Have you ever felt like you’re drowning in matches but starving for actual dates?

You know that feeling when you’re scrolling through your matches and seeing the same faces year after year, app after app. When you’ve got eight plus conversations going but they all seem to fizzle the moment you try to make something real happen.

We’ve been told that more options is always better. That the problem with dating apps is you’re not swiping on enough people or you’re being too picky.

But here’s what happens in real life: having 50 matches doesn’t solve the problem. It just creates a new one. The issue isn’t the number of options. It’s how you move through them.

It’s about what we’re really looking for when we open these apps, what gets in the way of actually finding it, and whether the algorithm is working with you or against you.

This week, a listener wrote in with a situation that so many of you are navigating right now.

She shared:

“I end up with 50 plus matches like within 48 hours. Some of them I suspect are like dead profiles or just the algorithm or robots—literally it’s the same people for years and years. I end up with eight plus conversations and either get too overwhelmed or end up with just a few dead conversations. And then there’s the other situation of having a fantastic phone call, scheduling a date, having him reschedule and ask for a rain date but not give a suggestion. And then there’s another guy I went on a couple dates with five years ago. I see him in a bar, message him on Instagram. He says, definitely, you look great. And then he drops off the conversation when I say, okay, great, let me know when you wanna get together. What is going on?”

This is a question that goes deeper than bad luck with matches: why do options feel like a trap instead of a gift?

(05:00) Maximizers vs. Satisfiers: Why Your Brain Breaks

There are people called maximizers who research everything and want to see all options before deciding.

Then there are satisficers who find an option that works and stop looking.

Here’s the thing: dating apps are built for satisficers. If you’re a maximizer seeing 50 matches, the app doesn’t care that you need more information. It just keeps feeding you more people.

The result? You burn out.

(07:40) No Framework = No Progress

Without a screening system, you start conversations with anyone who looks decent. You’re in eight DMs going nowhere. The potential ones fizzle. The interested ones ghost.

Your screening process needs to be built around your goals and values, not around who’s cute or who has the best text banter.

Ask yourself:

• What are my non-negotiables?
• Do their words and actions match?
• How quickly do they move from chatting to actually making a plan?

When you can answer these, you move through matches with purpose. You tighten your filters. You don’t engage with people who don’t align with what you’re looking for.

(13:00) The Dirty Little Secret About the Algorithm

Dating apps flood you with matches in the first two weeks. When you sign up (or return after time away), the algorithm pushes your profile to everyone. Some profiles are real. Some are dead accounts. Some aren’t people at all.

But the app doesn’t care. It just wants the dopamine hit so you stay and pay.

Two or three weeks in, the options dry up because many weren’t real options to begin with.

What you’re doing by signing on, getting overwhelmed, signing off, and switching to another app is burning your energy. The algorithm never gets a chance to learn who you are. So you end up seeing the same faces year after year because you’re hitting reset every time you take a break.

Give the algorithm time to actually work for you.

(17:00) Interest vs. Intention

Someone can be interested without any intention to follow through. They like the validation. But when it comes time to actually make a plan? They disappear.

Watch what they do, not what they say.

Interest: “You’re amazing, we should definitely hang out.”

Intention: “I’m free Wednesday or Saturday. What works for you?”

One is a feeling. The other is a plan.

When someone disappears the second you ask for specifics, that’s a clear signal. Thank and release them. You are not asking for too much.

(19:00) Coins in a Fountain, Not Fish on a Line

You see someone who looks great and start building a future in your head. You’re already planning your wedding together before you’ve heard their voice.

This is future-casting. And it’s how you lose yourself.

Think of your matches like coins in a fountain. You throw one in and make a wish. Some come true. Some don’t. But you don’t put your whole heart into that coin before you’ve even thrown it.

You’re looking for momentum. You’re looking for consistency. You’re looking for someone whose actions match their words. If you don’t see all three early on—within that first week or two of dating—you’re not going to magically find them later.

Stop waiting for people to show up differently than they already have.

You are not asking for too much when you want someone to actually make a plan. You’re not being too picky when you walk away from people who say “definitely” and then disappear. You’re protecting your time, your energy, and your hope. And that is what matters most.

💌 Got a dating app horror story or match dilemma?

Whether it’s about feeling overwhelmed by options, dealing with flaky behavior, or learning how to protect your energy from the people who drain it, we’re here for all of it.

DM @DamonaHoffman on Instagram, TikTok, or Facebook, or leave a voicemail or text at 424-246-6255. Your question might be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates covers all the relationships that matter in your life—your dating situations, your friendships, your family dynamics, your work relationships, and the relationship you have with yourself.

📝 Want to keep track of what’s working in your dating life? Download the free Date Tracker at damonahoffman.com/datetracker

Why “Mysterious” Often Means “Information Hidden”

What does it really mean to trust someone you’ve never met? And why does your gut feeling matter more than good morning texts?

There’s way more casual digital communication happening now. We’re texting good morning and goodnight to literal strangers. We’re building emotional connections before we’ve even shaken hands. And while much of dating is the same as it was 15 years ago, a few things are different. The stakes are higher. The risks are bigger.

This week, a listener named Jada wrote in with a situation so many are navigating:

“I matched with this guy on Hinge two weeks ago, and the chemistry is amazing. He’s been sending good morning and goodnight texts, asking about my day. But every time I ask where he works, what neighborhood he lives in, or even his last name, he gets vague and says he likes to stay mysterious. My friend says I should know his last name before meeting him. Is that reasonable? How much should I actually know about someone before a first date?”

We’ve been led to believe that the mystery keeps things alive. That asking too many questions or wanting transparency means we’re paranoid, controlling, uptight. That real trust means not verifying who someone actually is.

But here’s what’s really happening: Romance scams have victims losing more than $1.3 billion annually. That’s more than double what we saw before the dating app boom in 2020. The people this is happening to aren’t naive or desperate. They’re hopeful. They’re connecting with someone who feels genuinely real.

It’s about learning what red flags look like in the early stages, how to balance openness with common sense, and understanding that trusting your instincts doesn’t make you paranoid. It makes you smart.

This goes deeper than one match: Can we advocate for what we need without being made to feel like we’re the problem?

(06:00) Give Him the Benefit of the Doubt, But Also Verify

Maybe he’s been burned before. Maybe he’s been manipulated by someone who took advantage of him. Maybe he has a high-profile job, and the second someone figures out how much money he makes, they try to exploit it. Maybe he’s genuinely just been cautious because he’s thinking first of protecting himself.

We can give him the benefit of the doubt and still require information. Those two things aren’t opposites.

Wanting basic information doesn’t make you suspicious

• It makes you smart
• It makes you someone who respects yourself enough to verify
• It makes you someone who (hopefully) won’t end up in a Netflix documentary

But here’s what matters: you need to know more about him before you go offline. This is for your own peace of mind. 

Because how are you going to show up to a date feeling ready to connect if you’ve got this thing in the back of your mind asking, “What is he hiding from me?”

(08:00) The Three Searches That Change Everything

Before you meet anyone in person, gather what you can. Ask for his phone number or email. Then run these searches.

1. PeopleFinders – A quick search on my go-to source PeopleFinders, using their name, phone number, or email, could reveal their address, profession, marital status, financial woes, and criminal record. It’s all publicly accessible.

2. LinkedIn – If they work in any professional field, they likely have a profile. Compare what they told you with what’s listed there. Check recommendations from colleagues. Look for graduation years and employment history. Inconsistencies matter.

3. Reverse Image Search – Save one of their profile pictures and search it on Google Images. Sometimes you’ll find old dating profiles, Facebook accounts, Instagrams (or Finstagrams), maybe even wedding photos, or completely different names. 

If something doesn’t match what they told you, do not explain it away.

(12:00) When the Stories Don’t Add Up

This is where most people mess up: They find conflicting information, and then they rationalize it.

“But I really feel something with this person.”

“Maybe there’s a good explanation.”

“I’ll just ask him about it.”

Don’t do that. Ninety-nine times out of a hundred, discrepancies mean they’re either a catfish, a scammer, or both. 

Either way, do not pass go, abort mission!! No matter how connected you feel over text, no matter how many good morning texts you’ve exchanged, that’s not your person.

Your gut is giving you information worth listening to. Listen to it.

(14:00) You’re Not Paranoid for Wanting Peace of Mind

Let’s settle this once and for all: you are not doing anything wrong by wanting to feel secure before meeting someone face-to-face. It’s not paranoid. It’s not needy. It’s wise. It’s necessary. And I’ve been recommending this for over 15 years.

The way to practice safety is to do just enough research so that you have peace of mind before your date:

• Run PeopleFinders with their name, phone number, or email
• Check their LinkedIn profile for inconsistencies
• Do a reverse image search on their photos
• Schedule a phone call or FaceTime before you meet in person, keep it 15 to 20 minutes (it’s a lot harder to lie or keep stories straight in a real-time conversation than over text).

When you’ve set up this safety net, when you know who they actually are and you’ve heard their voice and verified the basics, you can show up to that date without all the worries and fears. You can just be yourself. You can focus on connecting rather than wondering whether this person is who he says he is. That’s the whole point.

(16:00) The Timeline That Actually Protects You

Once you’ve verified who they are, the hard part is done. Now it’s time to actually go on the date.

First Date Safety Checklist

• Keep that first meeting short. One hour to 90 minutes maximum. 
• Meet him there, not a pick-up from your place or his. 
• Tell a friend exactly where you’re going and share all his details. 
• Bookend the date with somewhere you need to be after so you have a clean exit if something feels off. 
• Meet them solo and leave solo.

This isn’t paranoia. This is you respecting yourself enough to protect your peace. 

When you show up to that date knowing you’ve done your due diligence, knowing they’re real and verified, you can finally just be present. You can have a real conversation. 

You can see if there’s actually chemistry in person instead of just on a screen. And if something feels off in the moment, you trust that too.

Being careful doesn’t mean you’re closed off.

It means you value yourself enough to make informed decisions. And that’s exactly the energy that will serve you best, not just on this date, but in all your relationships.

If you want that peace of mind before your next first date, head to PeopleFinders and try the three-day trial. Once you get in there, you’re going to be hooked. You’re going to be searching up every match you have (and probably some of your friends and neighbors, too)

Trust but Verify at PeopleFinders

When “Touchy Subject” Meets “I Want to Know” Is Curiosity ok??

Ever meet someone you really connect with, but there’s this invisible wall around certain topics? Do you find yourself wanting to know their whole story while also trying to respect the boundaries they’ve set?

You know that feeling when you care about someone and there’s this door that they’re keeping closed? And you don’t know if you’re supposed to knock or just wait for them to open it?

We’ve been navigating relationships our whole lives, trying to balance curiosity with respect. But here’s what happens in real life: sometimes wanting to understand someone deeply can feel like you’re pushing too hard. And sometimes respecting boundaries can feel like you’re being kept at arm’s length.

It’s about timing, trust, and whether two people can build intimacy at a pace that feels safe for both of them.

This week, a listener named Kristen wrote in with a situation that so many of us face in early dating.

She shared:

“I met this guy on Hinge and we’ve gone out on three dates. We’ve talked about some personal things about family and stuff, and we have a lot of things in common. One of the things is we were both raised by single parents and one of the parents he’s not as close to, and he said it’s like a touchy subject for him. So I want to respect that. But I also wanna know a little bit more just to understand how they grew up and how they are as a person and all that jazz, you know?”

This is a question that goes deeper than curiosity: can I honor their boundaries while still protecting myself?

(03:00) “Touchy Subject” Is Actually Information 

When someone tells you something is a touchy subject, they’re not shutting you out. They’re actually giving you valuable information.

They’re setting a boundary clearly instead of letting you stumble into painful territory and possibly shutting down or pulling away.

What they’re really saying is: I have wounds here. I need to feel safe before I can show them to you.

Think of it as a yellow flag: proceed with caution. It’s not a green flag, but it’s definitely not a red one either.

Here’s what most people miss: this is emotional maturity in action. Your job right now? Prove that you are someone who respects boundaries.

(05:00) The Paradox of Protection 

When someone’s past trauma or family wounds come up, those aren’t just facts to them. They’re tender spots.

And yes, you want to protect yourself. You want to know where the landmines are buried so you don’t step on them. That’s completely valid.

But from their perspective:

• What if they tell you something that doesn’t define them, but you treat it like a dealbreaker?
• What if it’s something so shameful to them that they can’t share it yet?
• What if sharing too early means you might pull away?

Here’s the thing: you can actually honor both your curiosity and their boundaries at the same time.

It’s not an either/or. It’s about timing and trust and showing up consistently so that when they’re ready to open that door, you’re there and ready to accept them, warts and all.

(09:00) Slow Love Is Actually Smart Love

Three dates. Meeting once a week. This is actually a really healthy pace.

When you avoid that intense texting all day, seeing each other constantly whirlwind, you give yourself space to actually feel how you feel about someone between dates.

Deep family trauma? That’s probably not on the table yet. It might not even be on the menu.

And that’s okay. You’re still in the getting to know you phase. You’re learning. You’re figuring out if date three built on date two, and if you feel more yourself, more comfortable, more safe.

When you rush the timeline, you create false intimacy that makes people overshare before trust is built. Slow love gives both people time to build that foundation, little by little, brick by brick.

(13:00) Small Moments Build Big Trust 

Here’s the thing about proving you’re trustworthy: it doesn’t happen in one big vulnerable share. It happens in all the small moments.

Every time you see him and don’t push on that touchy subject? You’re laying another brick. Every time you share something vulnerable about yourself first and see how he holds that? Another brick.

One thing you can do: talk a little more about being raised by a single parent. Not as a way to get him to reciprocate, but as a genuine offering.

When you model vulnerability, you’re essentially saying, this is safe territory. I have walked this path too. And when you’re ready, I am here.

That’s how you create a space where emotional honesty feels safe, not scary.

(15:00) Permission to Not Know Everything Yet 

Here’s your permission slip: it is okay not to know everything about someone after just three dates.

The three date rule is about figuring out if you want to keep going, not about having already arrived. That’s really where the deeper levels of sharing begin.

And honestly? If someone shares their deepest wounds in the first three dates, that can actually be a red flag that they haven’t processed them yet.

Mystery isn’t the enemy of connection. Premature oversharing is.

Trust isn’t built in one conversation. It’s built in a thousand small moments of showing up and respecting the boundaries people set.

Your curiosity is valid, and so is their need for safety. The key is showing up consistently and honoring both.

💌 Got a question about boundaries, early dating, dating horror stories, or when to share what?

Whether it’s about respecting someone’s pace, knowing when to ask deeper questions, or figuring out if you’re being too curious or not curious enough, we’re here for all of it.

Send your question in a DM or voice memo on  Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates isn’t just about romantic relationships anymore. It’s about the people who matter most: partners, friends, family, coworkers, and you.

📝 Want to keep track of what’s working (and what’s not) in your love life? Download the free Date Tracker at damonahoffman.com/datetracker

Have you ever been stuck managing someone else’s emotional chaos when you’re just trying to get your work done?

This week we’re tackling a different kind of relationship, one that sometimes gets overlooked: the one between you and your boss. 

We talk a lot about emotional safety and clear communication, especially in romantic relationships. But what happens when someone in a professional setting starts treating you like their therapist or their best friend? And you can’t just hit mute, unsubscribe, block and delete and walk away.

Listener Linda is dealing with exactly this:

“My boss is nice, but she talks to me like I’m her best friend—like way too much info. Relationship issues, family drama, sometimes mid-meeting she’ll start telling a story that’s got nothing to do with work. It’s super uncomfortable, but I also don’t wanna create tension or seem like I’m judging her. How do I keep things professional when the person in charge doesn’t seem to know where the line is?”

If you’ve ever felt caught between empathy and awkwardness at work, you’re not alone. And no, you’re not being cold for wanting boundaries. You’re being honest.

(3:00) When “Nice” Doesn’t Mean “Safe”

Here’s something most people miss: just because someone feels safe around you doesn’t mean they’re creating a safe space for you.

Linda’s boss probably thinks she’s building trust. But what’s really happening? Emotional dumping. She’s offloading her personal problems onto someone who doesn’t have the power to say no or redirect without risking her job. That creates an imbalance of power.

When your boss overshares, you end up managing their discomfort instead of acknowledging your own. You’re trying to make them feel okay while you feel increasingly uncomfortable yourself.

(5:00) The Post-Pandemic Boundary Blur

Remember about five years ago when something completely changed the way we work? Yeah, the pandemic.

When everyone shifted to working from home, the lines between personal and professional actually got clearer. You had to make deliberate choices about whether to use meeting time for personal conversation or stay focused on tasks.

But now that people are back in the office? All bets are off. The lines are blurred again.

When those expectations don’t match, one person thinks they’re bonding while the other is just trying to get through their to-do list.

(8:00) You’re Not Being Selfish, You’re Being Clear

Look at what Linda said: “It’s super uncomfortable, but I also don’t wanna create tension.”

Do you hear what’s happening? She’s prioritizing her boss’s comfort over her own.

This pattern shows up everywhere. In romantic relationships, at work, and with family. We don’t say what we’re really feeling because we’re worried about the repercussions.

But here’s the truth: boundaries don’t make you cold. They make you trustworthy because people know where they stand with you.

(10:00) Three Ways to Redirect Without Drama

What do you actually do when your boss starts oversharing? You have options that don’t require confrontation.

• Subtle Redirection in the Moment: Acknowledge what she said, then redirect: “Wow, that sounds like a lot. So should we circle back to the budget review?”
• Set Timing Boundaries: Create a container: “Hey, I want to give this project my full attention. Can we pick this up after five?” You’re not saying no. You’re just saying not right now.
• Clear But Compassionate Reframe: For persistent oversharing: “I really value working with you, but when we bring personal challenges into the workplace, I’m not able to stay focused and do the best job for you. Maybe we can reframe our conversations to stay focused on the work.”

(16:00) Why This Matters Beyond Your Job

How you handle boundaries at work shows up everywhere else in your life.

If you’re stuffing down your feelings to keep the peace with your boss, you’re probably doing it in your romantic relationships too. 

Practice boundary setting here so you can practice it everywhere.

You’re allowed to protect your peace. Even if it’s awkward. Even if the person crossing the line is technically above you.

Professionalism and compassion are not mutually exclusive.

Workplace boundaries aren’t about being difficult.

They’re about protecting your capacity to do good work while maintaining your emotional well-being. Honoring your boundaries is the most compassionate thing you can do for everyone involved.

💌 Ask us anything…don’t be shy!

Whether it’s about dating, relationships, navigating a tricky boss, or what the heck to say when someone crosses a line, we’re here for all of it.

Send your question in a DM or voice memo on  Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates isn’t just about romantic relationships anymore. It’s about the people who matter most: partners, friends, family, coworkers, and you.

📝 Want to keep track of what’s working (and what’s not) in your love life? Download the free Date Tracker at damonahoffman.com/datetracker

Your best friend knows everything about you except the one thing that could change everything between you.

Your best friend is the safest relationship in your life. People already think you’re dating. You can finally picture a future with someone, except there’s one problem: she’s straight, and you’re terrified that telling her how you feel will destroy everything.

This week, a listener wrote in about being in love with her best friend:

“I’m a queer woman in my thirties and my best friend is straight. We’ve gotten so close that people think we’re dating. My therapist says she’s the safest relationship I have. I think she’s my person. I’ve never been able to visualize a long-term relationship before this. But it’s getting harder to listen to her talk about dates with men. Do I tell her how I’m feeling and risk our friendship? Or do I stay quiet and protect my heart while keeping this incredible friendship I never want to lose?”

If you’ve ever questioned whether safety means compatibility, or wondered if speaking your truth is worth the risk, here’s what you need to know.

(3:00) When “Safe” Doesn’t Mean “The One”

Emotional safety is foundational for any relationship, but it doesn’t automatically mean you’re meant to date someone. This is one of the biggest areas of confusion when friendship starts to feel like something more.

If you’ve had past relationships where safety was missing, of course a friendship that offers that security feels extraordinary. 

But safety is just the baseline. It’s what allows you to be vulnerable, to show up authentically, to actually connect. The real question isn’t “Do I feel safe with this person?” It’s “What else is here beyond safety?” Is there mutual attraction? Reciprocity? Actual romantic possibility?

Just because someone checks the safety box doesn’t mean they check all the boxes you need for a romantic partnership. Safety gets you in the door, but it’s not the same thing as compatibility.

(6:30) The Fantasy Bubble Is Keeping You Stuck

Here’s the uncomfortable truth: it’s easy to picture a perfect relationship with someone when you’re already suspecting they’re not interested. 

You get to stay in the fantasy where everything is beautiful and uncomplicated because you’re not dealing with the messy reality of an actual relationship.

Real relationships come with logistics. They come with disagreements about how to spend holidays, different communication styles, navigating conflict, making compromises. Fantasy relationships don’t have any of that. They stay perfect in your mind because they’re not real.

As Damona explains: “You’re in the fairytale, you’re in the story that you’re writing, and you’re not popping that bubble with logistics and realities.”

And here’s what makes it even more complicated: sometimes we’re actually attracted to the impossibility. That will-they-won’t-they energy can be addictive. It’s the thrill of the chase without the vulnerability of actually being seen and chosen. Or rejected.

But staying in that fantasy keeps you emotionally unavailable to real possibilities elsewhere. 

(10:00) Before You Confess: Play Out Every Scenario

Before you tell your best friend how you feel, you need to sit with every possible outcome. Not to catastrophize, but to actually prepare yourself emotionally for what could happen next.

• Scenario one: She says she’s straight and this isn’t going anywhere. She loves your friendship, but she can’t reciprocate romantic feelings. Could you handle hearing that and still show up as her friend? Or would knowing that answer make it impossible to continue?
• Scenario two: She feels uncomfortable knowing you’ve had romantic feelings this whole time. Maybe she starts to question every moment you’ve shared, wondering if your friendship was genuine or if you were just waiting for your chance. She might pull away without even giving you closure.
• Scenario three: She’s intrigued. She hadn’t thought about you that way, but maybe she’s open to exploring it. Are you ready to navigate what it means to be someone’s first relationship with a woman? That comes with its own complexity.
• Scenario four: The fantasy. She’s been in love with you too, just waiting for you to say something. What’s the actual likelihood of this outcome compared to the others?

You need honest answers to these questions before you speak. Not to scare yourself, but to know what you’re truly willing to risk and what you’re not. And to understand that telling her might give you clarity, but it also might give you loss.

(13:00) The Cost of Staying Silent Is Higher Than You Think

Here’s what’s already happening, even without you saying anything: you’re avoiding conversations about her dating life. 

You’re not asking the questions a good friend would ask because hearing about her dates with men is too painful. You feel like you’re not being a good friend, and you’re right. The friendship you’re trying to protect is already changing.

Damona reminds us: “Not telling her doesn’t make the feelings go away, and telling her isn’t a magic pill.”

There’s also another cost: staying in this dynamic keeps you emotionally unavailable. You’re so invested in this person who might not be available to you romantically that you’re not open to meeting someone who actually could be your person. Someone who would choose you back without hesitation.

The real question isn’t whether silence protects the friendship. The real question is: what are you more afraid of? Losing the friendship, or continuing to hide and slowly losing yourself in the process?

(17:00) Create Distance Before You Decide Anything

Before making any declarations, do something that might feel counterintuitive: create space. Not forever, and not in a way you have to explain, but intentionally step back for a bit.

When you spend constant time with someone, there’s a biological and energetic exchange that happens. You start to sync up, to become almost symbiotic. That closeness can make it impossible to see clearly what’s actually there versus what you want to be there.

Distance gives you perspective. When you’re not in the thick of the friendship, when you’re not getting that regular hit of connection and intimacy, you can assess more honestly. 

Are you still obsessing when you’re apart? Do you still feel that pull? Or does it feel more situational, something that intensified because of proximity rather than genuine romantic compatibility?

Get some distance, then check in with yourself. Do you need to speak up about this? Or is this something that’s more in your head than in reality? Once you have that clarity, you’ll know what to do next

💌 Have a question about dating, relationships, or any connection that matters to you?

Damona’s ready to help.

Send your question in a DM or voice memo on  Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

Dates & Mates has evolved beyond just romantic advice… Now we’re exploring all the relationships that shape your life: romantic partners, friendships, family dynamics, and your relationship with yourself..

📖 Ready to challenge the stories that might be holding you back in love?

Check out Damona’s book “F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”  for a fresh take on modern relationships and the courage to rewrite your own love story.

When Good On Paper Feels Empty Inside

You’ve done everything right. You’ve clarified your values, opened your heart to new possibilities, and even followed the three-date rule. But there you are, sitting across from someone who checks all the boxes while your heart whispers “meh.”

This week’s Dear Damona question comes from Taylor who’s wrestling with a frustration that hits so many intentional daters:

“I recently met a decent man who broadly matched my goals and values, was a good communicator, reliable, etc. I went on three dates, but each time I felt like I was dragging myself. I wasn’t excited to be with him, but I pushed through because I remembered your advice on giving it three dates when there’s no chemistry to see if it will build. Upon reflection, I’ve realized sense of humor is really important to me. If a man can’t make me laugh or at least find my jokes funny, I struggle to feel a connection. But I’m worried that I’m letting decent men slip by just because they’re not funny.”

Sound familiar? Let’s talk about what happens when compatibility meets reality, and why trusting your gut doesn’t make you too picky.

(00:05:00) The Three-Date Rule Has One Big Caveat You Might Be Missing

Here’s what most people get wrong about the three-date rule: it’s not about grinding through three painful encounters because someone told you to. The magic word here is CURIOUSITY.

If you’re feeling dread about seeing someone again, if you’re checking the clock during dinner, if you feel depleted rather than energized after spending time together, you already have your answer. 

“The three-date rule is if you are not curious about them after the third date, and you’ve given it those three dates to not only get to know them, but to also open up yourself,” Damona explains.

Because here’s the thing: you might not be fully yourself on date one either.

The rule exists to give both people space to get comfortable and reveal who they actually are. It’s not a prison sentence that forces you to power through misery in the name of being “open-minded.”

(00:14:00) Your Body Knows Before Your Brain Catches Up

Want a foolproof way to gauge connection? Do an energy check the moment each date ends. Not tomorrow, not when you get home and overthink it. Right when you get in your car or step onto the train.

Ask yourself: Do I feel more open or more closed after spending time with this person? Am I energized or completely drained? Your immediate physical response will tell you everything you need to know about compatibility.

This is exactly why our free Date Tracker tool includes space to capture these energy shifts while they’re fresh, so you can spot patterns about what types of people actually enhance your life.

Just make sure you’re not in a season of general malaise that might be clouding your judgment. If you’re feeling “blah” about work, friends, and everything else in your life, you might need a dating pause rather than a new person to fix your energy.

(00:16:00) Why Humor Isn’t Shallow (It’s Actually Genius)

Before you feel guilty about wanting someone who makes you laugh, understand what humor really reveals. 

It’s not just about entertainment. It’s a sophisticated compatibility test that shortcuts months of getting-to-know-you conversations.

Shared humor signals shared experiences, cultural understanding, and similar worldviews. When someone gets your joke, they’re showing you they speak your language on multiple levels. When they don’t, you’re discovering a fundamental disconnect.

“Humor actually demonstrates some other things that are really important in compatibility,” Damona notes. “Humor is a sign of shared experience. One of the reasons that you don’t find someone’s humor funny is because you might not be able to relate to it.”

But here’s where it gets deeper: humor is one of the few ways we show bravery in everyday life. When you tell a joke, you’re taking a social risk. When someone doesn’t acknowledge that risk or meet you where you are, it leaves you feeling exposed and disconnected.

(00:22:00) Decent Is the Bare Minimum, Not the Goal

Let’s address the guilt you’re carrying about “letting decent men slip by.” Here’s your reality check: everyone should be decent. 

Kindness, reliability, and basic communication skills aren’t special qualities that deserve a gold star. They’re the cost of entry.

You’re not being too picky when you want more than the basics. You’re recognizing that you deserve the extras, the upgrades, the things that make someone not just a match, but a match for you.

Stop normalizing decency as something to be grateful for. Start expecting it as the foundation upon which everything else gets built. The chemistry, the humor, the intellectual connection, the way they make you feel seen and understood. Those aren’t bonuses. Those are the real relationship goals.

(00:25:00) Why You Can’t Pre-Screen for Chemistry (And Should Stop Trying)

Stop trying to assess compatibility through texts, dating profiles, or even FaceTime calls. You cannot accurately judge someone’s humor, conversational skills, or chemistry until you’re face-to-face.

• That hilarious texter who goes silent in person? 
• The witty profile writer who can’t think on their feet during dinner? 
• The charming phone conversationalist who has zero physical presence? 

You’ve probably met them all.

So save yourself the false hope and get to the in-person meeting as quickly as possible. Match, maybe do one screening call, then meet within a week. Everything else is just delayed disappointment.

Trust the process: goals and values can be discussed on paper (or on screen), but to get to the other pillars of long-term compatibility from F the Fairy Tale, you have to feel someone out. And when it doesn’t feel right, don’t override your intuition with logic. Your body is giving you information that your brain can’t argue with.

💌 Have a relationship question that’s been weighing on you?

From dating dilemmas to family dynamics, friend boundaries to figuring out the right response to that confusing text, Damona wants to hear it all.

Send your question in a DM or voice memo on  Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

Remember: Dates & Mates covers every relationship that shapes your world. Romantic partners, friendships, family connections, and most importantly, your relationship with yourself.

📝 Want to keep track of what’s working (and what’s not) in your love life?

Get your free Date Tracker at damonahoffman.com/datetracker

📖 Get a copy of Damona’s book to learn more about the Three Date Rule and how to find love successfully:

“F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”