needed. That might look like updating a profile and then ignoring the apps for a week. Or just having a conversation with someone new—no pressure attached.
Check in regularly. Is there curiosity, or does it still feel like too much? That answer will guide the pace, and that pace is perfect.
Starting slow isn’t about hesitation; it’s about self-awareness. If the nervous system still feels frazzled at the idea of swiping, that’s a sign to go easy. Dip a toe in, observe how it feels, and step back out if necessary. Intentional dating is sustainable dating.
2. Get Clear on Boundaries and Needs
This time, dating isn’t happening on autopilot. It’s about intention.
Consider: What is available now? What is no longer acceptable? Whether it’s connection, companionship, or something more serious, clarity is everything.
Write down non-negotiables. Keep them accessible as reminders. These aren’t walls; they’re guardrails. They help maintain alignment with values, even when chemistry is strong.
If a reminder is needed: Boundaries are bridges to authentic connection, not barriers to love.
3. Try Just One New Way to Meet People
There’s no need to sign up for every app, agree to every setup, or spend Saturdays speed dating unless that’s genuinely exciting. Choose one way to dip a toe back in.
Maybe it’s attending a local mixer, trying a single dating app, or saying yes to that invite from a social circle. The goal here is simple: show up. Not to impress—just to connect.
No pressure. No performance. Just presence.
4. Watch the Inner Dialogue—Before and After Dates
This one’s big because the way thoughts are framed shapes the entire experience.
If thoughts like “It’s too late for this” or “No one decent is out there” pop up, it’s time to pause and reframe. Try: “Showing up fully.” Or “Every interaction teaches something new.”
Inner dialogue can either fuel energy or drain it. Choose wisely.
5. Celebrate the Small Wins
Not every date will lead to butterflies or a second meeting, and that’s perfectly fine. Progress isn’t always flashy. Sometimes, it looks like:
These are wins. Celebrate them. Progress in dating, like in anything else, is built one small, courageous act at a time.
Final Thought: Start Where You Are
Dating again isn’t about being ready in some mythical, fully healed way. It’s about being willing—willing to try, to learn, to stay curious.
There’s no need to be fearless. Just be present.
Take a deep breath. Set the pace. Keep boundaries firm. Speak with kindness internally. And celebrate every single step taken back toward love.
Because it’s not starting over—it’s starting from experience.
Ready to step back into dating with confidence?
Start with a profile that truly reflects you. Our Profile Starter Kit gives you plug‑and‑play templates, storytelling prompts, and a bonus photo‑selection video so your profile feels real, energetic, and aligned with who you are now.
Get the Profile Starter Kit and make your next swipe a match on your terms.
How to Avoid Love-Bombing Heartbreak
What is Love-Bombing?
Love-bombing is when someone overwhelms you with excessive attention, flattery, and gifts in the early stages of dating. They text constantly, want to see you all the time, and make grand declarations that feel like you’ve stepped into a rom-com. But like any good movie, it’s scripted, and the ending is rarely a happy one.
At its core, Love-Bombing is about control. It’s designed to create dependency by making you feel like you’ve found “the one” almost instantly. But real love is built over time; it’s a slow burn, not a flash in the pan. If the connection feels too good to be true right out of the gate, it might be.
Why Does It Feel So Good at First?
The initial rush of a love bomber’s attention is intoxicating. The constant texts, surprise gifts, and over-the-top compliments tap right into our brain’s reward system. That’s because all that attention floods your system with dopamine, making you feel euphoric. It’s like a fireworks display, brilliant, intense, and impossible to ignore.
But here’s the catch: fireworks fade, and so does the intensity of Love-Bombing. Once the emotional hook is set, love bombers often start to pull back, leaving you confused and craving that initial high. It’s emotional whiplash, and it’s designed to keep you chasing that first rush.
Neurologically, love-bombing hits like a new crush on steroids. All that attention floods your brain with dopamine—the “feel good” chemical—and oxytocin, the one that makes you want to bond fast. That combo lights up your brain’s reward center like a pinball machine. It feels amazing… and addictive. But just like any high, what goes up usually comes crashing down.
How to Spot Love-Bombing Early
To protect yourself from Love-Bombing, you have to know what to look for. Here are some major signs:
If you notice these patterns, it’s time to slow things down. True connection takes time to grow, and anyone worth building with will respect your pace.
How to Protect Yourself
The Bottom Line
Love-bombing might feel like a fireworks show—dazzling at first, but over in a flash.
If you’ve been a victim of love-bombing, it’s not your fault! Most people who do this are masters of manipulation and have done it so many times they’re completely cut off from the emotional consequences that you’re suffering through.
While we cannot change someone else’s behavior, we can do our best to protect ourselves, communicate clearly, and spot the signs of love-bombing before they break our hearts. True love is possible for you if you believe you deserve someone who shows up for you fully and you’re patient enough to let it unfold.
Still wondering how to spot love-bombing early?
In the Dates & Mates podcast episode “2025 Love Astrology & Lovebombing Bombshell,” we answer a listener’s question about what to do when someone showers you with affection on a dating app… only to vanish. We break down the signs, explain why it happened, and share real strategies to stay open without getting played.
Listen now and learn how to protect your heart and your hope.
Michelle Obama & Craig Robinson Communication Q&A Minisode
Have you ever felt like staying in touch has become harder than ever, even with all the tech tools at our fingertips? If you’ve ever found yourself stuck in a texting loop or missing the sound of someone’s voice, you’re not alone.
This week’s Dates & Mates Minisode features two powerhouse voices on connection: former First Lady Michelle Obama and her brother Craig Robinson, co-hosts of the hit IMO Podcast. They’re getting candid about the real ways they stay connected to those they love—and what that looks like in a world of texts, FaceTimes, and digital overwhelm.
(1:25) Meet the IMO Hosts
Michelle and Craig are more than just siblings—they’re thoughtful communicators with powerful insights on how to stay close across distance, generations, and even communication styles.
In this episode, they reveal how their personal approaches to staying in touch reflect deeper shifts in how we all relate today.
(6:44) Texts vs. Phone Calls
This segment highlights Michelle and Craig’s different approaches to one of the biggest modern communication dilemmas.
Craig prefers texts for their simplicity and efficiency, while Michelle uses them to check in on her kids in a way that’s quick but still personal.
As Michelle puts it, “I know you have your phone, so when I text you, text me back. All I’m trying to do is make sure that you’re alive.”
(11:18) Planning for Spontaneity
Instead of overloading our calendars with set calls, Michelle and Craig explore how to build more flexibility into our communication habits.
The conversation opens up ideas around creating windows of availability rather than rigid appointments, helping us stay connected without the pressure.
(15:37) Zoom Isn’t Just for Work
Some of the digital habits we formed out of necessity have proven to be surprisingly valuable.
Michelle and Craig discuss how their family embraced tools like Zoom and FaceTime, not just during lockdowns, but as lasting practices to maintain closeness across distance.
If you’ve ever felt like tech has taken the intimacy out of communication, this Minisode offers a refreshing and practical shift in perspective.
💌 Do you have questions? Damona has the answers!
Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!
Access Daily: Valentine’s Day & World Dump Day
Dating with Damona: Access Daily hosts Mario and Kit got the scoop on Valentine’s Day and World Dump Day (yes, that’s a real thing!) with Damona.
From discussing the art of the perfect breakup to exploring new dating terms like “pebbling” and “fine whining,” the conversation covered both the sweet and sour sides of modern romance.
Damona shared practical tips for singles considering a friend’s matchmaking offer, encouraging daters to know their “must-haves” before saying yes to a setup.
Top 15 Signs You’re Wasting Time on Mr. or Ms. Wrong
Dating should add to your life, not drain it. But so many smart, strong women (and men) find themselves stuck giving time and energy to someone who isn’t right for them. Recognizing the signs early can save your heart, mental health, and years of effort. Some red flags are obvious, while others are subtle, showing up as quiet aches or little disappointments. This list cuts through the confusion to help you see when it’s time to walk away.
We’ve all been there, holding onto someone who just isn’t right, hoping things will change. But deep down, you know when it’s time to stop second-guessing and start listening to your gut. A relationship should be a source of joy and growth, not confusion and self-doubt. If you’re noticing more red flags than real connection, it might be time to take a step back and evaluate. Here are the 15 clearest signs you’re investing your time in Mr. or Ms. Wrong.
1. Lack of Consistent Communication
If reaching them feels like a guessing game, interest is likely low. You’re left waiting for texts that never come, or when they finally reply, it’s short and dismissive. You find you’re always the one to keep things going, without real effort on their part. Experts agree that connection is consistent and intentional. If it’s not, it’s time to pause and ask why.
Watch for:
2. You Feel Drained After Interactions
Spending time together shouldn’t wear you out.
Normal tiredness is different from the heavy, anxious feeling that lingers after another difficult chat. If you breathe easier when they leave, emotional balance is missing. Experts agree that love should lift you up, not weigh you down.
3. They Avoid Introducing You to Friends or Family
You don’t know anyone important in their life. They dodge invites or make vague promises.
Meeting loved ones builds deeper trust. Avoidance here keeps you at arm’s length. Real connection is about integration, not isolation.
4. You’re Always the One Initiating Plans
If you stopped texting, calls, and plans would dry up. You’re the event planner and motivator, while they coast. Keeping a little log of who makes the first move week after week can reveal the pattern. Remember, healthy relationships have balance; it shouldn’t feel one-sided.
Checklist:
5. Lack of Respect for Your Time
Late again? Canceled at the last minute?
You begin to expect disappointment. Regular disrespect for your schedule shows low regard and keeps you on the back foot. Experts agree that respect is non-negotiable; your time is just as valuable as theirs.
6. They Don’t Make an Effort to Understand You
When you talk about your dreams, values, or even your day, the interest isn’t there. They forget what matters to you and brush aside your feelings.
Relationships thrive on curiosity and care. If they’re not interested in understanding you, they’re not invested.
7. You Feel More Anxious Than Happy
You walk on eggshells, unsure if today will be another letdown. Excitement has been replaced by knots in your stomach. Happiness should come easily, not be squeezed out by worry.
Experts agree that peace over pressure is key—if you’re more tense than joyful, it’s a sign.
8. They’re Secretive or Hide Important Details
You know nothing about their schedule, their past, or even basic facts friends already share.
They change the subject or feed you half-truths, leaving you uneasy. Authentic love doesn’t hide; it shows up fully.
9. You Constantly Make Excuses for Their Behavior
You defend them to your friends, explaining away lateness, silence, or rudeness.
You rewrite the script to make them look better and silence your own doubts. Experts agree that accountability matters—if you’re the only one justifying, it’s time to rethink.
10. Their Actions Don’t Match Their Words
They talk big, but follow-through is a joke. Grand promises drop flat.
Words and actions should line up. If not, trust unravels. Experts agree that consistency is key.
11. You Feel Lonely Even When You’re Together
The silence between you feels louder than any argument.
Even seated side-by-side, you feel alone. Companionship without connection is just sharing space. Real love fills the room with presence and partnership.
12. They Don’t Prioritize You During Important Moments
You celebrate alone, cry alone, and face big days solo.
Birthdays, job milestones, and tough times pass without their presence or effort. Experts agree that prioritization is an act of love, and you deserve to feel seen.
13. You’re Hiding Parts of Yourself Around Them
You bite your tongue or downplay your quirks, afraid you’ll push them away.
Authenticity fades, and you lose pieces of yourself trying to keep peace. Experts agree that you should always feel safe to be yourself.
14. They Seem Indifferent to Your Needs
Your needs—emotional, physical, or mental—get dismissed or ignored.
You feel invisible or burdensome for asking for basic care. True connection is about meeting each other where you are.
15. You Feel Relief or Happiness When You’re Apart
When they leave, you breathe easier. You’re lighter, happier, and more like yourself without them.
If you’d rather be alone than together, that’s your intuition speaking. Listen, because your heart already knows what your mind is resisting.
Remember
The right person will add to your life, not subtract from it. Experts agree that real love makes the everyday feel extraordinary. If you’re not getting that, it’s time to step back and ask yourself what you really deserve.
Master Class: The Texting Trap
Have you ever found yourself deep in a text thread, wondering if you’re actually building a connection or just killing time? Do you replay your replies in your head, panic when a message goes unanswered, or second-guess what that one little emoji was supposed to mean?
You’re not alone.
The truth is, modern love isn’t just emotional, it’s digital. The way we connect, flirt, and fall is shaped more than ever by the devices in our hands.
This week, we’re talking about what we call the communication crisis. How texting, DMs, and digital overload are shaping our relationships and what we can do about it.
This episode is a special solo masterclass. No guests, just sharing everything you need to know about navigating digital communication with confidence, clarity, and connection.
(2:01) Are We Losing the Plot or Learning a New Language?
We used to believe the problem was dating apps. But what we’ve realized is that it’s not the apps, it’s how we use them.
The real shift in dating today is in how we communicate. Over 65% of our romantic conversations now happen digitally. That means we can’t just wish it away, we have to learn how to do it better.
Texting, voice notes, emojis, memes, these aren’t distractions. They’re the main way we relate. And once we stop seeing digital communication as something separate from “real” dating, we can start to use it as a tool instead of a trap.
(6:41) Stuck in the Texting Trap
You match. You message. Maybe it even feels promising. But somehow… you never actually meet.
Welcome to the texting trap, where you build momentum through messages, only to have it stall out in digital limbo. It’s that false sense of intimacy that keeps us feeling like something’s happening, even when nothing’s moving forward.
The longer we stay in it, the more we start projecting and fantasizing until the real person can’t live up to the version we’ve created in our head. We walk you through the telltale signs you’re stuck and explain how to break free before your connection ghosts itself.
(20:57) Texting Like a Pro, Not a Pen Pal
Texting isn’t about quantity, it’s about quality.
In this episode, we lay out the new rules of digital conversation: how timing changes tone, why punctuation can send the wrong message, and how to stop overthinking every word.
We also explore the power of mirroring someone else’s texting style and why the pace and platform of your messages can completely shift your vibe. Think of it like a language exchange; you learn to meet someone where they are, digitally speaking.
(32:38) From “Hey” to Real Connection
Let’s be real: no one ever fell in love over a “hey.” If you’ve ever struggled with what to say, how to say it, or whether you should say anything at all, this part is for you.
We break down our go-to formula for starting stronger conversations, the secret to reviving a stalled thread, and how to transition from app to IRL without losing momentum.
It’s not about being perfect, it’s about being clear, consistent, and just a little bit creative.
(41:48) The Rules We Wish Came With Your Phone
If we could send every dater a digital rulebook, this episode might be it. We cover everything from platform progression (yes, there’s a difference between texting, WhatsApp, and a voice memo) to the screenshot test (spoiler: if you wouldn’t want it posted in a group chat, don’t send it).
We even get into the nitty-gritty: when to stop texting and actually meet, how long is too long between dates, and yes—how to bow out gracefully when something’s not working.
This episode is all about using the tools you already have to build the kind of relationships you actually want.
💌 Do you have questions? Damona has the answers!
Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!
The Drew Barrymore Show: Loud Looking and Guest Dating Advice
This week on The Drew Barrymore Show, Damona joined Drew, Valerie Bertinelli, and Ross Mathews for a special makeover episode to help one guest step confidently back into the dating world. Damona shared why being bold, authentic, and unapologetic is the real key to connection — and introduced the idea of Loud Looking for love.
Alongside the glow up reveal, Damona offered encouragement for anyone who’s ever been told they’re “too much” — and why that’s actually a superpower.
Catch all the inspiration, laughter, and dating wisdom by watching the full segment now!
5 Simple Steps to Date Again After a Breakup
Let’s be real: getting back into the dating game after a breakup, divorce, or just a long pause can feel like learning to walk in heels again: awkward, unsteady, and honestly, a little terrifying.
You might be thinking: What if I’m not ready? What if it’s different now?
Spoiler alert: It is different now. But that doesn’t mean you’re not built for it.
Whether you’re in your late 20s, 30s, or 40s, stepping back into dating isn’t about chasing some perfect outcome. It’s about reconnecting with yourself and creating space for something new. And I promise, it doesn’t have to drain your energy or your self-worth.
Here’s how to ease back in without burning out.
1. Give Yourself Permission to Start Slow
You don’t have to rush. You do not have to rush.
Sometimes we need a soft launch back into the dating world. That might look like updating your profile and then ignoring the apps for a week. Or just having a conversation with someone new, no pressure attached.
Check in with yourself. Are you feeling curious? Or does your gut still need a little healing time? That answer will guide your pace, and that pace is perfect.
2. Get Clear on Your Boundaries and Needs
This time, we’re not dating on autopilot. We’re dating with intention.
Ask yourself: What am I available for now? What do I no longer want to entertain? Whether you’re craving connection, companionship, or something more serious, clarity is everything.
Write down your non-negotiables. Keep them in your phone if you need a reminder. These aren’t walls, they’re your guardrails. They help you stay aligned with your values, even when the chemistry’s strong.
3. Try Just One New Way to Meet People
You don’t need to sign up for every app, agree to every setup, or spend your Saturday speed dating unless that lights you up. Choose one way to dip your toe back in.
Maybe it’s attending a local mixer, trying a single dating app, or saying yes to that invite from your social circle. The goal here is simple: show up. Not to impress. Just to connect.
No pressure. No performance. Just presence.
4. Watch Your Inner Dialogue—Before and After Dates
This one’s big. Because the way you talk to yourself shapes the entire experience.
If you catch yourself saying things like “I’m too old for this” or “No one decent is out there,” pause. Gently reframe. Try: “I’m showing up as my full self.” Or “Every interaction teaches me something new.”
Dating is a learning process. And you don’t need to ace every test; you just need to stay kind to yourself between attempts.
5. Celebrate the Small Wins
Not every date will lead to butterflies or a second meeting, and that’s okay. Progress isn’t always flashy. Sometimes, it looks like:
These are wins. Celebrate them. Progress in dating, like in anything else, is built one small courageous act at a time.
Final Thought: Start Where You Are
Dating again isn’t about being “ready” in some mythical, fully healed way. It’s about being willing. Willing to try, to learn, to stay curious.
You don’t have to be fearless. You just have to be you.
So take a deep breath. Set your pace. Keep your boundaries. Talk to yourself with kindness. And celebrate every single step you take back toward love.
Because you’re not starting over, you’re starting from experience.
The Prism & Too Picky
You Are Your Own Magic Wand
Do you feel like you didn’t get dealt the right cards when it comes to love? Maybe your family dynamics, personal history, or past relationships have shaped your path in ways that feel hard to break free from. You’ve done the work therapy, journaling, and mindset shifts, but still feel stuck.
This week on Dates & Mates, New York Times bestselling author and transformational teacher Laura Day joins the show to share how we can begin to shift those long-held patterns and reconnect with our power in love.
Later in the episode, Damona answers a listener’s question about being too picky in dating and how to tell the difference between honoring your standards and blocking your own connection.
(2:06) The Intuition Architect
Laura Day has spent the past four decades helping people sharpen their intuition and transform their lives—from high-profile celebrities to everyday people navigating big transitions. She’s the author of seven books, including Practical Intuition, The Circle, and her newest: The Prism: Seven Steps to Heal Your Past and Transform Your Future.
While she’s long been known for her work in intuitive development, Laura says The Prism came from somewhere more personal.
“This process was what allowed me not only to find a wholeness in myself,” she says, “but also to create what I wanted in my life.”
The book distills her life’s work into a seven-step structure that helps you identify which part of your inner system is driving your decisions—and how to work with it, not against it.
(12:44) Don’t Mistake Familiar for Safe
Let’s talk about patterns. You think you’re making different choices. But the results keep looking strangely similar. It’s not a coincidence.
According to Laura, many of us are wired to recreate the emotional experiences we had early in life, even the painful ones, because that’s what our nervous system knows how to process. Without realizing it, we’re attracted to what’s familiar, not necessarily what’s healthy.
The key is interrupting that loop with new behaviors and new awareness. And no, it does not require perfection or a total overhaul. Just one conscious shift at a time.
(19:47) The “No New Damage” Rule
Ever leave a date feeling off, even when everything “looked good on paper”? Or walk away from a friend hang feeling emotionally hungover?
Laura’s simple but powerful rule: No New Damage
If a person, habit, or dynamic starts eroding your peace, your progress, or your sense of self, pause. Reassess.
“Is your sleep better? Your job going smoother? Are you more emotionally regulated?” Laura asks. “If not, the relationship might be doing harm even if it looks good on paper.”
No new damage doesn’t mean avoiding discomfort. It means protecting your nervous system from relationships that feel more like regression than growth.
(27:22) Your Red Flags Might Not Be Universal
There is a moment in the conversation where Damona and Laura reflect on the lists we make when dating, green flags, red flags, must-haves, dealbreakers, and how rigid those checklists can become.
Laura challenges the idea that love should follow a fixed formula. What one person needs to feel safe or supported might not apply to someone else.
The episode explores how our “non-negotiables” are often built from pain, not clarity, and how real connection happens when we move beyond generalized rules and start tuning into what feels nourishing and sustainable for us as individuals.
(32:18) Rewire, Don’t Rewrite
Change does not have to come from understanding every piece of your past. Sometimes it begins with doing just one thing differently in the present.
Laura shares examples from her own life and relationship, including how she gradually shifted the way she showed up to be more aligned with the kind of love she wanted to co-create.
“There are a lot of great loves out there,” she says. “But what makes someone your person is that you choose them, and you build the structure of love together.”
This episode is not about waiting for fate or finding the perfect partner. It is about stepping into your own power, one choice at a time.
Connect with Laura Day
Website: https://lauraday.com/
Instagram: @lauradayintuit
Book: The Prism: Seven Steps to Heal Your Past and Transform Your Future
(58:11) Dear Damona: Too Picky or Just Discerning?
A listener writes:
“I always thought I’d be married by now, but here I am at 39, still single. I’ve dated great people, but something always felt off. So I kept holding out for the one. Now I’m wondering… was I being too picky, or was I just protecting myself from settling?”
In this week’s Dear Damona, we explore the real difference between high standards and emotional self-sabotage—and why the “spark” might not be the signal you think it is.
💌 Do you have questions? Damona has the answers!
Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!
Coaching Session: Love Intuitive
Trust Your Gut: Unlocking Intuition in Dating
Have you ever had a gut feeling about someone, only to second-guess it later? Wondered if butterflies meant excitement or a warning sign? If so, you’re not alone.
The truth is, intuition isn’t just a vague sense; it’s a powerful internal compass shaped by past experiences, personal values, and subconscious wisdom. But learning how to tune into it, especially in dating, can be a challenge.
This week on Dates & Mates, we offer a rare behind-the-scenes look at an intuitive coaching session with a real client, Mya. With incredible openness and vulnerability, Mya invited us into her journey of learning how to hear and trust her own inner voice in love.
During the session, a powerful question emerged—one that resonates with so many daters today: “How will I know when it’s actually working?”
Settle in, take a breath, and get ready to explore how intuition could become your most important dating superpower.
(2:06) Your Inner Compass Is Speaking (Are You Listening?)
For many singles, intuition is often drowned out by overthinking, self-doubt, or fear.
But as Mya discovered in this session, learning to recognize internal signals—before second-guessing them can make dating feel clearer and more empowering.
Sometimes the answers we’re searching for are already inside us; we just need to learn how to hear them.
(5:00) When Your Body Sends a Message, Believe It
Physical sensations are often the first sign that something is either right or wrong.
Through live exercises with Mya, we explored how subtle feelings like a headache, chest warmth, or a twinge of unease can provide important information about a new connection.
Tuning into these cues can help avoid heartache and steer toward the relationships that truly align.
(14:30) Swipe Fatigue? Your Energy Might Be Trying to Tell You Something
Mya shared that dating apps sometimes left her feeling drained and disconnected, and she’s not alone.
In the session, we unpacked how digital dating overload can mute intuition and why following your energy, not just your inbox, can lead to more fulfilling real-world connections.
When the process starts feeling heavy, it might be your intuition asking for a different approach.
(20:00) How to Know When It’s Working (Even If You Don’t See It Yet)
One of the biggest breakthroughs of Mya’s session centered on redefining success in dating.
Instead of chasing fast results, true progress often looks like building trust with yourself, feeling aligned with your decisions, and moving through dating with confidence, even before the perfect match appears.
Sometimes, the biggest win is learning how to trust the journey.
Experience the full intuitive coaching session with Mya on this week’s Dates & Mates. Learn how to sharpen your inner compass, reconnect with your instincts, and date in a way that feels clear, confident, and true to who you are.
Interested in booking your own solo coaching session?
Email Asst@DamonaHoffman.com or DM @damonahoffman on Instagram or Facebook!
How To Find True Love & IRL Real Deal
Dating Isn’t Broken — But the Fairy Tale Might Be
Dating takes guts—vulnerability, risk, and putting yourself out there—and lately, it’s been feeling a lot.
Between fairy tale myths and the post-lockdown social weirdness, it’s no wonder so many of us feel stuck or just straight-up over it. Swiping feels safer than saying hi, texting is easier than talking, and ghosting? Yeah, it stings.
But here’s the good news: your love story is still yours to write.
This week, TED speaker, podcast host, and modern love expert Francesca Hogi joins me to talk about ditching outdated fairy tales and building real-deal connections. Plus, we tackle a juicy Dear Damona & Dear Franny question: “Dating apps keep feeding me the same old matches. How do I meet someone IRL?”
Take a breath—today’s episode is all about rewriting the rules and stepping into the dating life you actually deserve.
(2:06) Meet Your Dating Reality Check: Francesca Hogi
You might know Francesca Hogi as the host of the Dear Franny podcast, a TED speaker, or the survivor who once literally competed for love on national TV. But today, she’s here wearing another crown: expert guide in tearing down outdated myths about love.
Franny has been featured everywhere from The Today Show to The New York Times, and her new book How to Find True Love is all about giving you the tools to stop chasing fairy tales and start building the real thing.
When she’s not dismantling the “fairy tale industrial complex,” she’s teaching singles how to step back into their power, trust themselves again, and find true love on their own terms.
(2:11) Why Your Love Life Feels Stuck And What Fairy Tales Have to Do With It
From Cinderella to rom-coms, we’ve been sold a very specific idea of what love is supposed to look like: effortless, instantaneous, magical. Francesca calls it the “fairy tale industrial complex,” a billion-dollar business that profits off keeping us chasing a fantasy.
But the truth? Real love doesn’t happen to you. It’s something you build, with trust, respect, and emotional safety at the center.
Franny explains, “When you meet someone, you’re not just admiring their traits, you’re co-creating a whole new relationship. That’s what you actually live inside of.”
(5:00) Are You Dating or Just Swiping?
Sure, dating apps started as a tool. But somewhere along the way, they became a crutch.
Today, many of us feel safer sending a text than making eye contact across a room. Rejection stings less when it’s a silent unmatch rather than a face-to-face conversation. But that “safety” might actually be costing us the very thing we want most: a real connection.
If you’ve ever found yourself stuck in the swipe-scroll-ghost spiral, this part of the episode will hit close to home and offer a way out you might not have considered yet
(12:13) The Self-Love Formula No One Taught You in School
You’ve heard “love yourself first” a million times. But Francesca actually shows you how to do it in a way that’s tangible, empowering, and actionable.
Self-love isn’t about thinking you’re the best person in the room. It’s about treating yourself with the same respect, compassion, and care you wish to receive from others.
As Franny puts it, “You’re not waiting to wake up one day magically feeling worthy. You create that feeling through action, one decision at a time.”
(22:29) How to Meet Cute (Without Feeling Weird About It)
What if every time you stepped outside, you believed something amazing could happen?
Francesca introduces the “Meet Cute Mindset” — a simple but powerful way to move through the world with openness and intention. It’s not about forcing conversations or awkwardly flirting with strangers. It’s about reminding yourself that connection is always possible… if you’re willing to be present enough to notice it.
Spoiler: there’s a cheeky million-dollar thought experiment that might just change how you walk through your local coffee shop tomorrow.
Connect with Francesca:
(38:01) Dear Damona & Dear Franny: Dating Feels Like It’s on Pause
This week’s question comes from Sheryl on Instagram, who shares:
“I use dating apps but remain open to connection when I am out and about. Still, I haven’t met anyone IRL, and my dating apps seem to be repeating candidates I already turned down. My love life feels like it’s on pause. How can I turn it back on?”
If you’ve ever felt like you’re stuck in a loop, seeing the same faces and feeling like real connection is out of reach, this part of the episode will feel like a deep exhale. It’s about shifting from passive hope to active creation and building the kind of dating life you actually want to be living.
Hint: It’s less about chasing outcomes and more about practicing openness, curiosity, and confidence one conversation at a time.
💌 Do you have questions? Damona has the answers!
Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!