It’s January, which means a lot of folks are thinking about fresh starts, new goals, and healing past heartbreaks If you’ve recently ended a relationship or  the Valentine’s Day countdown is spiking your dating anxiety, you’re not alone.

Something’s happening in dating lately. Something under the surface that’s getting in the way of communication, connection, and every important relationship in our lives. 

And this is two things: the stories we tell ourselves and the patterns we keep repeating.

This week, Sabrina Zohar, entrepreneur and host of the Sabrina Zohar Show, joined the Dates & Mates podcast to unpack how to process endings without self-blame, understand dating anxiety, and break the patterns that keep showing up in your love life.

The start of a new year is the perfect time to reset. But that only works when you’re honest with yourself about what you’re ready for, who you want to be with, and who you really are.

(03:00) Meet the Creator Breaking Down Dating Patterns

Sabrina Zohar is an entrepreneur and host of the Sabrina Zohar Show, a podcast that ranks in the top 0.05% globally.

She’s built a following by calling out the patterns we can’t see in ourselves. The texting traps. The attachment style weaponizing. The ways we turn partners into projects instead of people.

Her own story? She lost her business dream when Shark Tank sent her home moments before her big break, her dog Clem passed away suddenly, and she ended a relationship all in the same month. Five days after the breakup, she met her current partner, Ryan.

But only because she’d finally learned to choose herself first.

(05:00) The Five-Minute Grief Practice That Actually Works

Sometimes the breakdown is the breakthrough.

When Sabrina hit rock bottom, she did something counterintuitive: she set a timer for five minutes and allowed herself to be sad. Not productive sad. Not journaling-through-it sad. Just sad.

That permission to grieve without fixing it released her from ruminating. She wasn’t stuck in “why didn’t it work?” She felt it, validated it, and moved forward.

What changed when she met her partner five days later:

• She went on the date to enjoy herself, not to be chosen
• She was honest about what she wanted upfront
• She wasn’t afraid to lose him because she was more afraid to lose herself

Ryan called her back. His reason why reveals everything about dating from self-trust instead of scarcity.

(14:00) Your Phone Is a Dopamine Slot Machine

The reality: Dating anxiety is at an all-time high. Three hours without a text sends people spiraling.

Sabrina breaks down why this is happening. Technology turned dating into constant availability. We’re interpreting tonality through screens. Response time became a measure of interest.

But here’s the generational insight that explains everything:

Gen Xers and Millennials grew up with disappointment built into the game. You died in Mario, you lost. You waited your turn. Gen Z grew up with games that never end, instant downloads, no waiting for anything.

That shows up in dating as an inability to sit with uncertainty.

The episode unpacks how to tell if you’re in your adult brain or your child brain when the texting anxiety hits.

(18:00) When Urgency Means You’re Dating from Your Wounds

Damona shares her own pattern: as a casting director, she kept attracting unavailable or at times manipulative actors and musicians. Handsome, charismatic, exciting. Also shallow.

She had to reframe what attractive meant. Not the chaos. The consistency.

Sabrina’s framework for recognizing when you’re dating from wounds instead of wholeness:

• Notice when urgency shows up: I need to know NOW
• Ask yourself: How old do I feel right now?
• Check: Is this my adult brain or the part of me that needed constant reassurance as a kid?

If it feels like a teenager talking about the cute boy in class? You’re in your child brain. The episode walks through how to parent yourself through it.

It takes 3,000 repetitions to rewire a thought pattern. Let today be number 2,999.

(23:00) Hurting vs. Harming: The People Pleaser Test

Someone asks: “I went on three dates but I don’t want to see them again. How do I say this without being a bitch?”

Sabrina’s reframe: Are you hurting them or harming them?

Hurting someone’s feelings is okay. You can hurt feelings by saying no. What’s harmful? Wasting their time. Keeping them in something you know isn’t going anywhere.

Especially when the biological clock is ticking.

The conversation shifts to what’s actually in your control when you want kids but you’re single in your 30s or 40s. Sabrina shares a story about a friend who got pregnant at 43 from a one-night stand after being told she’d never conceive.

Why she kept the baby reveals everything about making choices that honor your priorities over your fears.

(31:00) What Was My Part in This?

After a breakup, we want to blame everything on them. But you can’t help someone stuck in victim mode.

Sabrina’s question that breaks the pattern: What was my part in this?

Not to shame yourself. To take ownership. To extract the lesson.

The episode walks through the follow-up questions that help you see what you’ve been avoiding. Why acknowledging the truth is the scariest part. Why once you see it, you can’t unsee it.

And why that’s exactly when you finally get to choose yourself.

(36:00) Stop the Attachment Style Charity Work

It’s time we reckon with the anxious-avoidant narrative that turns your partner into a project.

Both attachment styles are insecure. You’re not superior because you’re anxious and self-aware. You’re both dealing with fear in different ways.

One of Sabrina’s followers asked a question about a guy being “inconsistent” after two dates. What she meant: he takes a few hours to respond to texts.

The reality: He works the graveyard shift. He’d already made plans for a third date. He communicates. He’s interested.

But she nearly walked away over response time.

When it’s actually a red flag:

• They’re rude or disrespectful
• They’re not reciprocal
• They’re not intentional

When it’s just texting anxiety:

• They didn’t respond for a few hours because they have a life

The patterns that kept you stuck don’t have to follow you into 2026.

Whether you’re healing from a breakup, stepping back into dating, or trying to break the texting anxiety loop, the gift you give yourself is clarity. Even when it’s uncomfortable. Especially when it’s uncomfortable.

💌 Got a breakup question? Dealing with dating anxiety? Trying to figure out if you’re hurting or harming someone by staying?

Whether it’s about processing a painful ending, recognizing your patterns, setting boundaries without guilt, or navigating modern dating without losing yourself, 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 covers all the relationships that matter in your life—romantic partners, exes you’re still processing, friends, family, and most importantly, 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

 

If you’re tired of the maybes, the breadcrumbs, and unclear intentions, you’re not alone.

There’s that feeling when navigating dating and everything feels fuzzy. Everyone’s tiptoeing around what they actually want, and you’re left decoding emoji reactions instead of having real conversations. After 12+ years of watching relationship patterns shift, one thing is clear: that era is ending.

The last few years have been defined by dating ambiguity. Lots of emotional labor. Very little payoff. But something’s shifting. Singles are done negotiating with “maybe.” The move from vague possibility into intentional choice is happening right now, and it changes everything.

This is about clarity replacing casual, about effort becoming the baseline, and about whether you’re ready to stop waiting for people to show up differently than they already have.

Dating predictions for 2026 and beyond aren’t guesses. They’re based on data, trends, and what’s showing up in how singles are approaching relationships right now. And if you’re wondering what this means for you, pay attention. This could be the year you stop settling for potential.

Here’s what’s coming.

(01:00) Clear-Coding: The End of Dating Guessing Games

For the first time, singles are openly declaring their intentions from the start. No more waiting three dates to ask what this is.

Clear-coding, as Tinder’s Year In Swipe report calls it, is replacing emotional labor with clarity. Finally getting the answer to the question you’ve been afraid to ask. People are saying upfront: I’m looking for a serious relationship, a casual connection, or something in between.

What this means:

• Clarity happens faster (or at least, it should)
• Some people will still ghost before they answer
• But when someone does answer, you know where you stand
• Fewer wasted months on someone who was never available for what you actually need

The downstream effect? Faster alignment. Faster exits. And the ability to invest your energy where it’s actually reciprocated.

(05:00) Kindness as the Baseline, Not the Exception

Tinder data shows that 54% of singles say kindness is their top value. Here’s the challenge:

If you’ve put kindness on your ideal partner list or your vision board, are you actually walking away when you don’t see it?

A lot of people tolerate cruelty, from others and from themselves, by accepting substandard behavior from people they really want to work out. Kindness matters until it doesn’t. Until potential or history or fear of being alone makes an exception worth it.

In 2026, kindness stops being optional. It’s the minimum.

If someone isn’t treating you with basic kindness, the answer is simple: thank you, next. Not “let me try harder to earn their kindness.” Not “maybe they’ll grow.” Just clarity that this person isn’t aligned with what was said matters.

Before meeting someone, there was Operation DNG: Operation Date Nice Guys. (And I mean nice in the actual sense, not internet nice guy sense.) That one decision completely changed the trajectory. Because when you’re serious about kindness, you stop wasting time on people who aren’t.

(08:00) Hot Take Dating: Own Your Opinions

Here’s what’s shifting in attraction: opinions matter now.

41% of singles say they wouldn’t date someone with opposite political views. That’s a massive shift from the “don’t discuss politics on a first date” era. Now, people are leading with their values, their beliefs, their actual hot takes. And they’re not apologizing for it.

The old rule was silence or strategy: don’t offend, don’t overshare, keep it neutral until you’re sure they like you. But that creates a false version of connection. Performing, not relating.

Here’s what 2026 demands instead:

1. Figure out what you actually believe. Not what you’ve been told to believe or what sounds good—what do you actually think?
2. Say the thing. Lead with your real perspective. If dating is hard, controversial beliefs make it harder in the short term. They also make it shorter for people who aren’t aligned with you.
3. Watch who responds with curiosity instead of judgment. That’s your person.

If you’ve been shrinking your real opinions to fit someone else’s comfort level, your authenticity isn’t a liability. It’s a filter.

(13:00) The Dinner Date Revival (And What It Signals)

This is a shift worth noting.

The advice used to be: keep first dates short. Drinks. An hour, maybe ninety minutes. Light and bright. That’s all you need.

But 2026 is different. Dinner dates are coming back, and they’re signaling something important: buy-in.

When someone invests two hours and actual money, they’re showing up differently. They’re not a looky-loo. They’re someone ready to be present. Dinner dates also cut through all the texting chaos. You can’t hide behind messaging when you’re sitting across from someone for two hours. You get to see effort, presence, and whether they actually want to know you or just like the idea of you.

What dinner signals:

• They planned ahead
• They’re willing to invest time
• They’re serious about being present (not half-listening while scrolling)
• You have nowhere to hide—and neither do they

(17:00) Interest vs. Intention: Stop Mistaking Words for Plans

This is the one that will save months of wasted energy.

Interest feels good. Someone texts you’re amazing. “We should definitely hang out.” It feels like something. You feel seen. You feel wanted. That’s a nice feeling, so you hold onto it.

But intention? Intention shows up with specifics. “Are you free Saturday or Wednesday? I’d like to take you to dinner at XYZ.” One is a feeling. The other is a plan.

Here’s the difference:

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

Intention = “I’m free Wednesday at 7. There’s a new Italian place I want to check out. Does that work?”

One lives in possibility. The other lives in action. And in 2026, confusing the two is over.

Watch what people actually do, not what they say. If someone disappears the second you ask for concrete plans, that’s the answer. You’re not asking for too much. You’re protecting your time and your hope, and that’s what actually matters.

(20:00) Effort Becomes the Minimum

This is the shift that changes everything.

Consistency is going to outweigh potential.

It’s over waiting for people to eventually show up. The goal is to see it now. Early stage investment in a relationship—showing interest right away, making actual plans, staying engaged—is now the baseline expectation. No more “let me see if they step up after a few more dates.”

Here’s what A-for-effort looks like:

• They text back within a reasonable timeframe
• They make specific plans, not vague ones
• They follow through on what they say
• They show genuine curiosity about you

And that applies to everyone in the dynamic. If you’re putting effort in, they have to match it. If they don’t, boundaries do the work that hope’s been trying to do.

It’s “A for effort or it’s nothing.” No middle ground. No “let me wait and see if they step up.” Either they’re showing up or you’re moving on.

(22:00) The Texting Trap Has to End

Something’s been created that feels like intimacy but isn’t: endless messaging.

Message for weeks. Build up expectations. Have these long text threads at night. Feel like you know this person. Then you meet them and wonder: who is this?

That’s because it’s a false sense of intimacy.

The reality of texting:

• It’s at least 50% fakery and posturing. You have time to craft your responses. You edit. You delete. You’re performing.
• You’re not actually screening anything important. You’re screening for banter, for witty comebacks, for the ability to text well. That has nothing to do with whether you’re compatible in real life.
• You’re trapped in the “texting trap” without realizing it. You’re exhausted, overwhelmed, and anxious from managing multiple conversations that go nowhere.

This year, break that pattern.

Move the conversation to an actual date faster. Maybe it’s a video call to pre-screen. Maybe it’s fewer messages before saying, “Let’s grab coffee and see if we actually vibe in person.” The goal is clear: get off the phone and into real life. That’s where real connection happens.

(25:00) Ghosting Gets Called Out

Ghosting is at an all-time high because accountability is missing.

It’s uncomfortable to tell someone you’re not interested, so people just disappear. It’s easier than the awkward conversation. It’s easier than disappointing someone. But easy for you creates pain for them. And that can’t keep being normalized.

Here’s what has to change:

If you’re upset about being ghosted, look at where you’re ghosting others. Where are you avoiding difficult conversations? Where are you vanishing when things get awkward? Everyone has to be part of the solution.

In 2026, ghosting isn’t okay. If someone ghosts you, name it. Tell them it hurt. Tell them it wasn’t okay. If you catch yourself about to ghost, have the conversation instead.

Accountability changes everything. Real connection starts with real honesty. And honesty sometimes means the hard conversation instead of the silent exit.

The Year of All or Nothing Isn’t About Extremes

It’s about discernment. It’s about boundaries. It’s about singles deciding they’re no longer willing to overinvest in uncertainty while underinvesting in themselves.

We’re moving away from vague possibility.

No more “let them” if you’re not ready to say “F them.” No more potential if you’re not seeing proof. No more maybe if you need to know. The threshold is shifting. And once it does, there’s no going back to the ambiguity.

💌 Got a question about dating intentions, setting boundaries, or navigating relationships in this new era of clarity?

Whether it’s about speaking your hot takes, recognizing effort (or the lack of it), moving away from the texting trap, or learning how to hold yourself and your person accountable, we’re here for all of it.

DM @DamonaHoffman or leave a voicemail or text at 424-246-6255

*Our Instagram and Facebook accounts are currently paused so message us on TikTok, X or YouTube, through the contact form on DamonaHoffman.com, or the number above*

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

Download the free Date Tracker at damonahoffman.com/datetracker. It’s designed to help you see your patterns and move forward with clarity.

 

Why You’re Getting Attention You Didn’t Ask For

If you’re newly single after decades of marriage, the dating landscape probably feels like a foreign country.

The apps. The messaging dynamics. The cultural expectations. Everything’s shifted.

And somewhere between setting up your profile and swiping through a few rounds, you notice something: your inbox is filling up with guys who weren’t even born when you graduated high school.

We hear a lot about men dating younger women. It’s normalized. Expected. The reverse feels confusing, maybe even uncomfortable. Like you’re breaking some unspoken rule just by existing in a dating app at your age and looking the way you do.

The truth is more complicated. And way more interesting.

A listener reached out about exactly this.

She asked:

“I am separated a year in the process of divorce after 29 years of marriage. I am 52 and told that I look a lot younger than my age. On dating apps, I’m getting a hit up by a lot of 30 somethings, and even some late twenties. Is there something going on like cougar? I have very little interest in somebody under the age of 40. Considering I have a 30-year-old myself, I’m just wondering, how do I get men in my age range that would have an interest in me?”

If this resonates with your situation, you’re not alone. Women reentering the dating scene after long marriages are experiencing this exact phenomenon. And the question underneath it all is worth exploring.

(04:20) It’s Not Random. The Algorithm Knows What It’s Doing

Dating apps operate on a simple principle: show people to the users who are most likely to engage with them.

When a profile gets set up with certain photos, certain language, and a certain age, the algorithm starts learning. It learns who clicks. Who messages. Who shows up. And it serves that profile to more of those people.

Some dating apps let users do open searches across ages. 

Some are swipe-based with fuzzy matching on both sides. 

Some even let people pay extra to break through the noise and land in specific DMs. 

So when a woman in her 50s starts seeing a flood of matches from guys in their 30s, it’s rarely random.

The algorithm found them because they fit a profile someone is actively searching for. Whether that’s intentional or not depends on the woman. But the matches themselves? They’re not accidents. They’re the system working exactly as designed.

(07:40) Women in Their 50s Are a High-Risk Target for Scammers

This is the part nobody wants to talk about, but it’s critical.

Women who are 50-plus, recently separated or divorced, and financially stable are literally the profile that scammers look for. They’re fishing in these waters deliberately.

The reasoning is calculated. Scammers may believe awoman who just left a long marriage might be lonely, might be grateful for attention, might be out of practice reading manipulative behavior. She might have resources, property, retirement accounts. She might be eager to believe someone is genuinely interested in her.

Scammers operate from these assumptions. They build profiles designed to catch exactly this person.

The warning signs aren’t about age. They’re about behavior:

• Fast escalation of emotional language or talk of a future together 
• Reasons why they can’t video call or meet in person 
• Stories about financial hardship, emergencies, or needing help 
• Requests for money, favors, or access to information early on 
• Inconsistencies in their story or availability

A 35-year-old can be a scammer. So can a 58-year-old. What matters is whether the person’s actions align with their words. Whether they’re moving toward a real meeting or keeping everything digital and vague.

(09:20) Pop Culture is Telling Us Something’s Shifted

Notice what’s happening in movies and television right now.

Baby Girl is a mainstream theatrical release. Milf Manor is a dating show on a major network. All Fours was a bestselling novel that spent weeks on the New York Times list. These aren’t indie productions or niche content. They’re playing in theaters, streaming on major platforms, being discussed at dinner parties across the country.

Now think back twenty years: The Graduate in the 1970s was basically the only mainstream film that explored an older woman and a younger man, and it was treated as scandalous, transgressive, unusual.

That gap tells a story: Culture doesn’t create these stories in a vacuum. Artists make work about what’s already happening in society.

If there’s a genre of entertainment dedicated to older women dating younger men, it’s because enough women are living that reality that there’s an audience for it. 

Visibility creates legitimacy. And legitimacy makes what felt taboo feel normal.

(15:40) Your Profile Language Determines Who Shows Up

This is the thing that changes everything but gets overlooked.

The words in a dating profile aren’t just a description. They’re a filter. They tell people whether you’re serious or tentative, confident or lost, ready or still figuring it out.

Compare these two profiles:

“I’m new to dating apps and a little nervous. I was married for 30 years so I’m still figuring this out. Please be patient with me.”

vs.

“I’m looking for someone ready to build something real. I know what I want and I’m not settling.”

Both could be written by the same woman. But the first one attracts men who want to rescue her or take advantage of uncertainty. The second one attracts men who are actually looking for a partner, not a project.

Tentative language signals you’re not sure if you belong on the app. Confident language signals you know exactly why you’re there.

When a woman’s profile is clear about her life stage and her intentions, it does the filtering work before the matching even happens. The wrong people self-select out. The right people see themselves in it.

(18:00) Your Divorce Status Might Be More Relevant Than Your Age

A lot of people who are relationship-minded, especially those in their 50s and 60s, have a hard boundary: they won’t date someone who isn’t actually divorced yet.

It’s not judgment. It’s a boundary learned from experience. They’ve been burned before.

They’ve waited for someone to finish their divorce, only to have them get back together with their ex, or drag them through years of legal complications, or realize they weren’t actually over the relationship.

So they made a rule. No dating until papers are signed.

This means that while someone is separated and in the divorce process, they might be narrowing their options without realizing it. The relationship-minded people their age are off the table. The younger people who message them might not have that boundary yet because they haven’t been through it.

This isn’t an argument for dating younger men. It’s an argument for understanding that rushing back into dating while still technically married, even if you’re separated, might be costing her time and options without her realizing it.

What if the real permission she needs isn’t permission to date. It’s permission to wait. To take time figuring out who she is when she’s not a wife. To explore what she actually wants without the pressure to couple up again.

The matches will still be there when the divorce is final. And she’ll be so much clearer about what she’s actually looking for.

(26:00) The Hidden Thing That Actually Attracts People

Let’s talk about flexibility. Not physical flexibility. Emotional flexibility. Life flexibility.

The willingness to change your routines. The openness to someone new disrupting your schedule. The ability to evolve instead of staying locked in a particular way of doing things.

By the time people hit their 50s, a lot of them have stopped evolving. 

• They know what they like. 
• They know how they do things. 
• They’re looking for someone who will fit into the life they’ve already built, not someone who will ask them to change.

But a woman who just got divorced from a 30-year marriage isn’t in that place. She’s rebuilding. She’s figuring out who she is when she’s not following someone else’s script. She’s open to new things because everything is new right now.

That openness is magnetic. It has nothing to do with age and everything to do with energy.

A man looking for someone who’s alive and interested in possibility will see that. A man looking for someone to maintain the status quo won’t.

The real work isn’t about filtering for the right age. It’s about getting clear on who you actually are now and what you actually want. That clarity, that aliveness, that flexibility: that’s what attracts the right people, whatever their age.

 

💌 Navigating age gaps after decades of marriage, wondering about cougar culture, or just trying to figure out what’s next?

Whether it’s about protecting yourself from scammers, understanding your own boundaries, or getting clear on what you actually want, we’re here for all of it.

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

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

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

 

The holidays have a way of forcing conversations you’ve been putting off.

You’ve been dating him for ten months. Things are getting serious. You’ve met his five-year-old son multiple times. But your family still doesn’t know he has a kid. And now the holidays are here, and he wants to bring his son to your family dinner.

Suddenly the “right moment” you’ve been waiting for has arrived whether you’re ready or not.

This week, a listener named Kayla reached out about this exact collision: a relationship that’s getting real, a secret that’s gotten too heavy to carry, and a holiday deadline that won’t wait.

She shared:

“I’ve been dating this guy for 10 months now and things are really getting serious between us. He has a five-year-old son from a previous relationship, and I’ve met him a few times. He’s a great kid. I really care about both of them. But here’s where I’m stuck. My family’s having their big holiday dinner, and now my boyfriend wants to come. He wants to bring his son. Part of me loves that. But I haven’t told my parents he has a kid yet. I know I should have mentioned it earlier, but it felt too soon, and now it feels too late. Do I tell them before he comes or should I tell him to come next year instead? I really feel like this guy could be the one, and I don’t wanna mess this up.”

This is a question that goes deeper than holiday logistics: Can I commit to this relationship and everything it actually includes?

(02:40) The Omission Itself Has Become the Problem

Here’s the truth sitting underneath all of this: the silence has become bigger than the secret.

When you keep something significant hidden, silence creates its own story. Your parents will wonder why you kept this from them. And the longer information sits unspoken, the more weight it takes on, even when it really shouldn’t be that big of a deal.

What you’re really carrying right now:

• The guilt of not mentioning it when it mattered
• The growing anxiety about the reveal
• The fear that naming it makes it feel more serious
• The weight of compartmentalization itself

Every day that passes, that load gets harder to carry.

(03:20) If There Were No Deadline, Would You Still Be Avoiding This?

That’s the real question.

The holidays aren’t creating the problem. They’re just creating artificial urgency around a conversation that probably should have happened months ago, back when you met his son or when it started to seem serious.

You need to separate the holiday pressure from the relationship reality. Ask yourself this: If you’re not comfortable telling your family that he has a child, why? Is it your parents’ expectations, or is it your own?

Sometimes that fairytale we’re protecting is actually the one we’ve been writing in our own heads. Maybe it includes a fear of letting him down. A fear of letting his son down. A fear of suddenly becoming a mom when that wasn’t on your life path before.

This isn’t about whether you should tell them. It’s about whether you are fully ready to commit to this relationship and everything that it includes.

(06:00) This Isn’t Halfway In Territory

Ten months in, you’re not in “let’s see how it goes” anymore.

When you are dating somebody with a child, especially a five-year-old, this means you’re accepting a possible outcome where you’re going to be in this kid’s life. For a very long time. And you likely would be part of raising this kid in some way.

That’s the really big question that has to be answered at the beginning: Am I really okay with this?

Here’s what we hear from people: 

“I don’t see myself dating someone with a kid.” 

“I don’t really wanna deal with any baby mamas.” 

But here’s the reality: Love is love. 

You can’t control what somebody’s backstory is. Your boyfriend did not intend to have a child and then have a breakup. These aren’t experiences people go out seeking. Yet they become part of our story.

When you’re in a relationship with somebody who has a more complicated story, you have to consider how to reframe your own expectations. This could be a wonderful thing he’s bringing into your life. And there may also be an adjustment period as you grapple with what is and how you wished it would be.

(09:00) First and Foremost: Do Right By the Child

There’s a child involved here, and that changes everything.

This isn’t just about your relationship with your boyfriend. It’s about a five-year-old who’s already met you multiple times and knows you exist in his life. If things are serious enough that you’re considering family holiday gatherings, they’re serious enough that this child matters.

You have a responsibility here. If you really feel like he’s the one, you want to show him that you’re accepting of all of the parts of him and his life, especially someone as important as his son.

What does doing right by that child actually look like:

• Being honest about the relationship instead of keeping him a secret
• Showing up as someone stable and present, not someone hiding
• Integrating into his life in a way that’s real, not compartmentalized
• Being willing to step into whatever role this becomes

First and foremost, you have to do right by that child. Not eventually. Now.

(10:40) The Holiday Isn’t Actually the Problem

You’re asking me if you should push this off until next year. But here’s the thing: there’s no perfect time. Actually, the holidays might not be the worst time.

Having everybody gathered and having it be a big family experience, it sort of just drops him right into the fast lane. You don’t have to go through introducing him one by one. Everybody’s here. He gets to know them in little bites, in small bursts. In a big gathering, it’s sometimes easier for him to figure out where he fits within the family order.

But you absolutely cannot show up with a surprise child at the holiday dinner. Your fear of their reaction is valid. But it’s not a reason to ambush them or keep living with a secret.

Telling your parents now, not tomorrow, not just showing up:

• Gives them time to process
• Shows them respect
• Allows them to do a rewrite of their own story

You also can’t put your boyfriend in a weird position. Where he has to ask his ex to take the kid for the holidays so he can go with you. That’s just way too complicated. And it signals to him that you’re not fully in.

(13:00) The Door Is Being Opened

If you rescind the offer to your boyfriend, the one you said could be the one, what message does that send? Does it make him feel like he’s on that trajectory with you? Or does it make him feel like he’s being put off or let down easy or hidden?

Big events can be scary. Big life transitions can be scary. Claiming someone and declaring your intent in a relationship can be a lot.

But you know the best thing to do.

There’s a moment being created for you right here. The door is being opened. You have a choice. And it may be time for you to just bravely walk through it.

The gift you give yourself and everyone else is the truth, even when it’s uncomfortable. Especially when it’s uncomfortable.

💌 Got a question about blended families, telling your family something you’ve been hiding, or conversations you’ve been avoiding?

Whether it’s about introducing a partner with a child, managing family reactions to complicated relationships, figuring out if you’re truly ready to integrate someone into your life, or just needing permission to have the hard conversation, send it our way.

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

And remember: Dates & Mates covers all the significant relationships in your life. Your romantic partners. Your family dynamics. Your own readiness to step up. And most importantly, the courage underneath your hesitation.

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

When Your Person Gets a Person, Why Does Romance Always Win?

Have you ever watched your best friend disappear into a new relationship? Do you find yourself wondering why six years of daily connection suddenly counts for less than six weeks of dating someone new?

You’ve felt this before: When the person who used to be your first call becomes someone you have to schedule weeks in advance, when the standing plans get cancelled. When the texts just stop coming.

We’ve been told our whole lives that romantic love comes first. That, of course, a boyfriend or girlfriend takes priority; this is just how it works when people couple up.

IRL, some of the deepest, most committed, most sacred relationships we build are with our friends. And when those get dismantled because romance showed up, the loss is real. The grief is valid. And the silence around it makes it so much worse.

It’s about hierarchy, how we value different kinds of love, and whether you’re allowed to speak up when the relationship that feels like family to you gets downgraded to an afterthought.

A listener named Sarah sent a question about a situation that so many of us are navigating right now:

“My best friend and I have been inseparable for six years. We talk every day, we’re each other’s emergency contacts, and honestly, she feels more like family than my actual family. But lately her new boyfriend has been making comments about how ‘codependent’ we are and how she needs to ‘prioritize him now.’ She’s starting to pull back and it’s breaking my heart. Am I wrong to feel like she’s my person? Why does romantic love automatically rank higher than friendship love? How do I communicate to her that what we have matters just as much without sounding jealous or clingy?”

This is a question that goes deeper than one friendship: can I advocate for what we’ve built without being dismissed as needy?

(03:00) The Cultural Hierarchy We All Bought Into

Why does romantic love automatically rank higher than friendship? That is the question.

Here’s something you need to hear: You are not wrong for asking.

We live in a culture where romantic partnership sits at the top and everything else (friendships, chosen family, platonic bonds) is supposed to move aside when romance shows up. 

It’s reinforced by:

• Weddings and marriage ceremonies that center one relationship above all others
• Tax structures that benefit romantic partnerships
• Cultural narratives that make romantic love the “ultimate” goal

There’s a concept called Relationship Anarchy that flips this whole script. Instead of automatically putting romantic love at the top of the pyramid, what if we stopped ranking our relationships at all?

Because putting all our eggs in that romantic love basket? That’s part of the fairy tale that keeps us believing one person should meet all our needs. It’s unrealistic, and when you pull away from relationships that were working just because they’re not romantic, it’s devastating.

(06:00) Your Friend Is on Drugs (No Really)

You have to tread carefully because your friend right now is on drugs. Like, literally on drugs.

The love hormones, that cocktail of neurotransmitters that hits when you’re first in romantic love? That’s powerful stuff.

If you’ve ever known anyone on drugs, sometimes they’re not very nice people. They don’t think about the consequences of their choices and actions. That’s what’s happening right now.

Here’s the reality: Healthy partners integrate. They don’t just downgrade other relationships.

And this pattern happens everywhere:

• When your new boss expects you to drop everything for work
• When a family member demands you choose sides
• When anyone decides their relationship with you should eclipse all your other connections

(10:00) What You Can Change (And What You Can’t)

There’s not much you can do to alter her relationship with her partner. You’re pretty powerless there.

But you do have more power than you probably feel right now in how you proceed in your relationship with her.

Let’s talk about what you’re feeling: There’s likely a sense of grief because you’ve lost consistency. You’ve lost that sense of security.

She was literally your emergency contact and now you’re wondering: can I count on you?

That’s what’s underneath all of this. Can I still count on this person I’ve trusted? That feeling is totally valid.

You have to acknowledge that grief, and then you need to do something about it.

(12:00) The Trap That Keeps You Silent

This is the trap that keeps so many people silent when their most important relationships are being dismantled.

We’ve been taught that if we speak up about our relationship mattering or about what we need, we’re going to get labeled. Someone’s going to withdraw their love.

Here’s the reframe: Advocating for an important relationship is honest, not clingy. Expressing hurt is vulnerable, not jealous.

You have a right to say: Our friendship matters, and it’s changing in ways that hurt me. That’s caring, not clingy.

Start with curiosity: Sit her down and lead with: “I’ve noticed things feel different, and I miss you.”

When you lead with curiosity in any relationship, it opens the door rather than shutting it. Name your feelings without assumptions: “I’m really feeling upset about our friendship shifting. Are you feeling it too?”

(16:00) The Negotiation (Because Change Is the Only Constant)

She might not fight for this friendship the way you would. Your job is to decide how much space to hold for someone who’s making you feel smaller right now.

There’s also a reality to prepare for: Less time, less of your friend’s emotional pie to go around.

Daily texts might not be possible, but:

• Could it be weekly texts?
• A standing dinner once a month?
• Check-ins when either of you really needs support?

It’s a negotiation. What do you need right now? What is your friend able to give?

The only constant thing in life is change. If this relationship is changing, how are you going to evolve yourself? Can you explore new interests? Invest more in other friendships?

Being adaptable is the most vital skill for connection in today’s world.

Love is a web of connections, and every thread matters.

When you’ve built six years of showing up, of being each other’s emergency contacts, of creating family where biology didn’t provide it? That’s not less than romance. That’s not second place.

Speaking up for the relationships that matter isn’t selfish. It’s necessary.

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

Whether it’s about speaking up when you’re being pushed aside, figuring out what you’ll accept when someone’s time gets divided, or learning how to advocate for non-romantic relationships without being labeled clingy, 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 covers every relationship that shapes your world: your best friends, your romantic partners, your chosen family, your colleagues, and most importantly, 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

 

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