A 4th Generation Matchmaker’s Tried-and-True Dating Tips
What happens when 60% of the single population thinks swiping while watching Netflix counts as putting yourself out there?
This week’s Dates & Mates guest, fourth-generation Matchmaker Maria, dropped some hard truths that might sting a little.
Her new book “Ask A Matchmaker” has already gotten hundreds of people into relationships in just four months. That’s because she’s not here to sugarcoat the reality of modern dating.
When Maria says “a lot of people are participating in dating by laying on their couch and swiping on profiles while a rerun of The Office is playing in the background,” she’s talking about most of us. But here’s the thing: this isolation isn’t entirely our fault.
We’ve accidentally designed a society that cuts us off from the natural ways humans used to meet. And it’s costing us connections we desperately need.
(00:02:20) Meet the Fourth-Generation Matchmaker Who’s Seen It All
Maria’s family has been bringing people together since before dating apps existed. Her great-grandmother was a matchmaker. Her in-laws met through a matchmaker in 1976. Her parents met at a friend’s party in 1983 without one.
Now she’s putting 15 years of matchmaking wisdom into her brand new book, “Ask A Matchmaker: Matchmaker Maria’s No-Nonsense Guide to Finding Love.” In just four months since release, it’s already gotten hundreds of people into relationships because Maria doesn’t sugarcoat the hard truths about modern dating.
That seven-year gap between her parents and in-laws tells the whole story of how we got here. “Even when you get away from arranged marriages,” Maria explains, “people were meddling in their lives. With my in-laws, their parents were involved. The neighbors knew about it. The cousins had opinions.”
Her parents’ “love marriage” still had community support. Friends arranged group outings. People called the same mutual friend for intel. There was gossip, opinions, and awareness of shared values.
That’s what we lost: the village that used to meddle in your love life.

(00:05:58) Why You’re Dating Alone (And Why That’s the Problem)
The majority of single people are participating in dating by themselves. Not just physically alone on their couch, but emotionally alone in the process.
“Something like 60, 70, 80% of people are online dating,” Maria notes. “I say in the book, don’t think of it as a dating app. Think of it as a meetup app.”
But we’ve created what Damona calls “siloization” in every part of our lives. You can’t call someone without permission. You can’t drop by a neighbor’s house. Your windows are up, your air conditioning is on, and nobody’s walking by to say hello.
The nuclear family became the only family that mattered. Meanwhile, every other Western nation still has grandparents, cousins, aunts, and uncles living on the same street.
We’ve optimized for convenience and privacy, but we accidentally optimized out connection.
(00:18:33) Your Algorithm Is Making You Lonelier
Here’s something that will make you uncomfortable: ask your friends to show you their Instagram explore pages next time you’re out together.
Most people won’t do it. It’s literally the most intimate thing you could ask for. And that algorithm is feeding everyone the most extreme viewpoints possible, creating silos of beliefs that keep us isolated.
You’re taking in stories from Instagram, TikTok, rom-coms, and fairytales without realizing what diet you’ve fed yourself. Then you operate from those beliefs, making assumptions about people based on political affiliation or lifestyle choices without ever getting to know them.
(00:24:34) The Five Pillars That Actually Predict Relationship Success
Forget “tall, dark, and handsome.” After 15 years of matchmaking, Maria has identified what actually matters: physical, spiritual, intellectual, emotional, and financial compatibility.
Physical isn’t just attraction—it’s safety and respect. Men assess attraction in four seconds. Women assess safety. Both happen in the first 40 seconds of meeting.
Spiritual is soul connection, not religion. “Do you feel a connection? Were you meant to meet this person in this lifetime? You can tell this by the end of the first date.”
The last three keep relationships going long-term. Intellectual means shared humor and growth, not degrees. Emotional covers self-awareness and conflict resolution. Financial is about lifestyle and values around money, not income.
“When you go through the book, it’s very introspective. It’s deeply personal to the reader,” Maria explains. You write down what’s ping-ponging in your head and get clarity on who you’re actually meant to be with.
(00:33:30) Why Deep Text Conversations Count for Nothing
Maria’s famous 12-date rule has gotten thousands of people engaged. Wait 12 dates before becoming intimate, but here’s the catch: she defines what counts as a date:
- A phone call, video call, or in-person date lasting a minimum of 20 minutes, maximum 3 hours.
- You can have two dates in one day.
- Three out of 12 dates must be in-person.
- Most people complete it in two to three weeks.
And before you ask: “Deep text conversations count for nothing. And audio messages count for shit too.”
Why does this work? “You’ve now given yourself a challenge to intentionally get to know someone,” Maria says. You’re looking for four things: how they act on their bad days, their good days, your bad days, and most importantly, YOUR good days.
You discover a lot about someone when you’re not thinking about having sex with them.
📲 Connect with Matchmaker Maria
Get the book Ask a Matchmaker by Matchmaker Maria
Connect with Maria on Instagram. Facebook, and TikTok
💌 Got a communication question you’ve been sitting on?
Whether it’s about dating, relationships, boundaries, or what the heck to text back… Damona’s 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, and you.
📝 Want a better way to track what’s working (and what’s not) in your love life?
Get your free Date Tracker at damonahoffman.com/datetracker
The Best Friend Fantasy & Safest Situation
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.
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.
Access Daily: Modern Dating Slang & Dating Costco Style
Damona Takes on Modern Dating Culture with Access Daily
Damona joined Kit Hoover and Mario Lopez on Access Daily for a conversation that mixed humor with hard-hitting dating strategy.
The topic that got everyone talking? A new study suggests you’re actually more likely to meet someone at Costco than through a dating app. Damona flipped the script: “I think of dating like marketing. You want to be somewhere where there’s high volume, low competition.” Her advice? Think beyond the apps and consider places like Home Depot on a Saturday—where the odds might actually be in your favor.
From there, the conversation shifted to the wild world of dating terminology. Damona broke down “flood lighting” (when someone overshares so much on a first date that it’s blinding instead of revealing) and “hat fishing” (when the baseball cap comes off and surprises follow). But the real message landed when she talked about ghosting culture. With a quarter of singles experiencing it, Damona believes a dose of humor might be exactly what we need to call out bad behavior and actually create change.
Watch the full segment HERE!
The Efficiency Trap & The Loneliness Gap
You’re Managing Life Together, But Are You Actually Living It?
Have you ever felt like you and your partner have become the world’s most efficient roommates?
You’ve got the logistics down to a science (bills paid, kids shuttled, house maintained) but somewhere along the way, you stopped being lovers and became project managers.
This week, a listener named Shelly perfectly captures what so many of us experience but rarely name out loud:
“I’m lonely in my own marriage. We’ve been together 12 years and we’re like this well-oiled machine. Kids get to practice, bills are paid, house doesn’t fall apart, but that’s it. We don’t actually talk anymore, just coordinate. Last week I realized we hadn’t had a real conversation in probably two months. When I brought it up, he was like, ‘what’s wrong? We’re good. We don’t fight.’ But I’m dying here. I miss my husband.”
Her story hits at something most couples face but few discuss: the efficiency trap that slowly replaces emotional intimacy with tactical coordination. Here’s how to recognize it, understand it, and most importantly, how to climb back out.
(3:00) The Corporate Marriage Trap
What got you here won’t get you there, and nowhere is this more true than in long-term relationships.
Shelly and her husband have developed “badass skills” that make them incredible co-parents and co-managers. They’re like a well-run corporation, but corporations don’t cuddle.
The problem isn’t that you’re good at logistics. The problem is when logistics become your only shared language.
“Dating is a set of learned skills, and relationship-ing is also a set of learned skills,” Damona explains. But here’s the kicker: we get relationship amnesia. We forget to practice the very skills that brought us together in the first place.
Think about it: you actively practice intimacy in the beginning because everything is new and uncertain. But once you’ve mastered the day-to-day operations, intimacy starts feeling optional instead of essential.
(5:00) Scheduling Intimacy Isn’t Unsexy (It’s Strategic)
Here’s something that might blow your mind: you need to schedule intimacy the same way you schedule soccer practice and financial conversations. And no, this doesn’t just mean putting sex on the calendar (though that works for some people… shout out to the “afternoon delight” and “Shabbos naps”).
This means carving out time where someone else handles the logistics while you focus solely on each other as a couple. “It is really hard to feel connected, feel sexy, or feel intimate when you’re thinking about all of the things on your to-do list,” Damona points out.
The homework here is powerful: think back to when you felt most seen and connected. What were the circumstances? What made you feel free? What elements can you recreate right now?
Because when you can get specific about what you’re missing, you can fill that hole. But if you don’t know where the hole is, it just becomes quicksand.
(9:00) When “We’re Good” Means “I’m Drowning”
Things get tricky here… When Shelly brought up feeling disconnected, her husband’s response was classic: “What’s wrong? We’re good. We don’t fight.” Sound familiar?
This is the disconnect that kills relationships slowly: one person feels completely satisfied with a functional partnership while the other is starving for emotional connection.
He didn’t know it was test day; he thought he was just showing up to class. Meanwhile, she’s been keeping a mental tally of every missed connection.
The solution isn’t avoiding this conversation (it’s having it differently). Instead of “we are disconnected,” try “I feel disconnected.” Instead of assuming mutual understanding, start from your own experience: “I want to feel closer and regain a sense of intimacy. How can we work together to change this?”
(12:00) Two Months Without a Real Conversation
Let that sink in for a moment. Two months. In a marriage. Without a real conversation.
This isn’t just busy schedules (this is an emotional drought). And the scary part is how gradually it happens.
You look up one day and think, “Wait, how did we get so far apart?” Real conversation means sharing thoughts, feelings, dreams, fears… not just who’s picking up the milk.
The question becomes: are you willing to be brave and vulnerable with your partner to receive some bravery and vulnerability back?
When all your interactions become transactional, you lose the emotional intimacy that makes a partnership feel like partnership. And the longer you go without meaningful connection, the harder it becomes to remember how to restart these conversations.
(14:00) Missing Someone Who’s Right Next to You
“I’m dying here. I miss my husband.” This line captures something most people feel but don’t know how to say. You miss the person you fell in love with, and they’re sleeping right next to you every night.
Loneliness in marriage can feel just as painful as loneliness when you’re single because the person you need is so close, but emotionally unreachable. It’s a sign that person-to-person connection is being replaced by role-to-role interaction.
But here’s the good news: the person you love is still in there. They’re still right there.
Damona shares her own story of maintaining connection during physical separation, emphasizing the power of getting from the action to the emotion underneath it.
When you can communicate how something makes you feel rather than just what you need them to do, everything shifts.
💌Got a communication question you’ve been sitting on?
Whether it’s about dating, relationships, boundaries, or what the heck to text back (Damona’s 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, and you).
📖 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.
We’re Signal Award Finalists – And We Need You
The Scrappy Indie Podcast Needs Your Vote
Big news: Dates & Mates is a Signal Award finalist!
This is our first major award nomination ever, and we’re the ONLY independent podcast nominated in our category. While the other nominees have network backing and corporate budgets, we have something better – a community that shows up for real talk about love.
This recognition belongs to everyone who’s been part of this journey, sharing stories and trusting us with their most vulnerable relationship questions.
If this show has ever helped you, inspired you, or changed how you think about love – this is your moment to show up.
Voting is open through October 9th and every single vote matters.
Go to damonahoffman.com/award to vote – it takes less than 30 seconds.
Let’s show the podcasting world what authentic community looks like.
Good on Paper & Sixth Sense of Humor
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.
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”
The 12 Date Rule & Matchmaker Maria
A 4th Generation Matchmaker’s Tried-and-True Dating Tips
What happens when 60% of the single population thinks swiping while watching Netflix counts as putting yourself out there?
This week’s Dates & Mates guest, fourth-generation Matchmaker Maria, dropped some hard truths that might sting a little.
Her new book “Ask A Matchmaker” has already gotten hundreds of people into relationships in just four months. That’s because she’s not here to sugarcoat the reality of modern dating.
When Maria says “a lot of people are participating in dating by laying on their couch and swiping on profiles while a rerun of The Office is playing in the background,” she’s talking about most of us. But here’s the thing: this isolation isn’t entirely our fault.
We’ve accidentally designed a society that cuts us off from the natural ways humans used to meet. And it’s costing us connections we desperately need.
(00:02:20) Meet the Fourth-Generation Matchmaker Who’s Seen It All
Maria’s family has been bringing people together since before dating apps existed. Her great-grandmother was a matchmaker. Her in-laws met through a matchmaker in 1976. Her parents met at a friend’s party in 1983 without one.
Now she’s putting 15 years of matchmaking wisdom into her brand new book, “Ask A Matchmaker: Matchmaker Maria’s No-Nonsense Guide to Finding Love.” In just four months since release, it’s already gotten hundreds of people into relationships because Maria doesn’t sugarcoat the hard truths about modern dating.
That seven-year gap between her parents and in-laws tells the whole story of how we got here. “Even when you get away from arranged marriages,” Maria explains, “people were meddling in their lives. With my in-laws, their parents were involved. The neighbors knew about it. The cousins had opinions.”
Her parents’ “love marriage” still had community support. Friends arranged group outings. People called the same mutual friend for intel. There was gossip, opinions, and awareness of shared values.
That’s what we lost: the village that used to meddle in your love life.
(00:05:58) Why You’re Dating Alone (And Why That’s the Problem)
The majority of single people are participating in dating by themselves. Not just physically alone on their couch, but emotionally alone in the process.
“Something like 60, 70, 80% of people are online dating,” Maria notes. “I say in the book, don’t think of it as a dating app. Think of it as a meetup app.”
But we’ve created what Damona calls “siloization” in every part of our lives. You can’t call someone without permission. You can’t drop by a neighbor’s house. Your windows are up, your air conditioning is on, and nobody’s walking by to say hello.
The nuclear family became the only family that mattered. Meanwhile, every other Western nation still has grandparents, cousins, aunts, and uncles living on the same street.
We’ve optimized for convenience and privacy, but we accidentally optimized out connection.
(00:18:33) Your Algorithm Is Making You Lonelier
Here’s something that will make you uncomfortable: ask your friends to show you their Instagram explore pages next time you’re out together.
Most people won’t do it. It’s literally the most intimate thing you could ask for. And that algorithm is feeding everyone the most extreme viewpoints possible, creating silos of beliefs that keep us isolated.
You’re taking in stories from Instagram, TikTok, rom-coms, and fairytales without realizing what diet you’ve fed yourself. Then you operate from those beliefs, making assumptions about people based on political affiliation or lifestyle choices without ever getting to know them.
(00:24:34) The Five Pillars That Actually Predict Relationship Success
Forget “tall, dark, and handsome.” After 15 years of matchmaking, Maria has identified what actually matters: physical, spiritual, intellectual, emotional, and financial compatibility.
Physical isn’t just attraction—it’s safety and respect. Men assess attraction in four seconds. Women assess safety. Both happen in the first 40 seconds of meeting.
Spiritual is soul connection, not religion. “Do you feel a connection? Were you meant to meet this person in this lifetime? You can tell this by the end of the first date.”
The last three keep relationships going long-term. Intellectual means shared humor and growth, not degrees. Emotional covers self-awareness and conflict resolution. Financial is about lifestyle and values around money, not income.
“When you go through the book, it’s very introspective. It’s deeply personal to the reader,” Maria explains. You write down what’s ping-ponging in your head and get clarity on who you’re actually meant to be with.
(00:33:30) Why Deep Text Conversations Count for Nothing
Maria’s famous 12-date rule has gotten thousands of people engaged. Wait 12 dates before becoming intimate, but here’s the catch: she defines what counts as a date:
And before you ask: “Deep text conversations count for nothing. And audio messages count for shit too.”
Why does this work? “You’ve now given yourself a challenge to intentionally get to know someone,” Maria says. You’re looking for four things: how they act on their bad days, their good days, your bad days, and most importantly, YOUR good days.
You discover a lot about someone when you’re not thinking about having sex with them.
📲 Connect with Matchmaker Maria
Get the book Ask a Matchmaker by Matchmaker Maria
Connect with Maria on Instagram. Facebook, and TikTok
💌 Got a communication question you’ve been sitting on?
Whether it’s about dating, relationships, boundaries, or what the heck to text back… Damona’s 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, and you.
📝 Want a better way to track what’s working (and what’s not) in your love life?
Get your free Date Tracker at damonahoffman.com/datetracker
I Miss You Taboo & The Bro Barrier
The “I Miss You” That Changed Everything
What happens when three simple words carry the weight of decades of gender norms?
This week’s Dates & Mates conversation started with one casual moment between a husband and wife that opened up something much bigger.
When friend of the show Douglas asked his wife how a plan with an acquaintance came together and she said, “I just got a text that said ‘I miss you,’” it sparked a debate that many people, especially men, are quietly carrying.
“I told her it’s nice that women can just text ‘I miss you’ to each other because guys can’t do that,” Douglas said. “She insisted that we could. But I’m not convinced.”
Let’s talk about what’s really stopping us from connecting and how we can start changing it.
(2:10) The Gender Divide That Silences “I Miss You”
There’s a reason it feels easier for women to say “I miss you.”
Many of us were socialized from a young age to express our emotions, nurture friendships, and use affirming language with each other. That doesn’t mean we all do it perfectly, but the cultural permission is there.
Men, on the other hand, often learn that bonding should happen through action, not vulnerability. So when a man says “I miss you,” it risks being misunderstood or even rejected.
What’s stopping many of us from deeper connection isn’t emotional incapacity. It’s social conditioning. And it’s costing people relationships they need now more than ever.
(5:45) The Friendship Recession Is Real
In the 1990s, over half of men said they had six or more close friends. By 2021, that number had dropped to 27%. Now, one in six men in the U.S. reports having zero close friends.
That’s not just sad. It’s dangerous. Because the emotional suppression that begins in childhood often turns into loneliness, anger, and disconnection later in life.
“I talk a lot about how we expect our partners to be everything: best friend, emotional confidant, romantic connection, but that’s not sustainable,” Damona says in the episode. “We need a constellation of care.”
And yes, that includes friendships.
(10:30) Yes, You Can Text First
Reaching out to an old friend or starting a new one might feel like an emotional mountain. But the first step doesn’t have to be dramatic.
Here are a few text ideas that feel real but not risky:
You don’t need to say “I miss you” right away. But saying something is a good place to begin.
(14:45) How to Rebuild Friendship One Activity at a Time
If you’re someone who struggles with staying in touch or you know a friend who does, don’t wait for the perfect moment. Set up a recurring one.
Regular rituals take the pressure off vulnerability. A monthly lunch, a standing game night, even shared fandom over a sports team can become your bridge back to connection.
“It doesn’t have to be deep to be meaningful,” Damona shares. “You’re just giving the friendship a place to live.”
Even one standing plan can shift how connected you feel and how safe it becomes to say more next time.
(20:00) The New Friendship Playbook
Connection isn’t gendered. And real friendship doesn’t come from grand gestures. It comes from small acts of courage over time.
So if you’ve been telling yourself you can’t say how you feel, or you’re too old to make new friends, or it’s too awkward to reach out, here’s your reframe:
You can. You’re not. And it isn’t.
Try something this week. Make a list of people you’d like to reconnect with. Or notice the folks you cross paths with regularly and take the first step. Ask a question. Make a comment. Be curious.
Sometimes all it takes is a little reminder that you matter to someone and that they matter to you.
💌 Got a communication question you’ve been sitting on?
Whether it’s about dating, relationships, boundaries, or what the heck to text back… Damona’s 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, and you.
📝 Want a better way to track what’s working (and what’s not) in your love life?
Get your free Date Tracker at damonahoffman.com/datetracker
The Big Confession & Texting Gremlins
“I Think I Found My Wife”… After One Date?
Does this mean it’s over? Did he mess it up forever? Is there still a chance?
This week on Dates & Mates, we explored what happens when an incredible first date leads to a connection so strong that you forget to pace yourself. You know the feeling: sparks fly, emotions swirl, and suddenly you’re saying the one thing you know you shouldn’t.
A listener wrote in:
“Late at night, I had to get these thoughts off my mind. I told her I felt like I’d found my wife. She expressed that she was disappointed that I would say this after what she told me about moving too fast and that it was best we not see each other.”
So what now? Is there a way back after scaring someone off, or is this one of those live and learn moments?
(02:00) The Danger of Declaring Too Much, Too Soon
Big feelings aren’t bad, but unprocessed feelings shared too early can be overwhelming. Just because you feel something intense doesn’t mean you need to say it right away, especially when someone has already told you their boundaries.
If you’re feeling the urge to overshare early, pause and ask yourself: Is this about connection, or is it about control?
When we lead with big declarations, we sometimes bypass the slow-building safety that real intimacy needs.
One of the most powerful takeaways? Your desire for connection is valid. But your delivery matters.
(04:00) The “Fairy Tale Filter” That Blurs Our Judgment
When something feels magical, our brains love to fill in the gaps, especially when there are only a few data points.
That electric first date? It can start to look like a movie montage in your mind, complete with a happily ever after.
“You’re leaning into the fairytale, my friend,” Damona shared. “Our brains love stories. When we don’t have all the information, we start to fill in the blanks.”
This is where self-awareness matters. When you catch yourself romanticizing someone after a single date, slow down and reflect: What do I actually know about them? Noticing your projections can save you from disappointment and help you stay present with what’s real.
(07:00) Why You Felt That Deep Connection And What It Really Meant
Here’s a reframe: maybe what you felt wasn’t about her at all. Maybe it was about you showing up as your most open, grounded self, possibly for the first time in a long time. That kind of presence can make anything feel profound.
If you’re wondering why a date felt different, look at how you showed up. Were you less guarded? More present? Less worried about outcomes? That’s worth celebrating, and replicating, no matter where things go with that particular person.
That deep feeling you’re chasing? It might not be about finding her. It might be about finding you.
(13:00) When You Know Someone’s Trigger… and Walk Right Into It
This listener’s date shared a clear vulnerability: she’d been hurt before by someone who moved too fast. And then he did the exact thing she was afraid of.
Missteps like this don’t make you a bad person; they make you human. But learning to listen beneath someone’s words for the emotional need behind them? That’s a game-changer.
If someone tells you what overwhelmed them in the past, treat that as a roadmap not a challenge. Respecting boundaries builds trust. Overriding them, even with the best intentions, usually backfires.
(18:00) Can You Recover From Coming On Too Strong?
Yes… but only if you do it with honesty and care. Start by owning the impact, not just the intention.
Say something like: “I really heard you when you said you needed to take things slow, and I blew right past that. I let my emotions lead, and I get why that didn’t feel safe. If you’re open to it, I’d love to start over. No pressure, just presence.”
Repairing trust isn’t about chasing. It’s about showing emotional maturity and consistency, not romantic grand gestures. If someone chooses to re-engage, let it be on their terms. And if they don’t? Take the lesson forward.
💭 Got a tricky convo, awkward moment, or mixed signal you need help decoding? You’re not the only one.
Whether it’s a confusing text thread, a situationship that’s getting murky, or a relationship rule you’re rethinking… bring it to Dates & Mates.
Damona’s here to help.
Drop 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 be featured in a future Dear Damona segment, and yes, you can stay anonymous.
Oh, and one more thing: this show isn’t just about dating anymore. It’s about all the relationships that matter most, because love shows up in more ways than one.
📝 Want a better way to track what’s working (and what’s not) in your love life?
Get your free Date Tracker at damonahoffman.com/datetracker
Love After Loss & The Vulnerability Gap
This week’s episode touches a place many of us don’t talk about enough: what it feels like to start over emotionally after loss.
Even when a connection seems strong on the surface, it’s not always easy to tell whether it’s built on real compatibility or just mutual comfort. And when grief is part of both people’s past, the lines between healing and hoping can get blurry.
This week, a listener shares:
“My partner and I both lost our spouses, and we bonded over that. Now, three months in, I’m the one opening up and being vulnerable. He also wants us to move in together already. Am I asking too much? Or moving too fast?”
She’s asking a question that goes deeper than just timelines or teasing. It’s about what it really means to feel emotionally safe, and what to do when that safety isn’t mutual yet.
(3:00) Grief Bonds Are Real, but So Are Emotional Timelines
When someone has gone through something similar to you, it creates instant understanding. But emotional readiness doesn’t always travel at the same speed.
Just because someone relates to your story doesn’t mean they’re in the same chapter of healing.
If your emotional needs are showing up early in a relationship, and the other person isn’t matching that energy, it’s worth pausing to ask what you actually need now… not what you both needed back then.
The grief might have brought you together, but connection takes more than shared history.
(7:45) When One Person Opens Up and the Other Stays Quiet
The listener feels like she’s carrying the emotional weight in the relationship. This isn’t uncommon, especially when two people are still figuring out their own way forward after loss.
The tricky part is that vulnerability doesn’t always look the same. Some people speak in full paragraphs. Others shut down or use humor.
But if you’re consistently feeling dismissed, like your feelings don’t have a place to land, something needs to shift.
As Damona puts it, “It’s not that your partner isn’t feeling something. It’s that he may not have the language or emotional tools to express it the same way you do.”
You can’t force someone to open up, but you can stop over-functioning in the emotional space and see what happens when you leave room for them to step in.
(15:00) Language That Makes You Feel Small Isn’t Just a Joke
“He says I’m crazy, but he likes crazy.” It sounds playful, maybe even affectionate. But if you flinch when you hear it, or feel smaller afterward, that’s a sign to pay attention to.
Teasing can sometimes be a stand-in for intimacy. It keeps things light instead of real. If your emotional expression is being met with sarcasm or labels, even in jest, it chips away at your confidence.
Damona says, “If it doesn’t feel like a joke to you, then it’s not a joke.” Trust your gut. The language you allow becomes part of the relationship’s tone.
(20:10) Fast Moves Might Be Covering Emotional Gaps
Three months in, and the idea of moving in together is already on the table.
It might sound romantic, especially when two people feel close. But big steps too soon can sometimes be a distraction from deeper emotional work that hasn’t happened yet.
Ask yourself: Are we aligned in how we handle conflict? Do we feel emotionally steady day to day? Has there been real space for disagreement, or are we coasting on shared comfort?
Moving in isn’t a test of commitment. It’s a magnifier. If something feels off now, it won’t disappear in close quarters. It usually gets louder.
(22:40) Creating Emotional Safety Without Overexplaining
When your partner isn’t opening up, it’s easy to fall into the trap of explaining your needs over and over. But vulnerability is a two-way exchange. You’re not just trying to be heard, you’re trying to feel joined.
Instead of pushing for them to say more, try modeling the kind of connection you want. Share something personal without a big lead-in.
Name a small gesture they did that made you feel seen. Keep it light, but specific. Emotional connection doesn’t always start with a heavy talk. Sometimes it begins in the quiet moments where safety is built, not demanded.
Damona shares, “You’re not asking them to be someone else. You’re showing them how to be more of themselves, out loud, and with you.”
💌 Before you go, if you’re stuck over what to text back, spiraling over mixed signals, or just navigating something messy in love (or friendship, or family), don’t sit with it alone.
Damona’s here to help.
Slide into our DMs on Instagram, TikTok, or Facebook, or text/leave a voicemail at 424-246-6255. Your question could be featured in an upcoming Dear Damona segment, and let’s be real, if you’re wondering about it, someone else probably is too.
Oh, and one more thing: this show isn’t just about dating anymore. It’s about all the relationships that matter most, because love shows up in more ways than one.
📝 Want a better way to track what’s working (and what’s not) in your love life?
Get your free Date Tracker at damonahoffman.com/datetracker
The Friendship Drift & Support Squads
Friendship drift is real, but it does not have to be the end of the story.
Have you ever felt your best friend slowly drifting away, not in a big, dramatic blowup, but in small, almost imperceptible ways?
You still talk regularly, but the conversations that used to go late into the night are now quick updates about work, weekend plans, or the latest Netflix binge. And when you try to open up about something deeper, the subject changes.
This week on Dates & Mates, we unpack a listener’s question:
“We’ve been best friends for years, but lately it feels like we’re only talking about surface-level stuff. Is this just what happens as we grow up?”
We explore why friendships shift over time, the mistakes we make when trying to “fix” them, and simple, low-pressure strategies to bring back connection without guilt trips or awkward energy.
We also share how to build a wider support system and offer tips that can strengthen all your relationships, from friendships to family ties to even your dating life.
(1:52) It’s Only Weird If We Make It Weird
When something feels “off” in a friendship, our first instinct is often to avoid it.
But awkwardness usually comes from resisting change, resisting the unknown, resisting showing up fully as ourselves.
As Damona says, “A lot of that weirdness actually comes from resistance… and I encourage you to lean into it… mindfully.”
We break down how small shifts in your own approach can ease tension and open the door for more authentic conversations.
(6:10) The Third Character in Every Friendship
There’s you, there’s your friend, and there’s the friendship itself… a “third character” with its own needs.
Life changes like marriage, kids, new jobs, or caregiving can pull focus and naturally shift priorities.
When we see the friendship as something we both actively nurture, it’s easier to adapt instead of falling into resentment. This perspective also helps you spot whether the friendship simply needs a different kind of attention right now, rather than a total overhaul.
(18:33) Reopening the Door to Connection
Sometimes when a friend doesn’t respond to our deeper shares, it’s not about us; it could be timing, emotional bandwidth, or comfort level. That’s why how you try to reconnect matters.
We share ways to re-engage without forcing it, like using shared memories or parallel experiences as conversation starters.
As Damona explains, “Storytelling can remind someone of your safety and security, without it feeling like a vulnerability test.” These small, low-stakes moments can be powerful in reestablishing trust.
(36:20) Diversify Your Emotional Support
Not every friend can meet every need and that’s okay. Building a broad emotional support network ensures you’re not relying on one person for everything.
When you have different friends for different roles, the confidant, the workout buddy, the travel partner, you can appreciate each relationship for what it brings instead of trying to make it be everything.
That mindset shift alone can reduce pressure and keep connections feeling light, natural, and mutually fulfilling.
💌Have a communication conundrum? Damona’s got you.
Whether it’s love, conflict, or just figuring out what to text back, no question is too big or too small.
Submit your dating, relationship, or communication 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!
And don’t forget — Dates & Mates is now about all your significant relationships, not just romantic ones.
📝 Want a better way to track what’s working (and what’s not) in your love life?
Get your free Date Tracker at damonahoffman.com/datetracker
Boundaries, Moms, & The Post-Date Spiral
When Your Mom’s Opinions Are Tanking Your Dating Confidence
We take on all types of relationships on this show, including romantic, friendship, and even work, but this week, we’re zooming in on one that hits home for a lot of us: the one with mom.
This week’s question came from a listener who’s close with her mother. Maybe too close.
She wrote: “She wants me to be happy, but it’s gotten to the point where I second-guess my own instincts.”
Sound familiar?
Whether it’s about who you date, how you show up, or what kind of love you “should” be chasing, sometimes the people who love us most can leave us doubting ourselves the most.
This episode is about creating space to breathe, to choose, and to lead with your own voice, without cutting off the people you care about most.
(1:28) When Love Sounds a Lot Like Control
It can be hard to tell when your mom’s love crosses into overstep until you realize her voice is louder than your own.
One minute you’re glowing after a great date, and the next, you’re spiraling because of a throwaway comment she made about your type, your outfit, or the way you told the story.
We share why even the most loving advice can feel like control and how to spot when it’s chipping away at your confidence.
As Damona says, “She already did the programming. Now it’s hands off.” Because when your dating decisions start to feel like a family group project, something’s gotta give.
(5:42) Boundaries That Don’t Burn Bridges
It’s possible to love your mom deeply and still need her to back off.
When her opinions start to override your own, it’s time for some emotional guardrails that protect your peace without blowing up the relationship.
Damona shares how to set expectations before things escalate, including one simple strategy that shifts the tone entirely: “You have an absolute responsibility to advocate for yourself. Maybe along the way, you educate your mom on how to support you.”
If you’ve ever felt guilty for pulling back or struggled to hold the line without losing your cool, this is the kind of script you’ll want in your back pocket.
(12:07) Stop Calling Mom Before the Date
You’re not just picking your outfit, you’re picking your mindset. And the people you let in before a date can make or break the energy you bring to the table.
We get into the idea of “mindset movers” and why calling your mom (or anyone whose vibe throws you off) right before a date is a setup for self-sabotage.
You’re building a rhythm and rituals for dating, one that starts with your voice, not someone else’s fears.
(21:15) Before the World Gets a Vote
What you do after a date is just as important as how the date went.
The opinions, the second-guessing, the noise, they all show up fast. But if you can catch your own thoughts first, you get to decide what the story really was.
We talk about how to hold onto your perspective with simple post-date rituals like journaling or using our free Date Tracker.
As Damona puts it, “You want to remember how you felt in that moment, before anyone else’s opinion reshapes your memory.”
GET THE FREE DATE TRACKER HERE
(30:55) Just Because She Asks Doesn’t Mean You Have to Answer
There’s a difference between being honest and handing over every detail before it’s ready.
In early dating, emotional privacy isn’t secrecy; it’s self-protection. Oversharing can feel like bonding, but it can also open the door to opinions that shake your confidence or steer you off course
This part of the episode walks through how to decide what to share, when to share it, and why keeping some details to yourself might be the most loving move—for both of you.
It’s not about keeping secrets. It’s about protecting something sacred while it’s still taking sha
💌Have a communication conundrum? Damona’s got you.
Whether it’s love, conflict, or just figuring out what to text back, no question is too big or too small.
Submit your dating, relationship, or communication 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!
And don’t forget — Dates & Mates is now about all your significant relationships, not just romantic ones.
📝 Want a better way to track what’s working (and what’s not) in your love life?
Get your free Date Tracker at damonahoffman.com/datetracker
Feminine Energy Fatigue & The Myth of Being Chosen
Have you ever been told you need to be “softer” to be loved?
Or felt like you had to shrink parts of yourself to fit into someone else’s idea of what a woman “should” be? You’re not alone.
This week on Dates & Mates, we dedicate the entire episode to a listener question that is at the heart of modern gender dynamics in dating.
Esther left us a voice memo asking: How can I be a strong woman who supports a partner without losing myself? And how do I get into my feminine energy on a date?
There’s a lot to unpack. And that’s exactly what we do in this episode.
(2:00) Can You “Build Up” a Man, and Should You?
We start with a powerful question about the role women are often expected to play in their relationships.
Esther wants to know how to be a strong woman who helps build up her man. Is that really your job? Or are we just repeating old patterns handed down through outdated relationship narratives?
Damona says, “That’s his work. That’s not your work. It’s not your job to make your partner feel any kind of way other than safe and cared for.”
It’s a reminder that real support doesn’t mean sacrificing your own needs.
(6:00) Encouragement > Fixing
Let’s talk about one of the most common traps we fall into when trying to support a partner: trying to fix them.
How can you shift from correction mode into true encouragement? Maybe the better question is why this change makes all the difference in how secure and seen your partner feels.
We also look at how over-correcting in relationships can erode trust and create imbalance.
(9:00) Vulnerability Is a Superpower
Especially for men, showing emotion has often been misunderstood as weakness.
But we explain why emotional openness is actually one of the strongest things we can bring into a relationship.
We dig into what emotional safety looks like and why so many people struggle to create it. You’ll come away thinking differently about how vulnerability works in healthy love, and how to invite it in.
(12:00) Feminine Energy Isn’t a Costume
Esther’s second question? How to get into her feminine energy around men.
“If you’ve been telling yourself, ‘I just need to get more into my feminine energy so I can attract the right man,’ I gently want to challenge that,” Damona says. “Because here’s the truth: feminine energy is fake…it’s a label”
Are we talking about being agreeable? Submissive? Passive? Let’s challenge the idea that “feminine energy” is something you need to switch on to be desirable, and instead ask, what if it’s just about feeling safe enough to receive?
(16:00) The Risk of Performing for Love
Trying to mold yourself into someone else’s ideal, even subtly, always comes at a cost.
Let’s talk about the danger of trying to “act feminine” in a way that doesn’t feel authentic. What does it cost you to pretend you don’t have preferences? To mute your voice? To play small?
You need to get real about what performance in dating looks like and how letting it go might be your path to true connection.
(19:00) Strength Isn’t a Problem — It’s the Point
Esther asked how to be strong and still be cherished.
The answer isn’t to soften yourself into someone else’s comfort zone, it’s to be whole. Damona shares why the right partner won’t just tolerate your strength, they’ll value it.
This episode is a celebration of the full you…the ambitious you, the assertive you, the emotional you. Because strength isn’t something to hide, it’s something to bring boldly into your relationships.
💌Have a communication conundrum? Damona’s got you.
Whether it’s love, conflict, or just figuring out what to text back, no question is too big or too small. Submit your dating, relationship, or communication 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!
And don’t forget — Dates & Mates is now about all your significant relationships, not just romantic ones.