Is Financial Compatibility a Deal Breaker?

Have you ever met someone who feels perfect on every emotional level? Do you find yourself wondering if caring about financial stability makes you shallow?

In honor of Halloween, when many of us share dating horror stories, we’re talking about what so many find super scary in relationships: money.

We’ve been told our whole lives that love should transcend material things, that if the connection is real, the rest will just figure itself out. But here’s what happens in real life after over 15 years of coaching: financial compatibility isn’t about being materialistic or gold digging. 

It’s about life stage, shared values, and whether two people are actually positioned to build something together.

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

She shared:

“I met a wonderful man online. I’m 50 and he’s 46. We went on two amazing dates. He’s attentive, attractive, and dare I say we had a magical connection. Here’s the thing: it seems he’s going through a major life transition. He quit his tech job nine months ago and has been figuring it out. His phone only works on Wi-Fi and he might need to figure out a different living situation to cut costs. I’ve worked really hard to get to where I’m at today. I’d like someone who could meet me halfway. Is this a deal breaker?”

This is a question that goes deeper than money: can I make this work if I lower my standards a little bit?

(4:00) You Already Know the Answer

When you start by listing all the amazing things first, the chemistry, the laughter, the magical feeling, that’s telling. All of that matters.

But if you’re already questioning it after just two dates? That matters even more.

When someone is truly right for you, you’re not lying awake wondering if you’re being too picky. You’re excited. You feel secure.

The fact that you’re asking if someone’s financial situation is a deal breaker tells you everything you need to know.

(5:00) Transition vs. Just Stuck

Here’s the difference: a transition has momentum. It has milestones. It has forward motion.

Someone who’s been coasting for nine months looks like this:

• No stable housing
• No phone plan
• No clear path forward

That’s not reinventing yourself. That’s survival mode.

Do you want to date someone in survival mode when you’re looking for a life partner? At 46, this might be a pattern. And if it is, you’ll end up subsidizing their lifestyle while they “figure it out.”

You deserve somebody ready to build with you, not somebody you have to build up first.

(10:00) When the Math Doesn’t Math

A 46-year-old former tech worker who can’t afford a phone plan or stable housing? Something doesn’t add up.

Questions worth asking:

• Did they quit or get fired?
• Is there an addiction problem?
• Are they lying about how long this has been going on?
• Are they hiding another life or family?

This is where digital detective work matters. Check LinkedIn. Do a reverse image search. Use PeopleFinders to verify their story lines up with reality.

It’s not paranoia. It’s protecting yourself when details don’t quite match.

(14:00) What “Meeting Halfway” Really Means

Wanting someone who can meet you halfway sounds reasonable. But if they’re not even meeting you a quarter of the way, who’s closing that gap?

Meeting halfway doesn’t mean matching income dollar-for-dollar. It means having a partner who’s a contributor, not a project.

When someone can’t pay for a working phone and plans walk dates that cost nothing (not even a coffee), and they’re comfortable with that?

You need someone additive to your life, not a constant drain.

(17:00) Resentment Will Kill the Magic

If you move forward by lowering your standards, you might not resent them today. Maybe not next month.

But eventually you will.

You’ll resent always planning. Always paying. Always sacrificing. And that resentment will destroy whatever connection you had.

There’s this narrative that women should be understanding, see potential, be patient. But wanting someone who can contribute isn’t shallow. It’s practical, self-respecting, and fair.

When you’ve worked hard to build your life, you deserve someone who’s done the same. Someone who walks beside you, not someone you have to carry.

That’s not asking too much. That’s the bare minimum.

Knowing what you won’t settle for is just as important as knowing what you want.

When you’re clear on your non-negotiables, you create space for the right people to show up.

💌 Got a relationship or question you’ve been sitting on?

Whether it’s about dating, relationships, boundaries, or what the heck to text back, 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 felt your heart sink when a text conversation goes sideways?

Do you find yourself staring at your screen, trying to decode what someone really meant, wondering if a simple phone call could have prevented the whole mess?

The truth is, how we communicate has fundamentally changed, and most of us are still figuring out how to navigate it. 

Text-based communication has become our default, but it’s stripping away the context, tone, and connection that make real understanding possible. 

And when you’re trying to build something meaningful with someone who communicates completely differently than you do? It doesn’t just create frustration. It creates distance, which our listener, Angie, learned the hard way:

“I’m seeing this guy and we have totally different ways of communicating and it’s starting to become a problem. He’s all about texting, like everything is through text with him. He wants to have these deep conversations over text and I’m more of a ‘can we just call, can we actually talk?’ person. Last week I had something I really needed to bring up with him and I texted him about it since that’s what he prefers and it went so wrong. Do you think different communication styles can actually work, or am I just fighting a losing battle here?”

If you’ve ever compromised how you naturally communicate to accommodate someone else, only to watch it backfire, you’re not alone. And no, this isn’t necessarily a sign you’re incompatible. But it is a sign that something needs to shift.

(2:00) The Texting Trap Is Real

Here’s something that might surprise you: texting has disrupted relationships MORE than dating apps ever did. Everyone loves to blame swiping for why we can’t connect anymore.

But the real problem? 

• 70% of our communication today happens through typed words, and our brains literally haven’t caught up. We’re all walking around confused and frustrated because of it.

When you communicate over text, it strips away all of the context that we learned in how to communicate when we were younger.

If you didn’t grow up glued to a phone, learning to communicate through text feels like trying to speak a language you never studied. And even if you did grow up texting, it still can’t capture tone, facial expressions, or those crucial pauses that tell you what someone actually means.

We’re not mad that texting exists. We’re mad because we keep trying to have serious, vulnerable conversations through screens the size of our palms, then wonder why we keep misunderstanding each other.

(9:00) Why They Love Texting (And It’s Not What You Think)

Before you decide someone’s texting habit is a red flag, get curious about what’s actually going on.

Some people text because they need time to think. Real-time conversation feels like getting ambushed. They’re worried they’ll say something wrong, and their brain works slower than their mouth needs to move.

Other reasons someone might prefer texting:

• It feels safer – Especially for introverts. Texting provides a buffer of intimacy in digital communication to help them access their feelings more.
• It’s about efficiency – Maybe they have a lot of pressures at work and can’t process everything right now. Texting lets them do it on their own time.
• They’re avoiding something – Maybe they’re avoiding vulnerability that will come out in a real-time conversation. They don’t have to sit with uncomfortable silence, see your immediate reaction, or be fully present in the moment.

Figuring out why someone prefers texting doesn’t mean you just have to live with it forever. But it does help you understand what you’re actually working with.

(14:00) The Compatibility vs. Concession Question

Communication style matters. Like, really matters. But it’s not automatically a dealbreaker if you’re both willing to adjust.

Here’s where people panic: they hit one bump and immediately think, “This is it. We’re not compatible. It’s over.” But what if this friction is actually useful?

Compatibility is not about being the same. It’s about being able to bridge the gap.

Real compatibility means both people can flex. But here’s what actually matters: if you’re the only one bending, that’s not compatibility. That’s you making all the sacrifices while they stay comfortable. And that builds resentment faster than you think.

The questions to ask:

• Is your partner willing to stretch the way you’re stretching for them?
• Have they even been given the opportunity to do that?

Because in this case, there was texting when calling was needed. The question is, would they call when you needed to talk on the phone?

(18:00) How to Have “The Talk” About Talking

You can’t fix this by yourself. You need to actually talk about how you’re going to talk going forward.

And yeah, this conversation needs to happen in person —not as punishment, not as some power move —but because it’s too important to risk screwing up again.

Here’s the framework:

• Start by setting the stage: Give him a heads-up that you need to talk without blindsiding him or making him dread the conversation.
• Then name what happened: Acknowledge what went wrong, validate his preference, then ask how you can meet in the middle.
• And then pause: See how he responds—does he get defensive, dismiss your needs, or actually hear you and try to find a solution?
  

Give them space to respond before you jump in with solutions. 

Maybe you’ll find out your calls wreck their work flow. Maybe they just need time to process before they talk. You won’t know until you ask.

(24:00) Finding Your Communication Code

This isn’t a wall. It’s a door you both need to figure out how to open.

Think about all of these skills as life skills that you can then take into your next relationship or your work.

Two-person problem, two-person solution. You figure it out together. Can different communication styles work? Sure. But only if you’re both willing to move.

If they care about you and this relationship, they will meet you halfway or three-quarters of the way, or a quarter of the way, or just somewhere along the road.

And if they won’t budge? Then you’re not losing anything. You’re learning who they are and whether that actually fits your life. 

The point isn’t to change each other. It’s to find a way to connect that doesn’t require either of you to disappear.

Communication problems don’t mean you picked the wrong person. 

They mean you have a chance to build something that actually works. If you’re both willing to listen, adjust, and care about what the other person needs, you’re not stuck. You’re learning how to love someone in a way that’s real. And that matters.

💌 Got a communication question you’ve been sitting on?
Whether it’s about dating, relationships, boundaries, or what the heck to text back, 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, 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

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.

 

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

 

“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

 

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